A Look at NHL Playoff Droughts Part 5: Ottawa to St. Louis

Not everyone can make the postseason. Every season sees teams end their season with their final regular season game. Some teams miss it more than others and for some long periods of time. The New Jersey Devils, for example, have missed the playoffs for four straight seasons now. Some of the People Who Matter claim that this is necessary. The result of a rebuild; a price to pay now for setting up a team for future prizes. Is that really true though? And how does this current drought for the Devils compare with other NHL teams? What can we learn from other droughts in NHL history? To answer these questions and more, let us take a deeper dive into playoff droughts among the NHL franchise.

This is a multi-part series covering the active franchises in the NHL and their significant runs of futility except for the recent teams in Las Vegas and Seattle. In Part 1, I covered the scope of this project, acknowledgments about the differences in NHL league structures and eras, and the first set of teams: the New Jersey Devils, Anaheim, Arizona, Boston, and Buffalo. Please review Part 1 if you have any questions with how I am approaching this issue. Part 2 covered the C-teams: Calgary, Carolina, Chicago, Colorado, and Columbus. Part 3 went over Dallas, Detroit, Edmonton, Florida, and Los Angeles. Part 4 detailed droughts by Minnesota, Montreal, Nashville, the New York Islanders (a.k.a. Milbury!), and Our Hated Rivals (a.k.a. Smith/Sather!). This part will go over the Ottawa Senators, the Philadelphia Flyers, the Pittsburgh Penguins, the San Jose Sharks, and the St. Louis Blues. The goal remains: to learn from what they suffered from and how they got out of it. Here is a chart of the five teams in this post of their total frequency of droughts with the Devils’ own history of playoff droughts included for reference purposes (it is a Devils site, after all).

As ever, I want to thank Hockey Reference, HockeyDB, Elite Prospects, NHL Trade Tracker, and other sources as needed for information.

The Playoff Drought Chart - Part 5

Hockey Reference

The Ottawa Senators

Playoff Misses and Proportion: 13 misses out of 29 total seasons; 44.8% missed.

Current Situation: The Senators are currently in their longest playoff drought in franchise history of five seasons and running. The Senators finished seventh in the Atlantic Division last season with a record of 33-42-7 for 73 points, right behind Detroit and Buffalo. With a points percentage of 44.5%, it was their best season out of the last five seasons that make up this current drought.

A Summary of a Notable Drought: Back in Part 1, I covered Buffalo’s current drought. I had to. Buffalo’s 11-seasons-and-counting streak of missing the playoffs is the longest in NHL history. A root of that drought is ownership. Ottawa has not been in the league as long as Buffalo and their current drought is just below half of their length. But I will cover it here as it is another example of ownership either directly or indirectly held the team back.

A quick word on said ownership for Ottawa. Eugene Melnyk. He passed away earlier this year and so I do not intend to speak ill of the deceased. As much criticism he will get, both direct and indirect, there are no Ottawa Senators without him. Rod Bryden took over the Senators just before the 1993-94 season from a group led by Bruce Firestone. In the early 2000s and in the wake of a weakening Canadian dollar, the Senators were financially insecure. Bryden requested tax relief for the Senators and other Canadian NHL teams from the Canadian government; but the program was cancelled. A A sale to a limited partnership fell through. In early 2003, the Senators entered bankruptcy protection and needed emergency funds to keep running. (Yes, the 2002-03 Senators that the Devils beat in the ECFs. That one was in dire straits). Ultimately, Melnyk came in the Summer and purchased the team in August. He had the cash to secure the team financially and the desire to keep the team in Ottawa. He also had a keen interest in keeping the Sens on a tight budget (with exceptions) and wanting things done his way. With that in mind, let us go to the season before the drought.

The 2016-17 season for Ottawa was a special one. Pierre Dorion was promoted from assistant GM to GM after Bryan Murray stepped down. 35-year old goaltender Craig Anderson had a wonderful season in a 1A/1B system with Mike Condon, posting a 92.6% save percentage in 40 games. (Condon wasn’t half bad with a 91.4% in 40 games.) New head coach Guy Boucher came in and while the Sens weren’t great in 5-on-5, they weren’t awful either (CF% was below 49%, SF% was just above 50%). While Dorion moved Mika Zibanejad and a second rounder in 2018 to New York for Derick Brassard and a seventh rounder in 2018, the offensive core remained the same. Erik Karlsson had another star-like season with 71 points and was a finalist for the Norris. Mike Hoffman, Kyle Turris, and Mark Stone each put up at least 20 goals and 50 points. Dion Phaneuf and Cody Ceci took on big minutes behind Karlsson. The team started off well and never had a losing record. They added Alex Burrows, Viktor Stalberg, and Jyrki Jokipakka and a second rounder by the deadline in what would be a playoff appearance. The Sens went 44-28-10 for 98 points.

The 2017 playoffs were a magical time for the Sens as they went on a run. They won in six games over Boston with three of Ottawa’s four wins coming in overtime and the fourth was a 1-0 final. Brassard may have had a not-so-hot season, but he was big with 8 points in this season; as was Bobby Ryan with four goals and three assists. In the second round, Ottawa took on the Rangers. This series much more scoring, including a 6-5 Game 2 decided in double OT (by Ottawa), a 5-4 OT Game 5 that saw Ottawa break a 2-2 tie in the series, and 4-2 final. Jean-Gabriel Pageau was hot in this series with 6 goals, finishing just behind Karlsson in total points (Karlsson had 7). In the Eastern Conference Finals, Ottawa took on Pittsburgh. Their first conference finals in a decade and Ottawa struck first in Game 1 in, you guessed it, overtime. It appeared the Penguins woke up after a 5-1 loss in Game 3 and took down Ottawa in Game 4 and blew them away 7-0 in Game 5. But Ottawa pulled out a 2-1 win in Game 6. Game 7 on May 25 had the Senators keeping with the eventual Cup champs. Mark Stone scored 20 seconds after Chris Kunitz opened the scoring. Almost three minutes after Justin Schultz made it 2-1 in the third, Ryan Dzingel tied it up. Anderson and Matt Murray were in a dual. Double overtime was needed and, alas for Ottawa, Kunitz finished the series. The Senators were a goal away from a Stanley Cup Final against Anaheim.

I had to explain all of that to provide the context of what would come next. Logically, if your team finished just shy of 100 points and were a goal away from a championship series, then your team must be pretty good. You figure you may need to retool some things, lock up some players, and perhaps bring in a little more talent to get over the top next season. You would also think the team would have a lot of goodwill. The 2017-18 season showed otherwise.

On paper, the offseason looked fairly OK. Without a lot of picks, their 2018 draft class was just four players: Shane Bowers, Alex Formenton, Drake Batherson, and Jordan Hollett. Long time players Chris Neil and Clarke MacArthur, the latter due to concussions, called it a career. Tommy Wingels and Viktor Stalberg signed elsewhere, while Marc Methot was lost to Las Vegas in the expansion draft. The major free agent signings were Nate Thompson and Johnny Oduya. Dorion opted for re-signing players to keep them; including a $9.5 million, two season extension for Anderson, Mike Condon being signed to $7.2 million over three seasons, and second-round-playoff-hero Pageau a $9.3 million deal over three seasons. Not amazing, but understandable.

There was a bit of a snag, though. You see, the Senators did not sell out all of their playoff games. The Canadian Tire Centre is in Kanata, Ontario, which is a suburb of Ottawa and not the easiest to get to. Still, a Canadian team not selling out in the playoffs is a bad look. Ahead of the season, the team decided to reduce seating in the upper bowl that did not sell out during the playoffs, add in a stage, and even put in tarps. Not a great look, but whatever, it is all about what is on the ice, right?

Additionally, Erik Karlsson needed surgery in the offseason to repair tendons in his left foot. He would miss the start of the season and come back less than 100%. But he was happy to report the announcement of his first child. However, in March, it was revealed the child was stillborn. And, worse, this sad news is relevant to this situation.

Not having Karlsson at the start of the season hurt as he was a crucial player for Ottawa. And essentially running it back with the same core did not work out so well again. The team started off not as hot as last season with a 5-2-5 record. Early signs that the 36-year old Anderson was going to play like, well, a 36-year old not-legendary goaltender. No matter, Dorion had a plan. Matt Duchene wanted out from the Avalanche. There were some unhappy Senators to move. Negotiations with Kyle Turris to lock him up were not going well. Andrew Hammond was toiling in the AHL as Anderson and Condon effectively took the net last season. Dorion figured the solution to his problems plus improving the team was right there. So on November 5, he traded Turris, Hammond, Bowers (the first round pick in 2018), a conditional first rounder in 2018, and a third rounder in 2019 to Colorado for Duchene. The trade was a three-team trade as Turris ended up with Nashville, who sent their second, Samuel Girard, and Vladislav Kamenev to Colorado for him. The Senators now had Duchene join Karlsson, Stone, and Hoffman as offensive leaders. Good, right?

Not good. The team cratered for the next three months. Anderson would end up finishing the season with an 89.8% save percentage in the 58 games he would play in. Condon would get into 31 games and not fare much better with a 90.2% save percentage. Ottawa went from a near-top team in goals allowed to next to worst in the NHL in just one season. While Duchene did provide 23 goals and 49 points in 68 games, Stone put up 20 goals and 62 points to lead the team in scoring, and Karlsson would put up 62 points in 71 games, the offense as a whole took a step back. Brassard and Ryan did not crack 40 points, Pageau brought in just 14 goals and 29 points. Burrows just added 14 points in 71 games. The team was well outside of the playoff picture before the February 26, 2018 trade deadline. Dorion thought to sell.

Meanwhile, fans wanted Melnyk to sell. While this season was going on, Melnyk hardly covered himself in glory. As it was the NHL’s centennial season, a special outdoor game was held between Ottawa and Montreal in December. Melnyk took part in the festivities and decided it was an early Festivus and so he aired some grievances. The day before the big game on December 16, Melnyk implied the team could be relocated, criticized the fans for not buying enough tickets, insisted he spent enough on player salaries (keep this in mind for the next few seasons), noted that everything else was running on a “shoestring budget,” and took a shot at the National Capital Commission over the LeBreton Flats negotiations - an area of land that Melnyk wanted for a new arena to keep the Senators in Ottawa and get them out of Kanata. Goodness, Melnyk, tell us how you really felt. Between this, tarps in the arena, and the team cratering after a great 2016-17 season, fans were getting fed up.

Additionally, in February, team president Tom Anselmi resigned without notice - which was the second high-profile front office departure since Daniel Alfredsson left the organization in July. In a move befitting of shoestring budgets, Melnyk extended Dorion for another three seasons and gave him a new task in light of the team’s terrible season and Melnyk’s suggestions he had to cut salaries from the payroll. In other words, rebuild.

Dorion followed directions in February 2018. Dion Phaneuf and Nate Thompson were sent to Los Angeles for Marian Gaborik and Nick Shore. Brassard, who was acquired last season for Zibanejad (oof), was sent to Las Vegas for Pittsburgh’s third rounder in 2019. Prospect Vince Dunn and a third in 2018 were sent to Pittsburgh for Ian Cole, Filip Gustavsson, and their first in 2018. Cole was flipped to Columbus three days later for Nick Moutrey and a third in 2020. Shore was sent to Calgary for a seventh rounder in 2019 and, on the same day, lost Johnny Oduya - one of Dorion’s free agent signings - to waivers. It was not massive, but a rebuild was beginning as the team sputtered to a 28-43-11 record for 67 points. A drop of 31 points, an arena temporarily blocked off due to a lack of ticket sales, a goaltending tandem that aged like milk after getting re-signed, and an owner who took shots at the fans and the people he needed for the new arena he wanted. What could be worse?

How about a fan campaign of #MelnykOut? How about Dorion telling teams before the deadline that Karlsson could be available and then Dorion claiming an eight-season extension will be offered in the offseason? How the aforementioned Alfredsson - a beloved figure among the Senators fans - going to the media about how he hopes for a new owner? How about an assistant GM accused of harassing a hotel shuttle driver at the NHL Draft combine (he would resign in August)? How about a locker room issue no one would wish on anyone? All of that would happen and I cannot ignore the latter.

Back in March, Erik and his wife, Melinda, announced that their first child was stillborn. In May, Melinda went to court and applied a peace bond (a kind of protection order) alleging that Monika Caryk posted hundreds of offensive messages online about her, her husband, and her unborn child. Caryk was Mike Hoffman’s girlfriend. The news came out on June 12 and this would lead to further legal proceedings between Melinda Karlsson and Monika Caryk. With respect to the Senators, this news meant that either Karlsson or Hoffman had to go. If only to maintain any kind of peace in the organization, much less try to keep Karlsson from walking before he could hit free agency in 2019. This led to Dorion trading Hoffman, Cody Donaghey, and a fifth in 2020 to San Jose for Mikkel Boedker, Julius Bergman, and a sixth in 2020 on June 19 - a week after the Toronto Star broke the story about Monika Caryk.

The 2018 NHL Draft would prove fruitful for Ottawa as they took Brady Tkachuk at fourth overall. They flipped Pittsburgh’s first to the Rangers for Boston’s first and New Jersey’s second, taking Jacob Bernard-Docker and Jonny Tychonick with those picks. The offseason proved quiet for the rebuilding, not-spending Senators. Alex Burrows was bought out. Stone (for $7.3 million, avoiding arbitration), Ceci (who did go to arbitration and got a $4.3 million deal), Nick Paul, and Chris Wideman were all re-signed for a season. Their biggest free agent signing may have been Mike McKenna. Surprisingly, Tkachuk signed an ELC and would turn pro for 2018-19.

Then it all dropped in September. Dorion would trade Erik Karlsson after all. While the team did offer an extension, the negotiations for said extension did not go well. Just before training camp, the Senators sent Karlsson (and Francis Perron) to San Jose for the following: Josh Norris, Dylan DeMelo, Rudolfs Balcers, Chris Tierney, San Jose’s first in 2019 or 2020, a second rounder in 2019 (either San jose’s or Florida’s, which ever was higher), and two conditional picks based on what the Sharks do with Karlsson. The official announcement headlined it as “Ottawa Senators complete most important trade in rebuild.” As if there was any doubt what the Senators were doing. This still stunned the fans (and perhaps the team) that the Senators traded away the best player they had in the 2010s and among the best they ever had.

This may shock you, but there would be more departures from that 2016-17 squad that was just a goal away from the Finals. Mark Stone would be sent to Las Vegas by the deadline with Tobias Lindberg for Erik Brannstrom, Oscar Lindberg, and Dallas’ second rounder in 2020. Stone still ended up leading the Sens in scoring that season despite the trade. Ryan Dzingel had a 22-goal season and counting in Ottawa. He and Calgary’s seventh rounder was sent to Columbus for Anthony Duclair and two second round picks. Matt Duchene, the result of the big trade Dorion made last season, was sent off with Bergman to Columbus for Vitaly Abramov, Jonathan Davidsson, and two conditional first rounders. Meanwhile, the return from the Karlsson trade was not exactly productive. Tierney put up 48 points, which was nice. Balcers put up 14 points in 36 games, which was not. DeMelo put up 22 points on a beleaguered blueline. The team’s youth were starting to emerge on the roster as Tkachuk spent his first pro season in Ottawa for 22 goals and 45 assists; Thomas Chabot broke out as a new leader on the blueline and productive with 55 points in 70 games; Colin White put up 41 points; and other youngsters appeared from Batherson to Max Veronneau to Christian Wolanin to Balcers to Duclair to Maxime Lajoie. At least it was looking like a common rebuild.

There was little question who ordered this: Melnyk. In fact, he was public about all this. He stated in February 2019 that “the Senators rebuild plan will take another season or two from now.” The statement included this bold proclamation: “The Senators will be all-in again for a five-year run of unparalleled success – where the team will plan to spend close to the NHL salary cap every year from 2021 to 2025” I will spoil this for you: It would take more than another two seasons and the Senators were not a cap team in 2021 and are not even a cap team as of this writing. Still, this drove Dorion’s actions as you would expect. When the owner says to do something, then his staff does it. The GM answers to him, after all.

As you may expect from this approach, the team was getting wrecked regularly during this tear-down. The Sens finished dead last in goals allowed, no thanks to Anderson putting up a 90.3% in 50 games in his 37-year old season, Condon getting into just two games and giving up eight goals in them, McKenna putting up an 89.7% in 10 games before being dealt with Tom Pyatt and a sixth to Vancouver for Anders Nilsson and Darren Archibald. Nilsson ended up being the team’s best goalie with a 91.4% in 24 games. But the team was getting rolled over in 5-on-5 so he got shelled regardless. After a 22-37-5 record under Boucher, he was fired and his assistant, Marc Crawford, took over to carry the team to a 7-10-1 finish. They finished with 64 points.

The rebuilding would continue in the 2019 offseason. Free agent signings were not impressive on paper as their biggest names was signing veterans Ron Hainsey and Tyler Ennis. Trades were absolutely on the menu, though. July 1 featured a big one. The Sens sent Cody Ceci, Ben Harpur, Aaron Luchuk, and Columbus’ third rounder in 2020 for Connor Brown, Nikita Zaitsev, and Michael Carcone. Later in July, Zach Smith was sent to Chicago straight up for Artem Anisimov. By the end of July, Mike Condon and a sixth in 2020 was sent to Tampa Bay for Ryan Callahan and a fifth rounder. At least Dorion was weaponizing that cap. He was also planning for the future as he signed Colin White and Thomas Chabot to huge six and eight season extensions, respectively. A new coaching staff was brought in too: D.J. Smith as the head coach with Jack Capuano as an associate coach and David Payne and Bob Jones as assistants. Even though part of their current core was secured, the expectations for 2019-20 were low.

The expectations were right. Once again, Anderson was still a below-average goalie with a 90.2% save percentage in 34 games; Nilsson was not much better with a 90.8% in 20 games; and Marcus Hogberg put up a 90.4% in 24 games. The Sens were still near the bottom of the NHL in goals allowed. Scoring was not too much better. Tkachuk and Brown (yes, from the trade) cracked 40 points before the pandemic ended the season with Chabot and Tierney coming close. Ennis provided 33 points in 61 games, Anisimov put up 15 goals and 20 points in 49 games, Duclair put up 23 goals and 40 points in 66 games, and an acquired Vladislav Namestnikov put up 13 goals and 25 points in 54 games. The scoring was still lacking a bit, but it was a bit better. As was the 5-on-5 play. Yet, Dorion went to work selling what he could for a greater tomorrow. All in February before the pandemic-end: Dylan DeMelo was sent to Winnipeg for a third rounder; Pageau (who was having a good season) was sent to Long Island for a first in 2020 or 2021, a second rounder in 2020, and a conditional third in 2021; Namestnikov went to Colorado for a fourth in 2021; and Ennis was sent to Edmonton for a fifth. Dorion had heaps of picks as the Sens missed out on the Return to Play tournament with a record of 25-34-12. At least they were on pace to beat last season’s record of 64 points.

Ahead of the 56-game 2021 season, more was even done to move on from the past. Despite the lack of certainty of a season then, Dorion continued to work. Dorion would not re-sign Anderson and would buy out Bobby Ryan’s contract. Anderson would sign with Washington in January 2021 and Ryan would go to Detroit in October 2020. Boedker would sign in Switzerland, Mark Borowiecki would go to Nashville, and Duclair would sign with Florida. Dorion did spend some money in signing Evgenii Dadonov, Matt Murray, and Alex Galchenyuk while re-signing Connor Brown and Chris Tierney. At the 2020 NHL Draft, Ottawa drafted Tim Stutzle and Jake Sanderson at third and fifth overall among other players. Stutzle would sign an ELC before the 2021 season. Trades? Plenty of them. He took Murray from Pittsburgh in exchange for Jon Gruden and Columbus’ second rounder in 2020. He took on Erik Gudbranson’s deal from Anaheim for Edmonton’s fifth rounder in 20201. He took on Austin Watson from Nashville for Colorado’s fourth rounder. He took on Derek Stepan from Arizona for Columbus’ second rounder in 2021. Marian Gaborik and Anders Nilsson were traded to Tampa Bay for Braydon Coburn, Cedric Paquette, and Tampa Bay’s second rounder in 2022. The youth movement of the Senators was still on. As was the not-be-a-cap-team movement despite proclaiming otherwise in 2019.

Despite a different starting goaltender, the crease was still the same sad story. Murray was not good with an 89.3% save percentage in 27 games. Injuries to Murray, Hogberg, and Anton Forsberg forced call-ups from Filip Gustavsson and Joey Daccord. Gustavsson and Forsberg were the only goalies to post a save percentage above 90% all season - and they played just 9 and 8 games respectively. Once again, the Sens were near the bottom of the league in terms of goals allowed. Up front, the future was brighter. Tkachuk, Brown, Josh Norris, Drake Batherson, and Chabot all put up over 30 points in the shortened season. Stutzle put up 12 goals and 29 points in his rookie campaign. Dadonov only added 13 goals and 20 points while players like Tierney, White, Watson, and Paul did not contribute a lot of production. Anisimov, Stephan, Gudbranson, Galchenyuk, Paquette and Coburn added little. Still, the breakouts of Batherson, Norris, and Stutzle were a reason for optimism. The team still finished well outside of the playoffs with 51 points earned (23-28-5), but not last in the all Canadian division and just nine points outside of the playoffs. There was at least a hint of progress.

The Sens were still sellers throughout the season. Lajoie was sent away to Carolina, Christian Jaros was sent to San Jose, Galchenyuk and Paquette were sent to Carolina for a return of Ryan Dzingel, Braydon Coburn was sent to the Islanders for a seventh in 2022, and Gudbranson was sent to Nashville for Brandon Fortunato and a seventh in 2023. Dorion even bought out Filip Chlapik during the season, allowing him to sign with Pelicans in the Liiga. At least Dorion moved on from the acquisitions that did not perform fairly quickly. Only the Murray deal looked rough given it was a four-season deal to strengthen the goaltending and he played like he was Craig Anderson in disguise.

In the 2021 offseason, Dorion would see even more changes. Colin White and his contract were bought out. Dzingel, Stepan, and Anisimov signed elsewhere whereas Joey Daccord was picked by Seattle in the expansion draft. Dorion returned to smaller, more minor signings in free agency, picking up Michael Del Zotto, Scott Sabourin, and Ennis from the market. The bigger deals were handed out internally with Gustavsson retained for two seasons, Batherson extended for six seasons and Tkachuk extended for seven seasons. By now, the new core of the Senators would include Chabot, Tkachuk, and Batherson. Of course, more trades were made. Dadonov was sent to Las Vegas for Nick Holden and a third rounder in 2022; and 2016 first rounder Logan Brown and a conditional fourth rounder in 2022 was sent to St. Louis for Zach Sanford. Not as expansive as past offseasons, but still notable moves.

The 2021-22 season would confirm Dorion’s bets on Tkachuk and Batherson to be well placed. Batherson could only play 46 games due to injury, but he put up 17 goals and 44 points with it. Tkachuk led the team in scoring again with 30 goals and 67 points. Stutzle and Norris had excellent second seasons. The latter, with 35 goals and 55 points, yielded a huge contract extension earlier this summer, making him part of the core. Holden would end up third on the team in average ice time among defensemen, behind both Chabot and Artem Zub and just ahead of Erik Brannstrom. Goaltending was a bit better in this season as D.J. Smith gavemore games to Forsberg than Murray. Forsberg put up a 91.7% save percentage in 46 games, whereas Murray posted a 90.6% in 27 games (Murray did miss the end of the season with a neck injury). Gustavsson did get 18 games but struggled given his 89.2% save percentage. The Senators were no longer last or next to last in goals allowed, although they were still below the league median. The offensive production was still quite low, helped in part by the team being outplayed in general in 5-on-5. Regardless, the Senators put up their best record since the 2016-17 season: a 33-42-7 mark with 73 points. This included a November where they won one out of twelve games and a March where they went 4-10-1.

This did not stop Dorion from making more moves as a selling team by the deadline. They sent Nick Paul to Tampa Bay for Mathieu Joseph and a fourth rounder in 2024. They sent Zach Sanford to Winnipeg for a fifth rounder in 2022. They sent Josh Brown and a conditional seventh rounder to Boston for Zach Senyshyn and a fifth rounder in 2022. Dorion did make a “buying” move: Travis Hamonic in exchange for Ottawa giving back Vancouver’s third rounder in 2022. Nothing to upset the core, but space made for the future nonetheless.

The worst news of the season came on March 28, 2022. Melnyk passed away due to illness. While his reputation and public statements were negative by the end, Melnyk truly did want a winning team in Ottawa and the team to stay in Ottawa. As stated earlier, there would be no Senators as we know it if he did not step in to buy the team back in 2003. And for his perceived and real cheapness, the extensions given out to Chabot, Tkachuk, White (which was bought out), and Batherson showed a real commitment to the rebuilding effort. It is a shame that, among other things, he will not be able to witness a Senators team perceived to be on the rise.

I would be remiss to point out that after his passing, there has been movement for the two key objectives for the Senators. The first is securing their place in Ottawa with a new arena. In June, the National Capital Commission did accept Ottawa’s proposal for a new arena in Lebreton Flats. While the arena still needs to be built and agreements need to be signed, the work went into getting an arena in that location of Ottawa did pay off. The second is that the Senators would become bigger spenders. OK, not up to the salary cap unless Dorion gives a ton of money to Branstrom and Alex Formenton, who are RFAs who still need new deals as of this writing.

Dorion has been more aggressive in this year’s offseason to improve the team further. He turned Ottawa’s draft capital into a serious player who can help out a lot right away. Prior to the 2022 NHL Draft, Dorion acquired Alex DeBrincat in exchange for Ottawa’s first and second round picks in 2022 and a third in 2023. While this took Ottawa out of fifth overall, they added a 40-goal scorer to a team that has been below league median in goals scored since their last playoff appearance. To add to that, Dorion signed Claude Giroux to a three-season deal worth $19.5 million. Giroux has been a consistent scorer and still has plenty left in the tank; this would not have been a signing made in previous years. And Dorion re-signed Joseph to a four season deal worth $11.8 million and Norris to an eight season deal worth $63.6 million. A move to send Connor Brown to Washington for a second rounder in 2024 was not made due to salary, but due to Brown’s performance in 2021-22 declining from a hot 2021. On paper, the offense should be more threatening.

The other consistent problem throughout this playoff drought has been goaltending. Anderson got old and less effective and Murray has done little to remain as a starting goaltender. The solution: Move on from Murray and get a veteran goaltender with more of a consistent (and better) pedigree. Dorion sent Murray to Toronto and retained part of his salary (yes, Ottawa taking on extra money!) along with a third in 2023 and a seventh in 2024 for future considerations. On that same day, he sent Gustavsson to Minnesota for Cam Talbot.

It remains to be seen whether this all works out. A tandem of Talbot-Forsberg providing at least league average goaltending would be a wonderful turnaround over the last five seasons. The offense providing an offense that at least puts up more than league median in goals would really help them get those few extra wins. Smith will have to manage the squad from getting burned in entire months that end up killing a season, but the squad is, on paper, better than he ever had it. We shall see if 2021-22 turns out to be like 2016-17 where they rise up to a playoff spot after missing out in 2015-16, or if it is just another improvement from 2021-22 but miss out while cracking 80 points.

Any Other Thoughts: There is plenty to take away from an ongoing drought in the league. It is important to have the front office be sorted out. It is important to have an owner not blaming fans or outright saying that he’s paying too much on playing salaries on a bad team. It is important to take care of goaltending, 5-on-5 issues, and offensive attack in order to get wins out of games that would have otherwise had the team fall short. It is important to identify a core of young players who were drafted, pay the ones that prove themselves, and move on from those who struggle or may not be that good. The biggest lesson for me? Accept that just how a team can improve a lot in one season, a team can also fall apart by a large margin. The Ottawa Senators went from a goal in overtime away from a Stanley Cup Final in 2017 to missing the playoffs entirely in 2018 with a team that earned 31 fewer points from the prior season. All with mostly the same core - remember: Duchene was added in 2017-18 - and yet they nosedived. And the drop in quality was ensured by that core either being moved out on the order of ownership or being kept around despite performance issues. I think many of the People Who Matter should recognize that as a warning sign.

The Philadelphia Flyers

Playoff Misses and Proportion: 14 misses out of 54 total seasons; 25.9% missed.

Current Situation: The Flyers have missed the playoffs for the second straight season. After a run where they would alternate playoff and non-playoff years, the Flyers went back-to-back with bad seasons. The 2021-22 Flyers finished with a record of 25-46-11 for 61 points. The 37.2% point percentage makes it the second worst season record in franchise history. The worst was in 2006-07 with a 34.1% (22-48-12) - and weirdly in between two playoff seasons. Neither will be covered in the next section.

A Summary of a Notable Drought: Not all extended playoff droughts feature teams that were awful or trying to avoid a costly rebuild. A team that just continues to fall short can do so for multiple seasons. This does not mean the team does not eventually do something drastic even if their issues boiled down to circumstances and/or goaltending. Such is the story of the Philadelphia Flyers from 1989-90 to 1993-94.

For most of the 1980s, the Flyers were pretty good. They had five 100+ point seasons from 1979-80 through 1989-90. They came in first place in the Patrick Division in each of those seasons. They even went to four Prince of Wales (read: East) Conference Finals and three Stanley Cup Finals in this time period. Of course, they lost all three: the Islanders in 1980, the Oilers in 1985, and the Oilers in 1987. In the high-scoring 1980s when league average save percentages were below 88% in some seasons, the Flyers were doing quite well to hang with the league.

The 1987-88 season seemed like a blip of a season. A season where things went wrong but could be salvaged. Ron Hextall served an eight game suspension from the 1987 Stanley Cup Finals, but still played in 62 games and posted up an 88.6% save percentage. League average in that season was 87.8%, so that was actually fine. Top scorer Tim Kerr missed nearly the entire season with injury; he played in just eight games. Some players had some drops in production like Peter Zezel (72 to 57), Dave Poulin (70 to 51), and Pelle Eklund (55 to 42). Others did break out like Murray Craven, Scott Mellanby, and Rick Tocchet, and the team still got good seasons out Mark Howe and Brian Propp. The Flyers started off the season poorly, suffered plenty of injuries, but still finished second in the Patrick with a 38-33-9 record for 85 points. They made the playoffs. They were eliminated by Washington in seven games, which was worse than it seems. The Flyers went up 3-1 in the series before losing 4-3 to the Capitals. And in Game 7, they choked a 3-0 lead to Washington in the second period, needed Brad Marsh to score his first playoff goal of the series to tie the game at 4 in the third, and lost to Dale Hunter in overtime. GM Bobby Clarke was very unhappy at this and fired head coach Mike Keenan over it.

OK, so they made the playoffs in 1987-88 with 85 points. But the team declined further in 1988-89. Paul Holmgren was hired to replace Keenan as the head coach. Again, Hextall posted an 89.1% save percentage in a league where 87.7% was the average for that season. So the Flyers were one of the better teams in terms of allowing goals. The team’s offense was rejuvenated as they scored 307 goals. Tim Kerr was healthy and put up 48 goals and 88 points. Tocchet put up 45 goals. Propp put up 32. A youth movement of Mellanby, Ron Sutter, Craven, Eklund, Terry Carkner and Gord Murphy continued to perform. Yet, the team struggled with consistency in games. They finished with a record of 36-36-8 for 80 points and took the final playoff spot in the Patrick Division with a fourth place finish. The Flyers were never in danger of falling out of a playoff spot. And the team went on a run in the postseason. They upset the Capitals in the first round for revenge for last year, featuring Hextall scoring a goal. They came from behind to eliminate their rivals, the Penguins, in seven games. They fell to Montreal in the Prince of Wales finals. Despite the average record, one could conclude that the Flyers would keep on keeping on. What was not known that the Game 6 loss on May 11, 1989 would be their last playoff appearance until 1995. And a lot would change from then on.

Now, I want to emphasize that to make the playoffs in this era of the NHL, one had to finish in the top four positions in the division. This allowed some really below mediocre teams to get into the playoffs. It also meant that a strong division could keep out a team that otherwise would have made it through a weaker one.

The 1989-90 Flyers would be not be a victim of those circumstances. Instead, they had a rockier season the last two. Once again, Hextall had to miss the beginning of the season due to violence in the playoffs. However, this season would have Hextall play just 8 games as injuries mounted and he was not good in those 8 games. Goaltending would ultimately be fine as Ken Wregget and Peter Peeters - signed in the offseason, sent with Keith Acton to Winnipeg for future considerations, and re-acquired from Winnipeg with Keith Acton for the cost of Toronto’s fifth rounder in 1991 a few days later (really, Clarke?) - posted save percentages above the league average of 87.8%. The offense was not bad at all as they did combine for 290 goals. Tochett put up 37 while six other players put up at least 20 goals. However, all was not well. Due to the team suffering multiple losing streaks, Dave Poulin was stripped of the ‘C’ and traded for Ken Linseman in January. Despite being a consistent scorer, Propp was struggling this season with just 28 points in 40 points. He was sent to Boston for a second rounder in 1990. Kerr missed much of the season again with injury, but he would be one of the seven 20+ goal scorers with 24 and 48 points in40 games. The Flyers were still alive for the playoffs near the season’s end, but a bad loss to the Isles would end it. They would finish the season with a record of 30-39-11 for 71 points, dead last in the Patrick. However, the fourth place Islanders made the playoffs with a record of 31-38-11 for 73 points. Yes, the Flyers missed the playoffs by two points. And were eliminated by the team that did make it in.

For some teams, the response would be to say that is disappointing but look to re-tool and do better next season. The Flyers took this more seriously. After all, the Flyers did not just miss the playoffs; they missed it for the first time since 1972 and the third time ever. they finished last in the division, something they have never done until this season. This was enough to fire Bobby Clarke from the GM position. Again, this is a team that missed the playoffs by two points, did not get outscored by a large margin (goal difference was -7), and still had a team filled with fairly young players that several would become veterans.

While Jay Snider was the team president, Ed Snider was very much in charge. This era was before Comcast came in, so Snider was in control of the arena, the team, and other businesses like PRISM and WIP. At around this time, Snider would begin to attempt to lay the groundwork for The Spectrum II. Now known as the Wells Fargo Center. He wanted to keep the Flyers and 76ers in Philadelphia and with the Spectrum getting older, a new arena would do the trick. This would require a lot of negotiations with the 76ers owner and Philadelphia itself, but he would get it done. With his own money too. Keep that in the back of your mind for a couple of paragraphs.

Anyway, the Sniders decided to give the GM position to someone outside of the Flyers organization: Russ Farwell. He was the GM of the Seattle Thunderbirds in the WHL. It would be a different set of eyes for a franchise looking to get back to the postseason. His first main course of action: The NHL draft. The 1990 draft class would be an important one as the Flyers picked Mike Ricci at fourth overall, Chris Simon, Mikael Renberg, Chris Therien, Vyacheslav Butsayev, and Tommy Soderstrom among others. Farwell would sign Rod Dallman and Dale Kushner, formerly of the Islanders, and collegian Lance Pitlick. More importantly, he would lock up Hextall to a five-season deal and Tocchet to a four-season deal. Doug Sulliman would retire whilst John Stevens, Ken Linseman, and Ilkka Sinisalo signed elsewhere. In other words, it was mostly the same major players from last season and even the same coach. Maybe 1990-91 would go better.

It would not. The league average save percentage was 88.4%, which Hextall and Peeters beat but Wregget would not with an abysmal 86.7%. Hextall was hurt multiple times in this season so he only played in 36 games, requiring Wregget to play in 30 and Peeters in 26. Despite this, the Flyers still finished in the upper half of the league in terms of goals allowed. The offense actually took a step back. Even though Tocchet put up 40 goals and Eklund put up 50 assists, only Ricci (who made the team immediately) and Mellanby cracked 20 goals. Eklund, Craven, and Sutter came close, but not quite to 20. Kerr was once again beset by injuries so he could only play in 27 games to put up 10 goals and 14 assists. Holmgren had the team do well in the first two months of the season. But they went 4-8-3 in December and finished the season with a record of 6-15-4 in the final two months. The Flyers did improve by three points to finish with 76 points with a record of 33-37-10. They also missed the playoffs by three points to the Devils, who finished in fourth. For the first time in franchise history, the Flyers missed the playoffs twice in consecutive seasons. Not by much, but do not tell that to the team not used to this.

Farwell would make some significant moves in the 1991 offseason. First, Farwell was involved in a three-team trade with Edmonton and Los Angeles. First, the Flyers sent Scott Mellanby, Craig Fisher, and Craig Berube to Edmonton for Dave Brown, Cory Foster, and the signing rights to Jari Kurri. Then, the Flyers sent the rights to Kurri and Jeff Chychrunto Los Angeles for Steve Duchesne, Steve Kasper, and a fourth rounder in 1991. On the day that trade was made, the expansion draft for San Jose was held. Farwell unprotected several players including Peeters, Howe, and Kerr. The Sharks took Kerr, ending an 11-season run of 601 games, 363 goals, and 650 points as a Flyer. In the offseason, Peeters would be bought out by Farwell, Scott Sandelin would sign with Minnesota, and Farwell added Brad Jones and Al Conroy. Farwell would make a second significant trade in September ahead of the 1991-92 season. He sent Ron Sutter and Murray Baron to St. Louis for Rod Brind’Amour and Dan Quinn. A move for a younger scorer with a bright future. That would not be the only young player the Flyers would have coveted.

The 1991 NHL Draft had plenty of talent that would go on to have great careers in the NHL. The Flyers even drafted one of them at sixth overall: Peter Forsberg. They also drafted Dmitri Yushkevich among others. But all hype was on a bigger name: Eric Lindros. Standing at 6’4”, weighing at least 220, and making every scout drool with his amazing blend of speed, quickness, fluidity, power, and skill. He was an absolute stud for Oshawa in the OHL with a 71-goal, 149-point season in just 57 games. He was the CHL Player of the Year, the OHL MVP, and touted as the Player of the 1990s. A “power forward” that skated like a smaller skilled guy. Lindros was going to be the first overall pick in 1991 short of a crippling injury.

What he was not going to be was a Quebec Nordique. They held the pick and this was a period where they absolutely stunk. The story has changed a bit, but Lindros revealed in 2016 his main issue with Quebec was Marcel Aubut, owner of the team at the time. Quebec drafted him anyway, Lindros held out for the 1991-92 season as he played for the Canadian national team and Oshawa, and Aubut made it clear that Lindros would turn the franchise around and that he would not trade him. One of those statements was true.

Anyway, the 1991-92 season featured Farwell taking more of an active approach to the team. Brind’Amour turned out to be a great pick up as he led the team in goals, 33, and points, 77, for the season. Duchesne was a very productive defender with 56 points. Quinn even added 11 goals and 37 points in a more depth role. The team struggled early on, prompting a trade to bring in Kevin Dineen from Hartford in exchange for Craven (who had 6 points in 12 games) and a fourth rounder in 1992. Dineen would have a very good season for the Flyers with 26 goals and 56 points in 64 games. Those struggles continued into November and after some blowout losses, the 8-14-2 Flyers fired Holmgren and hired Bill Dineen to replace him. The team did respond well to Dineen at first and the Flyers became successful at home. Far less successful on the road. The 1992 portion of the season saw them go 15-4-2 in Philly and 5-16-1 away from it. Farwell kept making moves in the hope for something better. In January, Gord Murphy, Brian Dobbin, a third rounder in 1992 and a fourth rounder in 1993 were sent to Boston for Garry Galley, Wes Walz, and a third in 1993. Previous top scorer Tocchet was having an unlucky season with 13 goals and 29 points in 42 games. He also had the ‘C’ for this season. No longer. Farwell sent Tocchet, Kjell Samuelsson, Ken Wregget and a conditional third rounder in 1993 to Pittsburgh (!) for Mark Recchi, Brian Benning, and Los Angeles’ first rounder in 1992. A trade to the hated rivals? I’m still in shock of that one, but it did bring Recchi to Philly. Recchi made an instant impact with 10 goals and 27 points in 22 games. Still, even with all of these moves and the coaching change, the 1991-92 Flyers were one of the league’s poorer teams in terms of scoring goals. Giving up goals, not as bad even if it was 273 goals allowed. League average for save percentage that season was 88.6%; Hextall missed it with an 88.3% in 45 games, call-up Dominic Roussel beat it with a 90.8% in 17 games, and the traded Wregget missed it by a mile with an 86.5% in 23 games.

The result of all of this was a 32-37-11 record for 75 points and another last place finish in the Patrick Division. This time, the margin of missing the playoffs was substantial. They finished 12 points behind the Devils and Penguins for the final playoff spots in the division. Philadelphia has now missed the playoffs for three seasons and appear to be going backwards, not forwards.

Even though the reality was that the prior two seasons were missed by all of two wins, the perception from ownership was that the Flyers need to rebuild. That core from earlier in this section? All that remained was Hextall, Pelle Eklund (who had a rough 1991-92 season), and Mark Howe. A new group of younger players in Ricci, Brind’Amour, Recchi, and Duchesne was seemingly the way forward. But ownership did not want to stop there. There was another way to improve the team, and his name was Eric Lindros.

Kevin Kurz wrote this fantastic article going into depth about the history of the Lindros trade from the perspective of Jay Snider at The Athletic. If you have a subscription, then go read it. But it does confirm that ownership (Ed Snider) was concerned about the team even if they were not that far off from the postseason and even though the Spectrum was still filled with fans. A new arena was on its way and the team cannot be rebuilding for long. Lindros would someone to push the Flyers back to where they were in the 1970s and 1980s. And so Snider worked with Aubut to make a deal happen. Lindros was a hold out, but many teams were interested and so Quebec could leverage a massive return for this one prospect. The Flyers did not want to part with Rod Brind’Amour, reluctlantly included Forsberg and $15 million in cash (remember Snider had that arena thing he was funding and didn’t have Comcast involved), and were willing to include first round picks, Mike Ricci, Steve Duchense, and Ron Hextall. The final deal that Quebec accepted would be Ricci, Duchesne, Forsberg, Hextall, Kerry Huffman, Philly’s first in 1992, Philly’s first in 1993, and $15 million in cash. Farwell ensured that Lindros would play in Philadelphia; and Aubut committed to the deal verbally at the 1992 NHL Draft.

Except, no. Aubut went back to Snider a little later that day and tell him he agreed to a deal with the New York Rangers. A deal that included Tony Amonte, Alexei Kovalev, Sergei Nemchinov, James Patrick, a choice between Mike Richter or John Vanbiesbrouck, multiple picks, and $20 million in cash. Per Kurz’ article, while Ed Snider was away getting surgery, he urged Jay to contact Gil Stein and state that Quebec reneged on the deal. An arbitrator was hired to sort this out. Ten days, multiple witnesses, and hundreds of documents later, the arbitrator ruled that Quebec made the deal with Philadelphia first and while New York did nothing wrong, the trade with Philadelphia would go through. Since Philadelphia’s first rounder in 1992 was used by Philly due to the issues with the Lindros trade, it was agreed that Chris Simon and Philadelphia’s first round pick in 1994 would be sent to Quebec as well. Snider and Farwell got Lindros. Was it worth it? I will leave that up to you. But the feeling was that the Flyers were going to turn things around.

Not so far. The 1992-93 season did include Lindros playing in 61 games, putting up 41 goals and 75 points. Yes, a knee injury kept him to 61 games. But it was clear he was the real deal. (He also finished fourth in Calder voting because, goodness, Teemu Selanne dropped 76 goals that season). The Flyers offense was led by Recchi, who put up 53 goals and 70 assists to set a franchise record of 123 points; as well as Brind’Amour adding 37 goals and 86 points. Dineen even added 35 goals and 63 points. However, the scoring beyond those four and Brent Fedyk (acquired for a 1993 fourth rounder from Detroit) dwindled. The Flyers offense was around league median with 319 goals. The defensive side of things, well, it was not so good with 319 goals allowed. The league average save percentage was 88.3%. Without Ron Hextall, Soderstrom took over as the team’s top goalie and posted an 89.2%in 44 games. Roussel ended up as the 1B goalie with an 88.1% in 34 games, which was a touch below average. What sunk them was when Stephane Beauregard (acquired from Winnipeg for two picks) had to fill in for one of them. He posted a stinky 85.4% in 16 games, representing 59 goals against all by himself. While the Flyers went on a hot streak by the season’s end (8-1-0 in April), the team fell short of the playoffs again. The 1992-93 Flyers finished with a record of 36-37-11 for 83 points. They missed the playoffs by four points; the Devils and Islanders finished with 87 points each.

OK, so you’re Farwell. You were involved in one of the biggest trades in NHL history, nevermind franchise history. You moved out just about everyone who was crucial back in the late 1980s (Howe signed with Detroit in 1992). You have Recchi, Brind’Amour, and Lindros scoring tons while young. What do you do to get this team over 50% in points percentage and into the playoffs, which has been missed by fewer than 10 points in 3 of the last 4 seasons?

Farwell first made a coaching change. Bill Dineen was out and Terry Simpson was in. Ken Hitchcock would be hired as an assistant to Simpson. Second, some trades before the draft: Stephane Beauregard was sent back to Winnipeg for Philly’s third rounder in the 1993 draft and fifth rounder in 1994. The rights to Greg Johnson and a fifth in 1994 was sent to Detroit for Jim Cummins and a fourth in 1993. At the 1993 NHL Draft, the Flyers would pick Vaclav Prospal and Janne Niinimaa among others. New deals were given to Terry Carkner (who was traded in October to Detroit for Yves Racine and a fourth in 1994), Mark Recchi (six seasons!), and Tommy Soderstrom. Wes Walz was bought out, Ketih Acton signed elsewhere, and Simpson named Dineen captain with the intention of preparing Lindros for the role. Surely, this team that did not miss the playoffs by much would not miss it again by not very much, right?

Wrong. They would. For 1993-94, the Flyers’ offense was more productive with 294 goals scored. Recchi’s production dipped to “only” 40 goals and “only” 107 points to lead the team. Lindros missed a chunk of the season with another knee injury but still put up 44 goals and 97 points in 65 games. Brind’Amour was still a point machine with 97 points. Mikael Renberg debuted for the Flyers and put up a franchise record for rookies with 38 goals and 82 points in his first season. Racine added 52 points from the blueline, joining the 70 by Garry Galley. It was not all improvements and good times; Dineen fell to 19 goals and 42 points, Fedyk put up 20 goals but just 38 points; and Eklund put up only 17 points. Further, goaltending was more of an issue this season than the others in this drought. The league average save percentage was 89.3% that season. Roussel took over as the starter with an 89.6% in 60 games and Soderstrom was awful with an 86.4% (OOF) in 34 games. The Flyers defense conceded about a hundred shots more than the league average, yielding 314 goals allowed - the fourth most in the NHL. This was especially apparent as the team struggled to get results from December through March. Farwell as active in making moves, but nothing of real significance unless you think future considerations is significant (they’re not). The only one of real note to me was Pelle Eklund, the last piece of those late 1980 Flyer teams, a then-young guy thought to be part of the future, was sent to Dallas for an eighth round pick in 1994. The Flyers finished with a record of 35-39-10 for 80 points. They missed the playoffs for a fifth time. Once again, they missed it by four points as the Islanders made it.

Side note: The 1993-94 season was the first where the top 8 teams in the conference would make the playoffs. Even so, the 1993-94 Flyers would have made it if they finished fourth in the now-named Atlantic Division but they did not.

Now what do you do? Change leadership yet again. Farwell fired Simpson. Ed Snider fired Farwell. Snider convinced Bobby Clarke to come back to the Flyers and return to the GM position he was fired for earlier. I would think an apology was made, but who knows. It did cost the Flyers $500,000 and a second round pick as Clarke was with Florida at the time. No matter, Clarke would get right to work. He hired former Flyer Terry Murray as the head coach. He signed Craig MacTavish, Shjon Podein, and Shawn Anderson in free agency while re-signing Brent Fedyk and Galley. Clarke sent Racine to Montreal for Kevin Haller and traded Soderstrom to Long Island for Ron Hextall and a sixth round pick in 1995. And Lindros was made captain of the team. When the lockout ended and a 48-game season was set up, all eyes were on the team finally ending this playoff drought.

The 2-4-1 start undercut that goal. This caused Clarke to make a bold, but rewarding move. He traded Mark Recchi, the team’s top scorer of the past few seasons, to Montreal. Montreal sent back Eric Desjardins, Gilbert Dionne, and John LeClair. The return for Recchi was favorable. Desjardins would become a mainstay of the blueline in Philly. LeClair, though, would be a magical fit in Philly. LeClair was slotted alongside Lindros and Renberg. This line would become known as the “Legion of Doom” as all three forwards could and would score tons and make you, the opposition, pay the price. After that deal, the wins started piling up and the Flyers went on hot streaks in the second half of the season instead of mired in mediocre-or-worse results. Lindros was on another level all season long, tying Jaromir Jagr for the scoring lead of 70 points in the NHL. Lindros would win the Hart in 1995. Renberg put up 26 goals and 57 points; LeClair put up 25 goals and 49 points. And the depth was led by the still-dangerous Brind’Amour, Desjardins added 23 points in 34 games, Galley put up 22 points in 33 games before being traded for Petr Svoboda in April and others chipped in here and there like Fedyj, MacTavish, and Dineen. In a season where the league average save percentage was 89.8%, Hextall missed that mark with a 89% in 31 games but Roussel well surpassed it with a 91.4% in 19 games. The Flyers returned to being a top ten team in goals for and against. They finished the season with a record of 28-16-4 for 60 points. Philadelphia finished first in the Atlantic Division. They were not just back in the playoffs; they were back where they were in the 1980s. Job done. Mission complete. And all that.

Of course, the 1995 Flyers did go on a little run like their last playoff appearance. They beat Hasek’s Buffalo in five games. They swept the Rangers, which is always fun. In the Eastern Conference Finals, they battled New Jersey to a 2-2 series and it was 2-2 in Game 5. Until with 45 seconds left in regulation, Claude Lemieux embarrassed Hextall and Philly with this game winning goal. The Devils won that series in six. At least the Flyers could feel good about making the playoffs in every season from 1995 to 2006.

Any Other Thoughts: In retrospect, this drought bothers me. I get that the Sniders were not used to a team missing the playoffs and it was easier then to make the playoffs than not make it. Still, the Flyers went without the playoffs for five straight seasons and missed it by fewer than 10 points in all but one of them! This is not a team that needed to have a whole core changed or make a trade so massive to bring in Lindros. And while Lindros ended up being as talented as his hype suggested, even he did not bring the Flyers back to the promised land right away. The team even had league average goaltending in some of these lost seasons. This was a squad that just needed improvements and yet because ownership perceived things were worse than they were and they wanted big changes, it contributed to a franchise-long drought for a team that honestly was not that bad! I wonder how things would have went had Clarke not been dumped in 1990. Or if they made a bigger move to bring in a better goalie or, what they really needed, more depth in scoring. Still, this drought is a great example of how an owner’s or management’s perception can drive decisions that may end up not fixing an reasonably fixable situation.

The Pittsburgh Penguins

Playoff Misses and Proportion: 18 misses out of 54 total seasons; 33.3% missed.

Current Situation: The Pittsburgh Penguins’ core of future Hall of Famers may be getting older, but they remain as competitive as ever. The 2021-22 Penguins finished with a record of 46-25-11 for 103 points and another playoff appearance. Their only non-playoff season was in 2020 when they got upset in the Qualifying Round by Montreal. Before that, well, that is what will be covered for Pittsburgh.

A Summary of a Notable Drought: The team’s longest drought was in the 1980s, which took up part of Mario Lemieux’s first four years. The notable drought this post will cover is more recent and involves Mario Lemieux much more than you may remember. The drought ran for four seasons: 2001-02 to 2005-06. And this drought was driven by financial issues.

Remember that Ottawa was in dire straits and needed to be bought by Melnyk to secure their finances? The Penguins were in a similar situation in the 1990s. After a group led by Howard Baldwin and Roger Marino bought the Penguins from Ed DeBartolo Sr., it was apparent the group did not have the funds to keep up with the expenses of a hockey team. Especially a hockey team with several great players and performing well throughout the decade. Baldwin’s solution at the time was wage deferment. Mario Lemieux, among others, agreed to this. But when it was time to pay out the salaries, the owners did not have the money. The Penguins had to file for bankruptcy in 1998. (And fueled a feud between Baldwin and Marino) This only increased a concern that the team was going to go under or leave Pittsburgh. Lemieux, who retired in 1997, had an idea. Instead of requesting his deferred salary to be paid out - which was over $26 million, by the way - he offered to use what he was owed as part of a plan to buy the team. It would cover what he was owed, could make much more money, and could work to keep the Penguins in Pittsburgh and as a viable organization. Lemieux would need additional funding to do it, but he was a superstar and the Penguins were a good team. He could find someone. After some searching and being turned down by Mark Cuban (really), Ron Burkle entered the picture as did other investors, and Lemieux’s plan was taking shape. Lemieux and Burkle took over in 1999.

However, the situation was not all that secure for the Penguins. For one, there was matter of settling with all of the other creditors. For another, there was the matter of the bad business deals the team signed in the past. For a third, there was a matter of the Igloo. The Mellon Arena was one of the oldest arenas in the NHL at that time and a new venue would be needed to keep the Penguins viable in Pittsburgh. The latter would only keep the rumors going about the team moving out of Pittsburgh. The first part, though, did mean the Penguins did need to operate under a tight budget. This meant salaries had to be cut.

The 1999-2000 Penguins were still a quality team. Jaromir Jagr was still a scoring force and led the team with 42 goals and 96 points. There was a group of talented forwards to add to the attack: Kovalev, Robert Lang, Martin Straka, Jan Hrdina, and German Titov. Defense was a bit iffy and J-S Aubin was the top goaltender, taking over an aging Tom Barrasso. Due to the need to cut salary, Barrasso was traded to Ottawa for Ron Tugnutt and Janne Laukkanen; Titov was sent to Edmonton for Josef Beranek; and early in the season Kevin Hatcher was flipped to New York for Peter Popovic. Kevin Constantine was fired for a poor start, Herb Brooks was brought in to salvage the season, the season was salvaged with 88 points, a playoff appearance, and a second round exit.

The 2000-01 season would be the last hurrah before a playoff drought with the concerns of financial and relocation concerns. Brooks stepped down to be a scout, Ivan Hlinka was named as the head coach. Mario Lemieux returned to the ice in 2000 to help out the team he owned, and he still had plenty in the tank with 35 goals and 76 points in 43 games. He added plenty to a team already enjoying Jagr dropping 52 goals and 121 points, Kovalev and Straka putting up 95 points, and Lang putting up 80 points. Aubin struggled in net, an acquired Garth Snow was not much better, but call up Johan Hedberg did well in a short-stint and “Moose” earned playoff games as the Penguins went all the way to the Eastern Conference Finals. Only to be defeated by the Devils in a glorious five games. While they still gave up a lot of goals (256 was fifth worst in the NHL), they outscored their problems.

They could not outscore the financial issues where salaries needed to be cut. And so GM Craig Patrick had to do the seemingly unthinkable: trade Jaromir Jagr. Remember that Jagr was putting up 100+ point seasons regularly for Pittsburgh. He put up over 1,000 points with the Penguins alone. But the Penguins were unsure they could pay Jagr, plus who knows how much he had to defer his salary. Patrick had to find the right deal. Instead, Patrick proceeded to make one of the worst trades possible. Jagr (and Frantisek Kucera) was traded to Washington for Kris Beech, Michal Sivek, and Ross Lupaschuk. While those were thought to be good prospects at the time, neither of them would pan out at the NHL level. Jagr proceeded to sign an $88 million over eight-season contract with Washington. Patrick was given the OK to re-sign much of the other Penguins in the hopes of maintaining the core for the next season and be competitive.

They were not competitive. Without Jagr, the team lost a lot of its offensive punch. Opposing players could target the other forwards without having to worry about Jagr torching them. Injuries were rife; Lemieux was kept to 24 games, Kovalev led the team with 76 points but only in 67 games; Lang got into 62 games; and Straka only got to play 13 games in 2001-02. Hrdina and Aleksey Morozov had fine seasons for what they were. But the team got to see first hand that Beech was not that good, Milan Kraft from the system was not that good, and a full season of Johan Hedberg was not that good (90.4% save percentage in 66 games) with Aubin backing him up being far worse (87.9% save percentage). The defense took a hit as Darius Kasparitis - the ATOI leader on defense that season - was dealt away to Colorado by the deadline for Rick Berryt and Ville Nieminen. This meant more big minutes for Michal Rozsival and Ian Moran - which was bad in general. Hlinka was fired four games into the season and replaced by Rick Kehoe. The Penguins went from a 96-point season to a 69-point season in 2001-02.

After a 2002 Draft Class led by Ryan Whitney which included Maxime Talbot, mostly the same team returned for 2002-03 under Kehoe. The team’s offense and defense was mostly the same; they did not have enough of either. While Lemieux was healthier to play in 67 games and put up 91 points, the rest of the team sagged. One of the few bright spots was waiver pick-up Dick Tarnstrom, who led the defense in average ice time and points with 46 in 60 games. Still, the depth of the squad was gashed as players got opportunities that maybe they were not ready for but had to play anyway. Morozov was only able to play in 27 games (did put up 25 points). Straka got to play 60 games as a plus for 46 points. Hedberg only played in 41 games and posted a poor 89.5% save percentage; Sebastien Caron and Aubin backfilled the other games with Caron being the better with a 91.6% save percentage. But the team still bled goals. And talent. In February, GM Patrick traded Alexei Kovalev, one of Pittsburgh’s top scorers (not just in those days, but also 64 points in 57 games in 2002-03), back to New York. The deal was Kovalev, Dan LaCouture, Janne Laukkanen, and Michael Wilson for Rico Fata, Richard Lintner, Mikael Samuelsson, and Joel Bouchard. In March, the Patrick traded a productive Jan Hrdina with Francois Leroux for Ramzi Abid, Dan Focht, and Guillaume Lefebvre. Not that they were impactful but depth players like Randy Robitaille, Marc Bergevin, Shean Donovan, Ian Moran, and Wayne Primeau were all traded too. The team was younger, weaker in quality, and finished hard into last in the Atlantic and second last in the East with a 27-44-6-5 record for 65 points.

Kehoe resigned after the 2002-03 season and Patrick made the choice to bring Eddie Olczyk from the broadcast booth to the bench. Yes, Eddie O became the new head coach. Patrick oversaw an offseason of even further losses. At the 2003 NHL Draft, he would swap first rounders, take Florida’s third for their second, and send Samuelsson to Florida to move up to first overall. They took goalie Marc-Andre Fleury as Florida was ensured they could take Nathan Horton. The rest of the draft class is interesting if unimpressive with Ryan Stone, disgrace Dan Carcillo, Paul Bissonnette, and Matt Moulson. The team saw Bouchard, Nieminen, and Lintner sign elsewhere. Free agent signings were slim and included the likes of Kelly Buchberger, Martin Brochu, and Drake Berehowsky. Patrick’s real big move of the offseason was to trade Johan Hedberg to Vancouver for a second round pick. That and some entry level deals to Ryan Malone, Fleury, Whitney, and Talbot.

The 2003-04 season would be the worst season in Penguins history since the early 1980s. The Penguins were absolutely torched on defense. The league average amount of shots allowed was 2,300; the Penguins allowed 2,720. The average penalty kill success rate was 83.54%, the Penguins’ success rate was 77.24%. The team allowed 303 goals, the most in the NHL as Caron (40 GP, 88.3 Sv%), Aubin (22 GP, 90.8 Sv%), Fleury (21 GP, 89.6 Sv%), and Andy Chiodo (8 GP, 89.2 Sv%) combined for 290 goals allowed. Add in 13 empty netters and the 2003-04 Penguins let up 303 goals all season. Lemieux was injured for most of the season as he only played in 10 games. The team’s leading scorer was Tarnstrom with 52 points. Only Ryan Malone broke 20 goals; he put up 22 and 43 points in his first full season. The team combined for 190 goals. The team was loaded with veterans happy to have a job and young players not ready yet or never-will-be-ready for the NHL. It was dreadful hockey. Another name player was traded away; Martin Straka was sent to Los Angeles for Martin Strbak and Sergei Anshakov. The only positive trade the team made all season was moving Berehowsky to Toronto for Ric Jackman, who at least put up 24 points in 25 games for Pittsburgh. The team was so bad, they had an 18-game winless streak amid a 23-47-8-4 record for 58 points. They had the lowest point total in the NHL. Surely, it could not get any worse.

One of the issues of the lockout of 2004-05 was how the league would handle financially insolvent teams like Pittsburgh and Ottawa. While Melnyk took care of Ottawa, the Penguins were far from secure in Pittsburgh. The salary cap and revenue sharing that eventually won out from that lockout would help teams like Pittsburgh out tremendously. They were not done yet. Remember that arena issue? Despite the stardom of Lemieux, both Pittsburgh and Pennsylvania were not terribly interested in helping the Penguins with getting a new arena. That they became a pitiful hockey team did not help at all. This would lead to problems that would not get resolved until 2007. At least the team did not have to play on the cheap for much longer.

And they would not need to given the incoming prospects. The 2004 NHL Draft would yield players like Evgeni Malkin, Alex Goligoski, and Tyler Kennedy. Malkin alone was a player a team could build around. They would get a better gift after the 2004-05 lockout: a lottery win. Without a 2004-05 season, a lottery was used to determine the first overall pick in the NHL Draft. The prize: Sidney Crosby, someone touted to be the next special hockey player. The winner: Pittsburgh. And the 2005 NHL Draft was more than just Crosby at first overall. Kris Letang was found at 62nd overall. With Crosby coming in, interest re-ignited for the Penguins. The team could not hold back; they had to take advantage of this youth movement coming in.

And so Patrick got to work. Ahead of time, Mark Recchi was signed in 2004 and the team saw Morozov, Aubin, and Kraft among many sign elsewhere. To support Fleury in net, Patrick sent a fourth rounder in 2006 to Chicago for Jocelyn Thibault. Beech was not doing much, so he was moved to Nashville for a conditional pick. Thanks to the cap, Patrick signed Sergei Gonchar, Ziggy Palffy, John LeClair, and Andre Roy to multi-year deals. Malkin could not come over from Russia (yet), but the Crosby show was ready for 2005-06.

What was not ready for 2005-06 was a competent defense or even strong goaltending. The Penguins goalies combined for a team save percentage of 88.8% - in a league where 89.9% was the league average. The Penguins still allowed close to 300 more shots than the average NHL team, leading to the team allowing a league-worst 310 goals. Gonchar and Whitney were productive and Brooks Orpik was working his way up the depth chart, but the defensive stylings needed to get tighter. While productive, Tarnstrom and Jackman were not longterm answers on the blueline and they were dealt by the 2006 trade deadline. The coaching certainly did not help. Olczyk was fired after an 8-17-6 start and replaced by Michel Therrien. He improved things a bit but he alone could not salvage the season. A season that also saw the real end of Lemieux as a player. While productive with 22 points in 26 games, he struggled with the speed of the NHL and was diagnosed with an irregular heartbeat. Mario hung up the jersey for good on January 24, 2006. But the Crosby show was everything one hoped it would be. As a rookie, he scored 39 goals and put up 102 points, franchise records for Penguins rookies. He was only second to Ovechkin for the Calder but clearly showed he was the one to carry Pittsburgh forward. It was also clear the team’s depth in scoring needed help. Gonchar finished second on the team in scoring with 58. While Recchi, Palffy, and LeClair chipped in, the future was not in those guys. A new direction was needed - and Lemieux the owner knew that.

This also meant a new GM was needed. After the 22-46-14 record for 58 points, Patrick was let go by the Penguins. Assistant GM Ray Shero would take over as the team’s new GM. A new staff would follow with Chuck Fletcher becoming his assistant and a new goalie coach in Gilles Meloche. Meanwhile the arena issue loomed large, leading to more worries about relocation. Research in Motion CEO Jim Balsillie was thought to buy the team but pulled out a week later. Efforts to get a new arena in line with Isle of Capri Casinos big failed; spurring hopes in Kansas City which had an arena ready to go - and it was known Pittsburgh can move after 2006-07. Since the Capri deal fell through, Lemieux openly stated that they were meeting with officials in Kansas City and had interest from Houston, Winnipeg, Portland, and Oklahoma City. This would be a gut punch for the Penguin fans. The team gets the best young player the team has had since Jagr - and the hero of the franchise may end up moving them out of Pittsburgh.

While this was ongoing, the 2006-07 season still needed to be played. Shero would bring back Mark Recchi for another year, sign Mark Eaton to help the D a bit, get Evgeni Malkin signed, extend Fleury, give ELCs to Letang and 2006 first round pick Jordan Staal, and keep Malone along. How would season 2 of Crosby go?

Somehow, better than the first. The Penguins made improvements over nearly every aspect of last season and this whole drought. The goaltending was above league average. In a season where the NHL’s average was 90.3%, Fleury beat that with a 90.6% in 67 games and Thibault beat it with a 90.9% in 22 games. The Penguins defense only gave up about a hundred more shots than the league average, which helped the Penguins finish at the league median for goals allowed. The offense took a big step forward with the addition of Malkin, who put up 33 goals and 85 points in his NHL debut. Staal’s rookie season yielded an outstanding 29 goals and 48 2 points. There was plenty of depth in scoring: Recchi put up 24 goals and 68 points; Michel Ouellet put up 19 goals and 48 points; and Colby Armstrong, Erik Christensen, Maxime Talbot, and Malone each put up at least double digits goal. But Crosby elevated everything. He put up 36 goals and 120 points - a career high to this day - to lead the team in scoring. Crosby was named to the NHL All Star first team, won the Art Ross, the Lester Pearson, and the Hart Memorial Trophy. All the while, Shero had a chance to do something Patrick could not do in his final seasons: add to the roster. They were not major ones - Gary Roberts and Georges Laraque - but additions all the same. The Penguins went from a 58-point season to finish 2006-07 with 105 points, a record of 47-24-11. Yes, an improvement of 37 points. They were back in the playoffs. They lost quickly, but it would be a lasting moment as the Penguins have made the playoffs in every season since - until they got knocked out of the Qualifying Round by Montreal in 2020.

The Penguins would also last in Pittsburgh. On March 13, 2007, the government entities of Pennsylvania would agree to a deal to fund a new arena for the Penguins. It would be built for the 2009-10 season. The arena came with a new lease requirement to keep the Penguins in Pittsburgh for 30 years. The final question mark that came with Mario Lemieux taking over has been answered and in the way he wanted it. Lemieux remains as the legendary hero of the Penguins, from his time as a player and now as an owner that did bring the team back from the brink. The four season “dark period” led to a far brighter future - and three more Stanley Cups.

Any Other Thoughts: The Penguins certainly rebuilt themselves in the “traditional” sense. They were bad. They drafted young players that would be important to the team. Those young players developed - some quicker than others - to make the team better. Granted, being able to draft Whitney, Fleury, Malkin, Crosby, and Staal in five straight first rounds is not something everyone can just do or even plan to do. The 2005-06 season underscores the point that having an unusually great player alone is not enough; a competitive NHL team needs quality in depth, coaching, goaltending, and other areas. It was not until all of those prospects joined and the defense improved and the goaltending was improved and the coaching was improved and one of those young players was the MVP and leading scorer of the whole league that the Penguins improved by 37 points in a single season.

The whole drought is underscored by the issues with ownership. Imagine if the Penguins did not go bankrupt to begin with. Imagine if ownership, in a way to cut salaries, also removed Patrick earlier and brought in someone with few ties to the organization to make those decisions to rebuild. Imagine if the arena issue was sorted out earlier. This whole four-season drought and rebuild was a result of the previous owners being so poor (literally) and Lemieux, Burkle, and the other investors having to clean up their mess and figure out getting a new arena. If nothing else, understand that bad ownership can really cause problems for a hockey team that management, coaches, and players may not be able to overcome.

The San Jose Sharks

Playoff Misses and Proportion: 9 misses out of 30 total seasons; 30% missed.

Current Situation: The San Jose Sharks have not had a playoff drought of more than two seasons - until now. They ended 2021-22 with their third straight season without the playoffs. The Sharks finished last season with a record of 32-37-13 for 77 points, their best of the last three seasons. Now with a new GM in former Shark player Mike Grier, the team looks to right the ship before this drought goes on for too long.

A Summary of a Notable Drought: I have to use the current one here because the other droughts make little sense. The 1991-92 and 1992-93 Sharks were just hideously terrible. The 1992-93 Sharks had 11 wins. 11! They somehow scraped by sub-mediocrity to get into the postseason for two seasons after that. It was possible to do so then given how the playoff and divisions were structured in the 1990s. After that, they cratered for two more seasons, went back to scraping their way in, and then emerged as a consistently good to great team with just two playoff misses before this current drought. To fully appreciate their current situation, we need to go back to two seasons before their ongoing drought:

The 2017-18 season was like many others under GM Ron Wilson. A good, even a very good, regular season team and they fell short in the playoffs. Going into that season, Wilson handed out two massive contract extensions: a six-season, $34.5 million deal to goalie Martin Jones and an eight-season, $56 million extension for defenseman Marc-Edouard Vlasic. Unlike Ottawa and Pittsburgh, San Jose was willing to spend. They even brought back Joe Thornton for a season at $8 million. All seemed good for the Sharks in the season. Brent Burns shot the puck a lot and just edged captain Joe Pavelski for the team lead in points. Logan Couture put up 34 goals and 61 points. Some youth was present in Tomas Hertl, Chris Tierney, Kevin Labanc, and the first full season of Timo Meier. Jones and Aaron Dell posted save percentages above 91%. Wilson added a big forward during the season: he traded Danny O’Regan, a conditional first rounder in 2019, and a conditional fourth rounder in 2020 for Evander Kane. Would this be the Sharks year? No. The Peter DeBoer coached team fell in the second round to Las Vegas, who went all the way to the Finals in their first season. Clearly, more was needed to get the Sharks to the championship series. The Sharks ended 2017-18 with a cap hit of $71.5 million.

The Sharks’ path changed dramatically thanks to the Ottawa Senators. In June 2019, Ottawa chose to get rid of Mike Hoffman. The Sharks used this opportunity in a three-season trade to move Mikkel Boedker’s deal and pick up some extra picks from Florida. Paul Martin was bought out by Wilson to free up some more space. This allowed Wilson to give Logan Couture an eight-season contract extension worth $64 million; lock up Kane on a seven-season contract worth $49 million; Tomas Hertl a four-season contract extension worth $22.5 million; and bring back Thornton for $5 million. Dylan DeMelo got a minor bump in pay on a $1.8 million deal over two seasons. Chris Tierney and the Sharks went to arbitration and the ruling was a two-season and $5.875 million deal. In the background, Ottawa’s ace defenseman Erik Karlsson was becoming available. Ottawa was willing to hear offers. You want to go over the top? Opponents loathed Brent Burns being a two-way threat; imagine if they had to deal with Karlsson as well. Karlsson can put them over the top.

On September 13, Wilson pulled the trigger. Karlsson had a cap hit of $6.5 million and a season left on his contract. To help make the money work, Tierney, DeMelo, and Rudolf Balcers on an ELC were in the package to make it easier to take on that hit. Prospect Josh Norris was included in the package along with a second rounder in 2019 and a first in 2020. Wilson now had a blueline that could be led by Karlsson or Burns along with Vlasic and Justin Braun in support. The Sharks were looking good.

The 2018-19 season did look good on the surface for the Sharks. Another strong 5-on-5 season. Another 100+ point record at 46-27-9. Burns put up 67 assists and 83 points. Hertl put up 35 goals and 74 points. Couture put up 70 points. Meier broke out for 30 goals and 66 points. Pavelski put up 38 goals. A full season of Kane yielded 30 goals and 56 points. Wilson moved two picks to Detroit to add Gustav Nyquist for what would be another playoff run. However, Karlsson suffered from injury and played only 53 games. Put up 45 points, but only 53 games. The goaltending tandem of Jones and Dell combined for a save percentage of 89.4%. No matter: Karlsson would be back for the playoffs and the Sharks did go on a run to the Western Conference Finals. They prevailed over Las Vegas in 7 and beat Colorado in 7. Couture and Hertl were especially good with 14 and 10 goals, respectively. But they fell to the eventual champs in St. Louis. Slightly different verse, same song, right? (By the way, the Sharks’ final cap hit for 2018-19 was $79.12 million)

Well, no. Unfortunately, the music would change and it would not get better for the Sharks. After the playoffs, Wilson made another massive decision. Karlsson was a pending UFA. While he missed a chunk of the season, he did demonstrate his dynamic abilities for the Sharks and how he can be a consistent threat. He just turned 29 and wanted a lucrative, long term deal. San Jose was convinced. And so they signed Karlsson to an eight season, $92 million contract. Yes, $92 million. Yes, a cap hit of $11.5 million - far surpassing the big hits from Couture’s, Hertl’s, Jones’ and Vlasic’s extensions as well as Kane’s contract.

This meant space had to be made. The next day, Braun was sent to Philadelphia for two picks. After a lot of pick trading at the 2019 NHL Draft, free agency ensued. Nyquist signed with Columbus; Joonas Donskoi signed with Colorado; and captain Joe Pavelski signed with Dallas. The Pavelski departure was big; more than just the team’s captain, he was a consistent scorer for the Sharks even after entering his 30s. Wilson was more focused on internal moves: a four-season contract worth $24 million for Timo Meier, a one-season deal with Kevin Labanc for a $1 million, another one-season deal for Joe Thornton at $2 million, and another throwback: Patrick Marleau for a season. As much as Pavelski would be missed, surely, things would go well again for the Sharks? The core of new-captain Couture, Meier, Hertl, Karlsson, Burns, and Vlasic were still there.

Nope. The 2019-20 season started off terrible with a four-game losing streak in an October where they went 4-8-1. While they rebounded in November, a 2-9-2 December would put the Sharks in a deep hole. It would also cost DeBoer his job; Bob Boughner took over on an interim basis. Jones put up another sub-90% save percentage and Dell put up a 90.7% - not enough to stem the Sharks from being among allowing the most goals. While the season was shortened due to the pandemic, no Shark skater topped 50 points. Meier led the team with 49 and was one of two players who scored over 20 goals each. The other was Evander Kane, who was being sued by a casino during the season. Karlsson, Couture, and Hertl missed at least some time due to injury. That limited their contributions as well. For the first time in a long time, Wilson had to be a seller by the deadline. Brenden Dillon (with retained salary!) was sent to Washington; Marleau was sent to Pittsburgh, and Barclay Goodrow and a third garnered a first rounder from Tampa Bay. When the season was ended, the Sharks had a record of 29-36-5 for 63 points. They finished dead last in the Pacific Division and did not make the Return to Play tournament. Oh, and their final cap hit was $81.1 million. The Sharks were well short of both cap space and an expanded playoff tournament.

Wilson knew further changes needed to be made. Goaltending was an issue as Jones was bad in recent seasons. Therefore, he acquired Devan Dubnyk for a fifth rounder from Minnesota. Cheap depth was needed so Ryan Donato was acquired. Ahead of the 56-game season in 2021, Wilson brought back Matt Nieto for a season, saw Dell and Thornton sign with Toronto, and give out a four-season contract to Labanc worth $18.9 million. Wilson clearly believed in this core of Meier, Couture, Hertl, Kane, Karlsson, Burns, Vlasic, and now Labanc given the big contracts he gave them. At least he knew Jones-Dell was not a good tandem and Dubnyk could theoretically push Jones to be better.

Theory did not come out in reality. Both Jones and Dubnyk posted total save percentages less than 90%. Not helping matters was that the Boughner-led Sharks fell below 50% in both CF% and xGF% in 5-on-5 compared to the DeBoer seasons. This led to the Sharks finishing 29th in goals allowed in the NHL. The offense could not out-score that. Only Kane managed to break 20 goals in the 56-game season with 22 goals and 49 points. Kane was beginning to have issues in the locker room, as well as more serious financial issues as he declared bankruptcy in January. While on a $49 million contract. Regardless, Karlsson at least played most of the season; but his production dropped to 22 points in 52 games. Burns, now in his age 35 season, put up just 29 points in 56 games. Hertl, Couture, and Meier fared better in terms of production but they could not lift the team beyond 150 goals scored (they scored 146). The Sharks finished sixth in the West with a record of 21-28-7 for 49 points. It was just the second playoff miss in as many years.

Worse, the team was still near the cap ceiling. The 2021 Sharks’ final cap hit was $79.9 million. Wilson did not do much selling by the trade deadline except for moving Dubnyk for Greg Patyrn - which is not much of anything. The big deals of Karlsson, Burns, Couture, Vlasic, Kane, Meier, Jones, and Hertl were still on the books. If they did not perform excellently, then the team was in a position to suffer. And given the length remaining on most of these deals, few team were interested in “helping” San Jose with their issues.

Wilson went into the 2021 offseason with the intention of, well, fixing something here. He did recognize that Jones was not performing like a goalie should on a $5.75 million cap hit. The Sharks bought him out. To replace him, James Reimer was signed for a two-season deal worth $4.5 million. Adin Hill was picked up from Arizona for a seventh rounder as depth. Recognizing the depth scoring beyond the core was, well, weak; Wilson found the room to bring in Nick Bonino and Andrew Cogliano to try to help. Wilson also found the room to somehow hand out another massive contract extension. Hertl was signed to an eight-season extension worth $65.1 million - which starts in this coming season. That’s an $8.1375 million cap hit on top of all of the others on the team. Something to cause headaches for the future.

In the time of the 2021 offseason, there was already a headache. Evander Kane. Kane’s issues mounted before the 2021-22 season. He was accused of betting on games by his estranged wife (this was not substantiated), he was accused of domestic violence after a restraining order was filed (also not substantiated), and he was investigated for violating COVID-19 protocols with a fake vaccine card. The last one was subtantiated and Kane was suspended for 21 games. Kane was also not popular in the locker room and were not unhappy he was suspended. The Kane saga would continue into the 2021-22 season itself.

Wilson would not be present for much of it. He had to take a medical leave of absence in late November. He officially stepped down after 19 seasons of being San Jose’s GM. Assistant GM Joe Will had to take care of the team’s business while Wilson was away. This meant dealing with Kane upon his return. The decision: put him on waivers to be demoted to the Barracuda as not upset the locker room. 21 games into the season, the Sharks were 11-9-1 - not great but not bad either. There was reason to not add any discord back into the team. After five games in the AHL, he tested positive for COVID-19, entered the AHL’s protocol, and managed to violate that at well. That was the last straw. On January 8, they terminated his contract. Kane would go on to sign a contract with Edmonton.

While Kane did not return to upset the locker room, the season would go off the rails. After a 5-5-0 December, the team slumped in the 2022 portion of the season. The good news was that the goaltending was legitimately better. Reimer posted a 91.1% in 48 games, Hill put up a 90.6% in 25 games, and Will acquired Kaapo Kahkonen by the deadline - he posted a 91.6% in 11 games. Injuries did undercut the net, leading to Zach Sawchenko getting seven appearances and Alex Stalock brought in for future considerations for a game. Still, the Sharks allowed a more respectable 261 goals against for 21st in the NHL. The offense was still lacking. The Sharks scored just 211 goals, 30th most in the NHL. While Meier and Hertl each put up 35 and 30 goals, Couture only scored 23, and only another six players broke 10 goals. Nieto did not. Cogliano did not - and Will shipped him out at the deadline. Bonino did with 16 goals but just 26 points. Injuries limited Karlsson to 50 games and 35 points. Burns, in his age 36 season, was still packing on the minutes and did put up up points - but it was clear he was not the same player from even just two seasons ago. As a whole, Boughner’s squad was wrecked in 5-on-5 - which just made the whole process worse. Record-wise, the Sharks did not finish last in the division but still put up a disappointing 32-37-13 record for 77 points. They missed the playoffs by 20 points. With Kane’s deal terminated and Jones’ buyout, the Sharks finished the season with a cap hit of $76.5 million. Still not a lot of space to work with - especially with Hertl’s extension about to kick in.

With Wilson stepped down, the Sharks sought out a new GM to presumably lead to some kind of rebuild after three seasons without the playoffs. Ownership decided on former Shark (and Oiler and Capital and Sabre) player and former Devils assistant coach, Mike Grier. He was named on July 5, just before 2022 NHL Draft and free agency. Grier did get right to work on getting the Sharks out of some of their long-standing, big-money contracts. Or at least one of them. On July 13, Grier traded Brent Burns (with 34% retained salary) and Lane Pederson to Carolina for Steven Lorentz, Eeru Makiniemi, and a conditional third round pick. Burns was great as a Shark but he was not getting any younger to justify a $8 million cap hit. The retained salary means $2.72 million will be on the books until 2025, joining the dead cap hit from Jones’ buyout that lasts until 2027.

He also traded John Leonard and a third rounder for Luke Kunin, whom he signed to a two-season deal. Free agency featured defenseman Matt Benning signed to a four-season deal, center Nico Sturm for three seasons, a return of Aaron Dell as depth, and new deals for Kakhonen and Mario Ferraro. More will have to be done. As of this writing, CapFriendly has the Sharks at $83.7 million - which is $1.2 million over the cap. Perhaps Labanc is moved to LTIR to wipe that away. Perhaps some moves to the Barracuda would add some more space. But Grier’s mission will be to make hard decisions to set the Sharks up for the future. Timo Meier’s deal ends after this season, another goalie will be needed as Reimer and Hill are UFAs after 2023, and the team is stuck with Hertl’s extension, Karlsson and Vlasic on big contracts with NMCs, and captain Couture on a big deal with a modified-no trade clause. While replacing Boughner with Dan Quinn may help the 5-on-5 play on the ice (Boughner’s last season was awful at it so even Dan Quinn may help it), the drought may continue as Grier sorts out the situations Wilson made as he locked in his core just before and amid this ongoing drought.

Any Other Thoughts: One of the complaints I have seen from the People Who Matter since the rebuild started with Ray Shero was about the Devils not spending a lot of money. The Sharks are a current example of why a team should not spend close to or up to the cap ceiling when they are not good. While the players Wilson signed were good and their agents commanded value, the Sharks are fairly inflexible when it comes to making improvements or even tearing down the roster. They are not impossible to move, but it will be difficult to get out from, say, the Vlasic contract - which still has four more seasons at a $7 million cap hit for the 35-year old defensive defenseman. This will prevent the team from bringing up prospects or other free agents in the hopes of finding a player to develop for the future at any position. Goaltending did improve in 2021-22, but it needs to be secured; and the forwards do need depth. Deals like Vlasic, Karlsson, Hertl’s extension, and Couture make that harder - which makes Grier’s position unenviable. If ownership and management knows the team is not going to be good, then it is in their best interest to have space in order to go in a different direction quickly and efficiently if initial plans do not work. This is a lesson that Detroit has recently learned the hard way. I hope it is not a lesson the Devils will learn as they have committed to their core without making the other improvements to take them where they want to go.

The St. Louis Blues

Playoff Misses and Proportion: 9 misses out of 54 total seasons; 16.7% missed.

Current Situation: Since their last playoff miss in 2017-18, the Blues have made it to the post-season four straight times: They sang Gloria in 2019, got early exits in the next two years, and put up a 49-22-11 record for 109 points and lost in the second round to the eventual Cup champions. At least they were the only team in the West to actually beat the Avs in the postseason this year.

A Summary of a Notable Drought: Like Colorado, Pre-Pegula Buffalo, Dallas with one exception, and Boston after 1968, St. Louis just has not done long playoff droughts. They hit the ground running in 1967-68. You can use both of your hands to count the seasons where they did not qualify for the postseason. This is even more impressive given the team’s ownership issues in the 1980s led to the team nearly moving to Saskatoon, Saskatchewan in 1983s. This makes their three-season spell outside of the second season from 2005-06 to 2007-08 more interesting.

It was the beginning of the cap era and, clearly, a new one for the Blues. Before the 2004-05 lockout, the Blues were a consistent playoff team. They made it in every season since the 1979-80 season. The 2003-04 Blues did it like any other. Sure, it was not without some issues. Joel Quenneville was fired mid-season and Mike Kitchen took over. The team finished with just 91 points, which was still good enough to qualify in that season. The team was also old. Then 31-year old Chris Osgood had a good season as a starting goaltender. The top six scorers were all 29 or older: Keith Tkachuk (31, 33 goals, 71 points), Doug Weight (33, 65 points), Pavol Demitra (29, 23 goals and 58 points), Chris Pronger (29, 54 points), Dallas Drake, and Scott Mellanby (37, 31 points). The team also included Alexander Khavanov, Mike Sillinger (added at the deadline), Murray Baron, and cameos from Scott Pellerin and Al MacInnis. They did have a 22-year old Barret Jackman, although he missed most of his second NHL season due to injury with 15 games played. And veteran Petr Cajanek was drafted in 2001, he was on the roster. The Blues would go to the playoffs and get eliminated in 5 games to San Jose.

What did the system have for this aging team? From their drafts, they had Jay McClement, their 2002 draft class (basically a bust), Shawn Belle, David Backes, and Lee Stempniak. The 2004 NHL Draft would see St. Louis pick Carl Soderberg, Nikita Nikitin, and Roman Polak. Oh, and goalie Marek Schwarz with their first rounder. Those players would play in the NHL and some for quite a while - but the prospect pool was not filled with prospects between later picks and not picking particularly well (Jeff Taffe and Shawn Belle did not work out, nor did anyone in that 2002 class). The 2005 NHL Draft class would help that a lot as T.J. Oshie, Ben Bishop, and Ryan Reeves were selected.

Prior to the lockout, the Blues lost plenty of veterans. Brian Savage was waived. Mellanby signed with Atlanta. Osgood, MacInnis, Pellerin, and Baron all saw their contracts expire. The biggest loss was Demitra, who signed with Dukla Trencin in Slovakia ahead of the lockout - and he would not return to the Blues when the NHL restarted in 2005-06. GM Larry Pleau did not add much other than signing Dennis Wideman out of juniors, trading Belle for goalie Jason Bacashihua, and sending a conditional fourth rounder to Ottawa for Patrick Lalime. Pleau clearly felt goaltending was going to be an issue with Osgood walking.

When the salary cap was put into place, the Blues had their own issues with ownership - again. Back in 1999, Nancy Walton-Laurie and Bill Laurie bought the team. In June 2005, the Lauries announced they would sell the team. This meant that GM Larry Pleau was encouraged to not add salary and perhaps even remove some. This was a factor in the decision to trade Chris Pronger to Edmonton, who had cap space to sign him, for Eric Brewer, Jeff Woywitka, and Doug Lynch. This also explained why Pleau’s biggest free agent signings were former Albany River Rat Dean McAmmond and former Memphis RiverKing Scott Young. It would also be a factor in some other moves made during the 2005-06 season.

That season would be real bad one for the Blues. Their worst since the late 1970s, in fact. Keith Tkachuk failed his physical before the season and suffered injuries, limiting him to 41 games. Weight and Sillinger would be traded in January. Sillinger was sent to Nashville for Timofei Shishkanov. Weight would be sent to Carolina for Jesse Boulerice, Michael Zigomanius, the rights to Magnus Khanberg, Carolina’s first round pick in 2006, and a pair of fourth rounders. Even though Weight was traded, his 44 points in 47 games still put him second on the team in scoring. The 38 year old Scott Young, formerly of the Central Hockey League, led the team in points with 49 points and second in goals with 18, only behind Sillinger’s 22. McAmmond finished fifth on the team in scoring. With Pronger gone, the defense was carried by Christian Backman, Brewer, Wideman, and 39-year old Eric Weinrich - who was traded to Vancouver in March for Tomas Mojzis and a third in 2006. The goaltending was split between Lalime being bad for 31 games (88.1 Sv%!), Bacashihua not doing well for 19 games (89.9 Sv%), Reinhard Divis being far worse for 12 games (84 Sv%!!!), and call up Curtis Sanford being mostly decent for 34 games (90.8%). At least Jay McClement and Lee Stempniak made the team and tried their best on a team that stunk. The 2005-06 Blues finished with a record of 21-46-15 for 57 points, dead last in goals for and nearly dead last in goals against.

Making matters worse throughout this nightmarish season was the sale of the team. Before the season, the Lauries had an agreement with SCP Worldwide, an investment group led by Dave Checketts. In November, that offer was withdrawn. In December, negotiations were announced to be with another group called General Sports and Entertainment. When that negotiation period ended, SCP re-entered negotiations. In March, the sale of the Blues and the Savvis Center lease was finally completed to SCP and a private equity firm named TowerBrook Capital Partners. At least the team was finally sold and money could pumped back into the team. This also impacted the front office. Larry Pleau remained as GM, but the team president had plenty of power (more than Pleau, perhaps to make decisions. The Dave Checkkets-led group tabbed former Ranger and broadcaster, John Davidson, to be the new president. Oh, baby.

Davidson missed out on the 2006 NHL Draft, where the Blues picked first overall. They took defenseman Erik Johnson form the USNTDP. With the extra first, they they took Patrik Berglund. Both would play a role in the turnaround. But not immediately. The Blues were very active in free agency in 2006 as they signed Weight back from the Canes, Bill Guerin, Martin Rucinsky, Manny Legace, Radek Dvorak, Jay McKee, and Dan Hinote. So much for a youth movement. But the season would go better, right?

Not right away. The Blues crashed hard out of the gate as they won just 7 of their first 24 games. Mike Kitchen was fired, Andy Murray was named as his replacement. Under Murray, the Blues rebounded and worked their way back up to a decent record by February. The team basically hovered around 50% point hockey and finished the season with a pair of losses to end at 34-35-13 for 81 points. A big improvement over last season to be sure, but still a second-straight playoff miss for a franchise that has not suffered a lot of that.

The decision to bring back Weight was a good one as he did lead the team in scoring with 59 points. The Bill Guerin signing did work out as he put up 28 goals and 47 points. Stempniak broke out with 27 goals and 52 points. David Backes made the team and put up 23 points in 49 games. Legace also proved to be a decent get as his 90.7% total save percentage in 45 games was better than Sanford’s 88.8% in 31 games (ugh) or Bacashihua’s 89.6% in 19 games. However, the team was beset by injuries and so the improvements in both goals for (also not helped by a truly terrible power play that converted about 12% of all situations) and goals against were not enough to get back to the postseason.

At least Pleau (read: Davidson) was able to flip some players into assets as the deadline approached in 2007. Keith Tkachuk was traded to Atlanta for Glen Metropolit, a first rounder in 2007, a third rounder in 2007, a second rounder in 2008, and a first rounder in 2008 if Tkachuk signs with Atlanta (spoiler: he did not). Bill Guerin was sent to San Jose for Ville Nieminen, Jay Barriball, and San Jose’s first round pick in 2007. The most important deal: sending Dennis Wideman to Boston for forward Brad Boyes. This would be recognized next season.

The 2007 NHL Draft would also prove fruitful for St. Louis. Their three first rounders all yielded three still-current NHLers: Lars Eller, Ian Cole, and - the best of the trio - David Perron. The offseason would have the Blues bring back Tkachuk, since he was not going to sign with Atlanta; trading Carl Soderberg to Boston for goalie Hannu Toivonen; signing Paul Kariya to a three-season contract; and giving T.J. Oshie, Perron, and Erik Johnson entry level deals. Sanford, Dallas Drake, and Dvorak went elsewhere. With Jackman and Boyes locked up to four-season contracts, the youth movement continued while still supplementing them with Tkachuk, Weight, and now Kariya.

Kariya would be a valuable signing for 2007-08 as he finished tied for first in team scoring. He was tied with Brad Boyes, who put up a jaw-dropping 43 goals and 65 points in his first season as a Blue. Dennis who? Tkachuk would also be a welcome return as he played a full season and put up 27 goals and 58 points. Stempniak did drop to 13 goals and 38 points. Johnson, Backes, and Perron would play regularly. Weight was not so good to start the season and he was traded to Anaheim with Michael Birner and a 2008 seventh round pick in December for Andy McDonald. McDonald was not just younger, but a great fit for the Blues as he put up 14 goals and 36 points. While the positives were there, there was a lack of scoring outside of Boyes, Tkachuk, and Kariya. The power play was still poor and the team finished near the bottom of the league with 202 goals scored. In net, it was pretty good when Manny Legace played given his total save percentage of 91.1%. Toivonen was terrible in his 23 games with an 87.8% save percentage. Even with the stingy Blues defense, the Blues gave up 232 goals, putting them in the bottom third of the league. And the trades after the Weight-for-McDonald one did not help much. This was the season where Bryce Salvador was traded to New Jersey straight up for Cam Janssen. Which was glorious for the Devils and makes me smile today. The only other trade was sending Christian Backman to New York for a fourth round pick in 2008. Hardly any additions with either deal. Instead of progress, the Blues finished at 33-36-13 for 79 points and still well outside of the playoffs.

The 2008 offseason would prove crucial for future Blues seasons, both in the short term and long term. At the 2008 NHL Draft, St. Louis sent Jamal Meyers to Toronto for a third round pick, which helped made it easy to send a fourth round pick to Nashville on the day of the draft for goaltender Chris Mason. The draft itself had St. Louis select defenseman Alex Pietrangelo at fourth overall, goaltender Jake Allen at 34th overall, and center Jori Lehtera at 65th overall. While these three would not impact the near future, they would after 2008-09. The offseason was spent more on extending McDonald and McClement while giving another season to Tkachuk. With a burgeoning young core and veterans still providing something left in the tank, if they could deepen their attack and secure their goaltending, then the Blues could get back to the playoffs.

The start of the 2008-09 season suggested they would not. First, Erik Johnson would miss the whole season due to injury from a golfing accident. The team started off the season decently, but injuries to McDonald and Manny Legace would send the team tumbling. Legace would return but with a 88.5% save percentage in 29 games, he was not at all effective. In fact, the Blues would waive Legace in February. McDonald would still get to play 46 games and put up 44 points so he was solid. As the team slipped in November, Pleau (read: Davidson) shook things up with a trade. Stempniak was traded to Toronto for Alex Steen and Carlo Colaiacovo. While Stempniak was nearly a point-per-game player, these Steen and Colaiacovo would play larger roles in the future. The trade did not lead to a positive shakeup as the Blues went 4-10-1 in December.

But as the calendar turned, so did the team’s fortunes. The team went on to win 27 games out of 45 in the 2009 portion of the season. Chris Mason stepped up his season to ultimately post a 91.6% in 57 games for the Blues. Boyes was the leading scorer again with 33 goals and 72 points. This season Backes and Perron broke out with 50+ point campaigns. Patrik Berglund hit the ground running on his NHL career with 21 goals and 47 points. T.J. Oshie emerged with 14 goals and 39 points. Roman Polak joined Jackman and Brewer as 20+ minute players on defense. The power play became better, the defense was still strong, and the team remained hot down the stretch of the season. Even with Kariya limited to 11 games, Brewer limited to 28, and no Johnson at all, the Blues battled. They clinched a playoff spot, at home, with a win against fellow-playoff-bubble team Columbus. The Blues would finish the season at 41-31-10 for 92 points and take the sixth seed over Columbus in the West by a tiebreaker. The Blues were back in the playoffs. And if you know the Blues from this era, you will recognize plenty of the names that would be part of their core for the next few seasons: Boyes, Backes, Perron, Jackman, Steen, Coloaiacovo, Johnson and Polak. They seemed set up for success and still had Pietrangelo in the system.

Of course, that is not exactly what happened. The Blues were swept by Vancouver in the first round in 2009 and would then miss the playoff for another two seasons. Coaches were changed (David Payne for Andy Murray), Doug Armstrong took over for Pleau (and took the power back from Davidson), Tkachuk would retire, and the team was in a similar spot to Philadelphia during their drought. They missed the playoffs in each of the next two seasons by five and nine points, respectively. Not exactly a cratering or a reason to tear things down. But the team would get the goods back in 2011-12, built largely on the core formed in this three-season drought. (Oh, and the team was sold again after the 2011-12 season to their current owner, SLB Acquisition Holdings, a group led by Tom Stillman.)

Any Other Thoughts: Ownership issues are apparently a theme for this part. I think only San Jose did not have any that I noticed. But between that and a veteran team not getting any younger or much better, that contributed greatly to their massive failing in 2005-06. Fortunately for the Blues, new ownership was secured fairly quickly, they were willing to spend right away, and they put in a team President who forced Pleau’s hands to make some aggressive moves. What really propelled the Blues back to the postseason, even for the season, was their development of prospects from the drafts just before and during this down period and giving them the support through veterans and coaching. They did not stick with Kitchen, they kept with Murray, and cycling through goalies until finding a solution. They moved players to bring in assets to help or add more prospects; they cycled through goaltenders to get enough saves to go with a stout defense. They did not sit and wait for success; they sought it out. This is closer to a traditional re-build than it may seem. If nothing else, St. Louis showed it could be done within three seasons. Even with falling short the next two seasons, the core formed was solid enough to carry to more sustained success from 2012 onward.

Your Take So Far

Out of the groups of five covered in this series, this group combined for the fewest amount of playoff misses. Just 63 between these five, which surprised me. Two of them are ongoing and may go for longer than this season. Yet it would take another 30 or so combined to catch up with the teams from other parts. This fact alone puts a pin in the notion that success is cyclical and teams have to fall apart before finding success. All five of these teams did make Stanley Cup Finals at one point in their better days. Pittsburgh won multiple Cups, Philadelphia had a pair, and St. Louis got one. If you’re constantly in the mix and continue to work to put together good teams and take acceptable risks to make those teams good, then you can have a run where a franchise misses the playoffs just a handful of times over a long period of time.

The penultimate part of this series will cover the last group of five teams alphabetical order. I am still deciding as to what look at for some of the five. It will definitely include a close look at a period of sadness by the current contenders in Tampa Bay. I have decided that I am going to explore John F. Ferguson’s and Brian Burke’s time in Toronto. Old fans at Pension Plan Puppets are already wincing at those names. Vancouver had three instances of missing the playoffs for four seasons, so there are choices there. It is up in the air whether I do the longest drought for Washington or something more relevant. Part 6 and these super-long posts going into non-Devils team histories will end with Winnipeg. That’s right: The Ex-Atlanta Thrashers. A franchise history that makes the original Jets’ history of mediocrity look great. I think I know which of the two long droughts I will look at. Lastly, I will write up a Part 7 to tie back a lot of the lessons from all of these histories that the Devils should at least acknowledge. Or at least the fans should acknowledge. I am aiming to have that up on the 26th.

In the meantime, what have you learned from this look back at the playoff droughts for the Senators, Flyers, Penguins, Sharks, and Blues? What did you takeaway about those various situations in terms of how they got there and how they did (or did not) get out of them? Did I miss any important details about each of these team’s droughts that have significantly contributed to their struggle or how it ended? If so, what were they? Are you looking forward to Part 6, which will be next week? Please leave your answers and other thoughts about these playoff droughts in the comments. Thank you for reading.