Philadelphia Flyers 20 Worst Contracts in the Salary Cap Era
Paul Holmgren was the Philadelphia Flyers longest tenured General Manager in the salary cap era, winning 7 playoff series, including a Stanley Cup finals appearance. While Paul might have been responsible for most of their success, he was also liable for their greatest blunders, which peaked with Ilya Bryzgalov in 2011. Holmgren was fired within a year of Ilya’s contract getting bought out. A legendary Flyers enforcer Ron Hextall was awarded the top job in 2014, but was never able to win a playoff series. Among the team’s problems was finding reliable goaltending, which was partially to blame for how they ended up with Bryzgalov in the first place.
As we learned with the Rangers, great goaltending can cover up massive mistakes elsewhere on the roster, and Philly may finally have found a winner in Carter Hart (sorry that last part was written before Carter Hart became a criminal (allegedly)). Eventually Chuck Fletcher would replace Hextall in 2018, and made enough contributions to this list that he was eventually fired too and replaced with a player who signed one worst contracts in Flyers history. Danny Briere is the current GM and has yet to sign a deal that breached the worst 20. One notable achievement on their rankings report card, #1 in total AHL games played while under contract. Congrats…
This was originally published in my 2020 book The Definitive Guide to Salary Mismanagement, and has now been updated with new contracts. I will continue to update each team’s list every summer going forward. The rule is that only active contracts can move up or down. Expired deals cannot pass each other (with a few exceptions). The book is still available on Amazon, though some of the stats on active contracts are now out of date. You may yet find it interesting because there were detailed stat graphics that you won't find here. One thing you won't find here are entry level contracts because they all come from the same cookie cutter and require less skill at the negotiating table.
Updated August 29,2024: Adjusted for $88M cap. Sean Couturier was considered for addition, but ultimately the jury required an extra season of deliberation. Travis Sanheim was moved to #20 and could be removed entirely in the future if the power play time sustains.
1. Ilya Bryzgalov
Adjusted Cap Hit: $52.4M, $5.8M (avg)
Value Returned: $13.9M, $1.6M (avg)
% Earned: 27%
“You guys just here to blame someone. You never look yourselves in the mirror, eh? You're always good. You never make the mistakes. Your articles are always perfect. In reality, what have you done for this city? If you ask yourself, what have you done besides only criticize? Not much.”
“I am who I am. Life is too beautiful to be sad, to be depressed. The sun comes up every day and it's beautiful.”
Ilya Bryzgalov had been in the Vezina trophy conversation for the previous 2 seasons (78 wins + 35 goals saved above average) before reaching the open UFA market for the first time at age 31. The Flyers won the bidding process, though you’ll never hear anyone involved in this debacle claim victory. The Flyers opted to offer a ridiculous 9-year term that would take him to his 40th birthday in an attempt to lower his annual cap hit. Year one was almost average, posting 38 wins, 16 losses with a 2.48 GAA and .909 SV%, which was borderline decent for his compensation rate (that was before posting an .887 SV% in 11 playoff games).
By year two, his play had eroded further, and his relationship with the Philadelphia media became contentious. After 99 regular season GP with -20 goals allowed below average, management decided to pull the plug, using one of their compliance buyouts afforded by the new CBA. They did not want to risk this situation spiraling any further down the toilet bowl. But you don’t need to feel bad for Ilya, he’ll be collecting $1.6M per year until 2027. Elon Musk will be walking around on Mars before Ilya’s Flyers cheques stop coming…
2. Daniel Briere
Adjusted Cap Hit: $76.3M, $9.5M (avg)
Value Returned: $35.8M, $4.5M (avg)
% Earned: 47%
"Danny had many offers and lots of interest out there. He made sure to carefully look at his options. He is thrilled with the results."
Daniel Briere cashed in on one of the best pre-UFA seasons of the salary cap era, scoring 95 PTS in 2007 before reaching the open market. The Flyers made the winning bid with $52M ($71.4M adjusted for cap inflation, and their costly new asset depreciated right out of the gate, with Danny dropping down to 72 PTS in 79 GP in year one; not exactly terrible, but a disturbing cost to benefit ratio nevertheless. A pair of abdominal injuries derailed his 2nd season, after which is scoring output declined even further.
By year six he scored 16 PTS in 34 GP (39-point pace), prompting management to exercise a compliance buyout freeing themselves from the final 2 years. Overall, Briere scored 64 PTS per 82 GP, which would almost be defensible if you weren’t paying an average adjusted cap hit of $8.9M. Montreal believed he had some juice left in the tank and signed him to a 2-year deal, which you can read about on the Canadiens worst contracts list.
Note: this was written before Briere became GM, otherwise it would have been mentioned.
3. Andrew MacDonald
Adjusted Cap Hit: $35.6M, $5.9M (avg)
Value Returned: $13.5M, $2.3M (avg)
% Earned: 38%
"We believe he's going to make our team better. With an eye on the future, we have an interest in keeping Andrew longer term.”
Andrew MacDonald had a career year before he was due to become an unrestricted free agent, scoring 28 PTS while averaging 24.6 minutes of ice time per game. The blueliner had long been logging heavy minutes for the Islanders, enticing Holmgren to trade 2nd and 3rd round draft picks to acquire him as a rental in 2014 (he played some playoff games and they were bounced in the first round).
Those draft picks turned into Ilya Sorokin and Brandon Carlo, a heavy price to pay considering they could have just waited until July 1st and made him an offer then. Five weeks after arriving in Philly, Holmgren signed MacDonald to this long-term extension. Year one was a disappointment, but he finally started to put some numbers on the scoresheet in year two, scoring 36 PTS in 43 GP for the Philadelphia Flyers Lehigh Valley Phantoms in the AHL. He was bought out after year five.
4. Scott Hartnell
Adjusted Cap Hit: $35.2M, $5.9M (avg)
Value Returned: $21.5M, $3.6M (avg)
% Earned: 61%
"Scott has been a very good player for us over the last five seasons and we look forward to many more good years to come."
Scott Hartnell was wrapping up a 6-year contract played out entirely in Philadelphia, including a trip to the Stanley Cup final, where he had become a fan favourite. Holmgren signed him to an extension 11 months early after Hartnell had just scored a career best 67 PTS at age 29. This is a classic example where it would have been in a team’s best interest to wait until after the season to extend a pending 31-year-old UFA, because when play resumed after the 2012 lockout, Scotty’s scoring rate fell dramatically, scoring 11 PTS in 32 GP (28-point pace).
The outlook got bleak before the clock even started counting down on this investment, a 6-year deal to a 31-year-old declining player. Hartnell did still have some gas left in the tank, scoring 60 PTS in year two for the Columbus Blue Jackets, after his contract was flipped for another over-priced declining asset, RJ Umberger. Hartnell scored just 37 PTS in 78 GP in year four before being bought out.
5. Vincent Lecavalier
Adjusted Cap Hit: $28.4M, $5.7M (avg)
Value Returned: $5.7M, $1.9M (avg)
% Earned: 20%
“I’m open to Montreal. But I’m not closing the door on anyone. The door is open for everyone and after that we’ll see.”
Paul Holmgren overpaid for a 33-year-old forward with deteriorating skills who had just been bought out from his previous terrible contract. Vinny was far removed being an elite scorer, but had still been producing at a 60-point pace over the previous few seasons, all of which were cut short due to injury. In year one Lecavalier scored 20 goals and 37 PTS, which was the closest he came to earning that pay cheque under this pact (still $2M overpaid).
Year three yielded just 18 PTS in 49 GP and was described by a friend of mine; “watching Lecavalier skate is like watching a baby deer learning how to walk”. In 2016 he was traded to Los Angeles (with Luke Schenn) under the pretense that he would retire at the end of the season. The Flyers actually got Jordan Weal and a 3rd round pick in return, which was a respectable return given how badly LeCavalier had been producing.
6. James van Riemsdyk
Adjusted Cap Hit: $37.9M, $7.6M (avg)
Value Returned: $21.7M, $4.4M (avg)
% Earned: 57%
"There were a couple different teams in the mix, I'm happy to be coming to Philadelphia, and I think it's going to be a great fit."
James Van Riemsdyk managed to score a career best 36 goals before reaching UFA market, and scratched a lottery ticket from the team that drafted him, albeit for less term than he would have been seeking. Other teams might have been offering more term for a lower salary, like $35M over 7 years to massage the cap hit down to $5M, but better to get your money up front if you can. It’s worth pointing out that his 2017/18 stat line was worth approximately $5M in expected free agent salary. While JVR did have a career best goal scoring season before leaving Toronto, there were reasons to be concerned about his career trajectory, mainly steadily decreasing ice time for 4 straight years (down to 14.9 in his career year).
Over his first 2 seasons in Philly, JVR scored at a 55-point pace, which generally costs $5M, and often found himself on the 3rd line. His scoring is generally been erratic, where he disappears for long stretches then scores in bunches. He found himself becoming a healthy scratch in the 2020 bubble playoffs. That’s a big price tag to watch games from the press box.
7. Kevin Hayes
Adjusted Cap Hit: $52.5M, $7.5M (avg)
Value Returned: $24.9M, $3.6M (avg)
% Earned: 47%
“He plays a smart, two-way game and is just entering the prime of his career. Kevin will add size and skill to our lineup."
Kevin Hayes scored a career high 54 PTS at age 26 before becoming an unrestricted free agent, never before or since breaching the 50-point barrier. Realistically he should have been worth in the ballpark of $5M, maybe $5.5M max. The fact that Philly paid him $7.1M was confusing from the day it was signed.
In year one of this contract, he regressed down to 41 PTS in 69 GP, which was worth approximately $5M. Years two and three had stat lines valued at $4.2M and $2.8M. If this had been for $5M, it would not be on this list. Those were supposed to be years that they got the most out of him.
8. Rasmus Ristolainen
Adjusted Cap Hit: $26.1M, $5.2M (avg)
Value Returned: $7.1M, $1.4M (avg)
% Earned: 27%
“It's difficult to get physical defensemen, never mind physical, right-shot defensemen. There were other teams that were offering similar type of packages to ours and we had the highest pick, so we got him.”
The Flyers paid a steep price to acquire Rasmus Ristolainen from Buffalo, sending 1st and 2nd round draft picks with 1 year left before he was set to become an unrestricted free agent. His scoring rate declined from 45 to 30 PTS per 82 GP in just 3 seasons before the trade. Then he was moved to Philadelphia and his offensive output declined even further, down to 20 PTS per 82 GP.
That stat line was worth approximately $3.5M, but the Flyers wanted to extend him before he even had a chance to reach the open market, and that always comes with a wage premium. This has the potential to climb even higher on the list in future updates as it potentially deteriorates further.
9. Derian Hatcher
Adjusted Cap Hit: $26.2M, $6.6M (avg)
Value Returned: $10.7M, $2.7M (avg)
% Earned: 41%
“I know the Flyers are a very good, competitive team and that's another thing that weighed in on my decision. I truly feel that they are out to win at least a Stanley Cup. That's what I know about them."
The ink was barely dry on the new Collective Bargain Agreement when Bobby Clarke signed a trio of 6’5 235-pound defenseman all on the same day (including Mike Rathje and Chris Therien). This might have jived with the Broadstreet Bullies mindset that the Flyers and their fans cherished. The bad news was, the NHL was also introducing new rules to crackdown on obstruction/holding and taking out the 2-line pass to open up the game.
Bobby really couldn’t read the tea leaves on where the NHL was going after the lockout. Hatcher never had the foot speed to play in a world without clutching and grabbing. He was a dinosaur by the time Philly landed the behemoth. At least some of the burden was eased by LTIR in the final year.
10. Matt Read
Adjusted Cap Hit: $17.9M, $4.5M (avg)
Value Returned: $7.6M, $1.9M (avg)
% Earned: 43%
“He’s one of the young core players on our team. He’s a valuable member of our hockey team, and we’re happy to have him under contract for the next five years with this extension.”
Matt Read scored 49 PTS per 82 GP as a rookie, and that scoring rate reliably dropped every year for the next 7 seasons (including all 4 years of this pact). Holmgren signed Read to this extension in September, 8 months before he was set to become an unrestricted free agent and Paul would be replaced as GM before this contract even started.
Year one saw Read drop to 30 PTS in 80 GP, and that output only shrank as the deal grew older, finishing with a single point in 19 GP in year four when he was demoted to the AHL for 33 games.
11. Denis Gauthier
Adjusted Cap Hit: $11.6M, $3.7M (avg)
Value Returned: $2.5M, $0.8M (avg)
% Earned: 23%’
"I knew my job was going to be tougher to keep with all the changes being made and the media talking about me as a salary dump"
The Flyers obtained Denis Gauthier in a trade with Arizona Salt Lake City before he was set to become an unrestricted free agent, paying a steep price of two 2nd round draft picks. Bobby Clarke retained his services with this overly generous salary for a guy playing bottom pairing minutes (16.5 per game).
Gauthier never received any acclaim at the pro level for being an offensive defenseman, and was not acquired to fulfill that function. Although he did show some flashes of offensive aptitude in year two scoring 18 PTS in 76 GP for the Philadelphia Flyers Phantoms in the AHL. Philly then gave up another 2nd round pick to dump his salary on the LA Kings, where his ice time dropped even further. This marked the end of his NHL career. All in, they burned three 2nd round picks on this failed experiment.
12. Nicklas Grossmann
Adjusted Cap Hit: $18.6M, $4.6M (avg)
Value Returned: $6.9M, $1.4M (avg)
% Earned: 38%
“I heard the criticism, but I don't really want to comment on that. I think our guys have really come together here. It's a great group, a lot of young guys and older guys stepping up and being leaders.”
The Flyers dealt 2nd and 3rd round picks to Dallas to secure Nick Grossmann as a rental before he became an unrestricted free agent and locked him into an extension a few weeks later prior to reaching the open market. Those draft picks turned into Devin Shore and Jake Guentzel, a steep price to pay. This was another acquisition that the Flyers were purchasing for defensive purposes, as Nick’s career high was 12 PTS at the time.
Nicklas was deployed in more of a shut down role, which might explain why he averaged under 10 PTS and 45 Shots per season over these 4 years. His production warranted a salary half this size, and was eventually traded to the Arizona Salt Lake City Coyotes as part of the Chris Pronger salary dump.
13. Mike Rathje
Adjusted Cap Hit: $31.6M, $6.3M (avg)
Value Returned: $6.9M, $1.4M (avg)
% Earned: 22%
"I am really excited, actually. It is kind of going to be an awkward position for me because I was in San Jose for such a long time and I have never been through this before. I am sure things will work out in Philadelphia. I am definitely going to make their blue line solid. I can play every night and play 25 minutes a game and maybe add a little bit of offense.”
Mike Rathje had been patrolling the blueline for the San Jose Sharks for 10 years before becoming an unrestricted free agent after the lockout, landing in Philly. Signed on the same day as Darian Hatcher, he was another big slow old defenseman added at a time when the league was introducing rules to make this type of player obsolete, or at least a greater liability.
Frankly the impact of this mistake could have been far greater had an injury not prematurely ended his career in year two. The 24 PTS he scored in year one wasn’t terrible, but they were paying him the 2022 equivalent of $7.4M to post pedestrian numbers. The Flyers were saved by LTIR.
14. Dale Weise
Adjusted Cap Hit: $10.9M, $2.7M (avg)
Value Returned: $3.3M, $0.8M (avg)
% Earned: 31%
“I think I can fit anywhere. I fit in the top nine, maybe I’m kind of a middle-six guy. I can play in the top two lines if you need me, if there’s injuries, if you don’t have anyone else in line. I’m very comfortable playing on the third and fourth line. I think I can do a little bit of everything.”
Dale Weiss had consecutive seasons in Montreal where he scored at a 30-point rate, by far the best totals of his career, before becoming an unrestricted free agent. He didn’t have to wait long for a contract, landing this beast on July 1st opening day, courtesy of Ron Hextall. Dale would score 23 PTS in 112 GP in Philly before they decided to ship him back to Montreal in exchange for a bad David Schlemko contract that the Flyers bought out soon afterwards.
If the Habs were hoping that Weise would recapture the magic he’d shown before leaving, they would be seriously disappointed. By the final year he was playing predominantly in the AHL. Dale liked to brag that he fit anywhere in the line-up, and yeah, he was so versatile that he also fit on the minor league roster.
15. Philippe Myers
Adjusted Cap Hit: $8.2M, $2.7M (avg)
Value Returned: $4.0M, $1.3M (avg)
% Earned: 48%
“It's an honor to be a part of the Flyers for the next three years and I'm really looking forward to it.”
Once upon a time Phil Myers was a blue-chip prospect that management openly declared was completely off the table in any trade talks. He might have gone undrafted, but turned heads playing for Team Canada at the next World Junior tournament. He was never able to play a full NHL season on his entry level contract, in part due to injury. The final year, he scored 16 PTS in 50 GP, which my algorithm priced at $2.1M.
It wasn’t exactly a large overpayment, but it started to become clear that he was not the player many expected him to be. One year in, Philly traded him to Nashville for a good return (at least if Ryan Ellis had been healthy). Once in Nashville, Myers was basically a utility player until they moved him to Tampa in a mutual salary dump.
16. Braydon Coburn
Adjusted Cap Hit: $23.8M, $5.9M (avg)
Value Returned: $11.9M, $3.0M (avg)
% Earned: 50%
“I've been here a long time. I'm glad it worked out. It was a good process and it's nice to have it done so I can focus on hockey, not that I wasn't before but it's always nice to have it done. It's an honor to be part of something special like the Flyers."
Braydon Coburn was set to become an unrestricted free agent when Holmgren opted to retain him on this extension in November. While he never did make it to July 1st, the Flyers did need to offer him generous enough terms to forgo an opportunity to hit a big home run in the summer. Coburn peaked at 38 PTS at age 22, and his offensive output had mostly been in decline ever since.
The big defenseman played 22.6 minutes per game in year one, and that number shrank each season down to 16.8 in year four. The Flyers were able to trade Coburn to Tamps for a nice return of Radko Gudas plus 1st and 3rd round draft picks. He finished with 43 PTS in 238 GP (15 PTS per 82 GP) at an average adjusted cap hit of $5.5M. Coburn did prove to be a useful player who helped Tampa advance to the Stanley Cup final in 2015, he was simply paid twice as much as he was worth.
17. Michael Raffl
Adjusted Cap Hit: $8.3M, $2.8M (avg)
Value Returned: $3.2M, $1.1M (avg)
% Earned: 38%
“I knew it was a contract year for me, so I was kind of getting a little rattled in the beginning, like not scoring, and that never helps. You hold your stick a little too tight. I still got my scoring chances. That didn’t change at all. I didn’t think it affected my game that much. When you don’t score as much, obviously your confidence drops and stuff. It wasn’t my best year producing wise, I think.”
Michael Raffl scored a career high 31 PTS in 2016 before he was set to become an unrestricted free agent at age 27. He came to Philly as an undrafted free agent at age 24 in 2013 and fired off 21 goals as a sophomore. Ron Hextall did not want the Austrian to leave in free agency and gave him a 3-year extension in February.
Raffl’s scoring rate dropped by nearly half in year one, potting just 11 PTS in 52 GP before an MCL tear ended his season. He would bounce back to score 22 PTS in year two, but that’s still half the production that you would expect for that pay grade. By year three Raffl was dropped to the 4th line. He would return for Philadelphia after this expired, but for a reduced price.
18. Oskar Lindblom
Adjusted Cap Hit: $9.6M, $3.2M (avg)
Value Returned: $3.7M, $1.2M (avg)
% Earned: 38%
Oskar Lindblom was an inspiration to the hockey world when he overcame his Dec 2019 cancer diagnosis and the team awarded him a very generous contract at the end of that season. He had never been worth that much money at any point in his career, so perhaps the team was making a charitable donation to an inspirational player that they hoped was beginning a fruitful career in Philadelphia. But alas, hockey is a cut-throat business and Lindblom took a big step backwards in 2021, recovering slightly in 2022, but still not living up to that price tag, so the team bought him out. What have you done for me lately.
19. Nolan Baumgartner
Adjusted Cap Hit: $4.3M, $2.2M (avg)
Value Returned: $1.6M, $0.8M (avg)
% Earned: 36%
Nolan Baumgartner scored an improbable 34 PTS (22 on the power play) with the Vancouver Canucks in 2004 (having never played more than 9 games in a season at age 29). When he became a free agent at the end of the season, Bobby Clarke came sniffing around looking for an exciting young puck mover. He only played 6 games for the Flyers and 125 games in the AHL. Spoiler alert, this is substantially more money than you should be paying an AHLer. That success in Vancouver was just a mirage, but Bobby took the bait.
20. Travis Sanheim
Adjusted Cap Hit: $50.3M, $6.3M (avg)
Value Returned: $46.9M, $5.9M (avg)
% Earned: 93%
This contract was earmarked for this list before a single game was played, but for most of his career he was approximately a $4M defenseman (according to my algorithm), so going 8 years for a 27-year-old at $6.3M has a very high associated risk premium. He finished 19th in my 2023 worst NHL contract Twitter poll tournament, as my followers agreed that the risk is unlikely to be worth the desired reward. He has never played much on the power play, and players generally don’t acquire that ability beyond this age if they haven’t already. He could prove me wrong, but I’m not too worried. This might be ranked higher in future updates.
Update: He improved in year one, thanks to an expanded role on the power play. This was demoted a few spots and may be removed entirely and a public apology issued if it persists.