Pittsburgh Penguins 20 Worst Contracts in the Salary Cap Era
My rule that Stanley Cup champions are disqualified from having bad contracts (at least the deals they were under at the moment of victory) created some challenges, especially with the Pittsburgh Penguins. The Crosby-Malkin dynasty was a stunning success, to the point where players who had extended stays and DID NOT win a title could almost be considered bad investments for no other reason. That might be a ridiculous standard to set, but Ron Hainsey, Trevor Daley, Olli Maatta, and Mark Streit, proved in 2017 that the generational talents can win titles with subpar pieces around them. Ergo, if you played with them and did not win, something must be wrong with you.
That’s my theory anyway. Otherwise, their worst contracts list would have been impossible to build back in 2020. A majority of the deals on this list were signed after their last championship in 2017. I desperately needed them to get knocked out of the 2020 Covid Cup, or the previous iteration would have been decimated beyond repair. In the last few years, management gave me more to work with, so it’s starting to look like a real worst contracts list. As you can see from the rankings report card below, this list is down near the bottom of the badness ranks, and one of the most recent. They’ve been paying so much to their top stars for so long, leaving less money to spend on mistakes around them.
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 The book is still available on Amazon, though some of the stats on active contracts are now out of date.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 September 1st, 2024: Adjusted for $88M cap, added Ryan Graves and Tristan Jarry, demoting Bryan Rust and Evgeni Malkin.
1. Rob Scuderi
Adjusted Cap Hit: $17.4M, $4.4M (avg)
Value Returned: $5.3M, $1.3M (avg)
% Earned: 30%
“Let’s face it, I’m a plug. I play good defence, I’m going to move the puck tape-to-tape when I can, and when I don’t have an opportunity to, I’m going to put the puck in the safest areas. It’s not the prettiest thing in the world, everyone knows that. But it can be effective.”
Rob Scuderi defected from the Pittsburgh Penguins a few weeks after winning the Stanley Cup in 2009, to join the LA Kings. While he was gone, the Pens struggled in the playoffs and LA won a championship. So Ray Shero can be forgiven for being eager to get Scuderi back on the roster when he returned to free agency. Unfortunately, at this point he was a year too old and it wasn’t long before he simply was no longer good enough to play D in the NHL.
After two failed playoffs with both Crosby and Malkin healthy, Jim Rutherford somehow managed to dump this turd on the Chicago Blackhawks, in one of the worst trades of Stan Bowman’s GM career (as an aside; for a GM with 3 Stanley Cup rings, Stan Bowman has a surprising number of bad trades on his resume). Bowman did flip him back to Los Angeles for the last year of Christian Ehrhoff. The Kings allowed Scuderi to play out the last season in the AHL.
2. Jack Johnson
Adjusted Cap Hit: $17.6M, $3.5M (avg)
Value Returned: $7.1M, $1.4M (avg)
% Earned: 40%
“I've been really wanting to be part of a winning culture and a place where the expectations to win are as high as they could be."
“He was a healthy scratch at the end of the season. I know the reason why. It wasn't because of how he was playing."
"No one wishes anything bad to happen to him and his family. We wish him the best. But for him to put it the way he put it today is bulls---. And to have a general manager question our decision-making from three hours away, he must be a f---ing magician."
Jack Johnson’s departure from the Columbus Blue Jackets was anything but cordial, as the veteran defenseman had been a healthy scratch at the hands of John Tortorella at the end of his previous contract. Johnson inked a 5-year ticket with the Penguins at age 31 on July 1st 2018 and commented that it was great to join a winning culture, intentionally accidently implying that the Blue Jackets did not have a winning culture under Torts. That set off some beautiful Canada Day fireworks.
One red flag that seems to be repeating itself as I’m building these worst contracts lists is “long term deal + over 30 years old + over 1000 career hits”, and Jack checks all the boxes. Johnson no longer skates particularly well, is not good at moving the puck, and most of his teammates are demonstrably worse when Jack is on the ice. Over the first two seasons, Sidney Crosby had a 45% expected GF% when on the ice with Jack, but 58% when they were apart. It’s the same with Johnson’s primary D partner Kris Letang. Rutherford bit the bullet and bought out the last 3 years.
3. Zbynek Michalek
Adjusted Cap Hit: $27.7M, $5.5M (avg)
Value Returned: $16.4M, $3.2M (avg)
% Earned: 58%
“I was pretty clear about addressing our defence. By getting Paul Martin and Zbynek Michalek, I think we’ve done that.”
Zbynek Michalek came to Pittsburgh as an unrestricted free agent in 2010 with a similar contract to what Brooks Orpik had signed 2 years earlier (Anton Volchenkov signed a nearly identical deal with the Devils that same day). The Czech defenseman had scored 28 PTS for the Coyotes in 2009, dropping to 17 PTS before hitting the open market. Paul Martin also inked a new ticket that day, but you can read more about that further down the list.
The Penguins did manage to get decent usage out of Michalek for those 2 seasons, but had disappointing playoff defeats (including a first round exit in 2012 with both Crosby and Malkin healthy). Shortly afterwards they sold him to the Coyotes for a 3rd round draft pick. The downside of this contract was relatively small for the Pens, who shipped him out for good value. Michalek would go on to have trouble staying healthy, so it was the Coyotes who got the worse return on their investment.
4. Patric Hornqvist
Adjusted Cap Hit: $28.7M, $5.7M (avg)
Value Returned: $14.4M, $2.9M (avg)
% Earned: 50%
“We wanted those five years, and we got it. I’m happy about that. I’m going to be trying my best here for five years. That was the key for me here in this deal.”
Patric Hornqvist scored 14 playoff goals over the course of 2 Stanley Cup championship runs, but still had only eclipsed 70 regular season games once in his 6 years with Pittsburgh. Injuries had already started creeping into the equation before he signed this 5-year extension at age 31, and his health would become an increasing problem as he grew older.
The Swedish winger saw both his scoring output and ice time decline in year one, where his primary skill became the net front presence on the power play, while being a liability 5 on 5. Getting onto the ice for that devastating Pittsburgh power play was the reason he was still scoring any PTS. He was flipped after year two to the Florida Panthers for another bad contract in Mike Matheson. In the final 2 seasons, his scoring rate dipped below 40 PTS per 82 GP as his body broke down. He barely played in year five.
5. Ryan Graves
Adjusted Cap Hit: $27.2M, $4.5M (avg)
Value Returned: $11.0M, $1.8M (avg)
% Earned: 40%
Ryan Graves became an unrestricted free agent at age 28 after 5 NHL seasons, primarily regarded as a defensive defenseman but produced well offensively in New Jersey before hitting the open market. Kyle Dubas was hired one month earlier with a mandate to extend the Crosby-Malkin-Letang window and put them back in the playoffs. Graves was seen as exactly the type of player needed to accomplish that mission, but buying this type of asset on July 1st requires paying a premium (my modelling priced his 2022/23 stat line $1M less than actual). That premium might have been worth the price had he continued at his previous level and helped the Pens into the playoffs.
Sadly for Sid, that’s not what happened. Graves ice time dropped by 1.5 minutes per game and his scoring rate nearly cut in half. The team missed the playoffs for the 2nd consecutive season and suddenly that Crosby-Malkin-Letang window may already be slammed shut. There are 5 full seasons remaining at the time this was written, so being proven wrong is entirely plausible. But I’ve been doing this long enough that my instincts in this case feel correct. This type of deal to this type of player at this age rarely works out well.
6. Tristan Jarry
Adjusted Cap Hit: $27.1M, $5.4M (avg)
Value Returned: $22.0M, $4.4M (avg)
% Earned: 81%
On the same day that Kyle Dubas inked Ryan Graves, his number one goalie was also hitting the open market and none of the available replacements were a safe bet to boost the playoff mandate. He had already proven the ability to provide mostly competent goaltending for 40-60 games behind this roster. Sadly for Sidney, that competence diminished, the team struggled until Jarry was replaced with Nedeljkovic, then they caught fire and made a run at the wildcard. Giving a goalie 5x5 demands they be a quality #1, not backing up the back-up down the stretch. Elvis Merzlikins notwithstanding, only the elite tier of goalies sign for 5+ years at a wage this high.
While Jarry finished year one with 51 games played and only slightly below average save percentage, the season was a failure. He was benched when it mattered most and the team missed the playoffs. There is still lots of time remaining for him to prove me wrong and get them back into the playoffs, but I’m not terribly concerned.
7. Jeff Carter
Adjusted Cap Hit: $6.6M, $3.3M (avg)
Value Returned: $2.5M, $1.3M (avg)
% Earned: 38%
Jeff Carter did experience a scoring resurrection after coming to Pittsburgh at age 35, getting a 10+ bump in PTS per 82 GP with his new team, seeing his ice time increase to 17.7 minutes per game. It was sufficient to supply Ron Hextall with the confidence to make a 2-year gamble on this aging asset. Well Father Time went a few rounds with Jeff in the summer of 2022, because he was a significantly worse player upon his return, resulting in a 4-minute drop in average ice time. Many speculated that the Penguins would buy out the second season, but they opted to bring him back for one final kick at the can. It was unlikely he’d find the fountain of youth.
8. Brock McGinn
Adjusted Cap Hit: $11.5M, $2.9M (avg)
Value Returned: $4.2M, $1.1M (avg)
% Earned: 38%
Brock McGinn had played his entire career with the Carolina Hurricanes when he became an unrestricted free agent in July 2021, mostly playing the role of a bottom-six grinder. According to my expected free agent value algorithm, he had never once been worth the salary that Ron Hextall paid him (but did come within $500K in 2018). He battled injury issues in year one, then saw his ice time significantly reduced in year two. They were able to find a buyer at the 2023 trade deadline, moving McGinn and a 3rd round pick to rent Dmitri Kulikov, who only played 6 games for the Penguins, who missed the playoffs. There are worse mistakes than paying $2.8M for a guy worth $1.2M, but my options for bad contracts (that didn’t win Stanley Cups) was pretty thin here. Given that most seasons most of their cap was tied up in their superstars, there wasn’t really much left aside to waste.
9. Andre Roy
Adjusted Cap Hit: $5.6M, $1.9M (avg)
Value Returned: $2.3M, $0.8M (avg)
% Earned: 41%
"It was never our intention or our desire to lose Andre Roy in the first place; however, when the new CBA was put in place we knew that in a salary cap world we could not afford to match what some teams were going to be prepared to pay Andre and thus we lost him to unrestricted free agency"
Andre Roy became an unrestricted free agent after winning the Stanley Cup with Tampa in 2004, and received a substantial over-payment from Craig Patrick. Roy became a regular healthy scratch who averaged only 5 minutes per game of ice time when he did make the line-up.
This was a waste of money and would have produced a better return on their investment had they used that cash as toilet paper. After Ray Shero became General Manager, the enforcer was demoted to the minors. He was eventually claimed by Jay Feaster on re-entry waivers, telling the media that he never wanted to lose Roy in the first place.
10. Jocelyn Thibault
Adjusted Cap Hit: $6.1M, $3.0M (avg)
Value Returned: $1.9M, $0.9M (avg)
% Earned: 30%
''Jocelyn brings a wealth of experience to our goaltending corps and will help us tremendously as we move forward"
Jocelyn Thibault had the best season of his career in 2003 at age 27, where he posted a .915 SV% in 62 GP and appeared in the All-star game. He would miss 60 games the following season after hip surgery and did not play during the lockout. Due to provisions in the new CBA, he was still RFA and the Penguins traded a 4th round pick to acquire his rights from Chicago. There’s not going to be a ton of demand for a 30-year-old goalie with a reconstructed hip, but Craig Patrick made a 2-year commitment so that he could serve as the French-Canadian mentor to Marc-Andre Fleury.
Thibault put up terrible numbers in year one with a 4.46 GAA. In just 16 games he won only once while allowing 12 more goals than league average. His season ended early with (insert dramatic pause) a hip injury. Over 2 seasons he had 8 Wins, 17 Losses, with a 3.52 GAA and an .894 SV%. That's a fail. Perhaps we can consider the overpayment to be a “mentoring fee” that proved to be a success when Fleury became a Stanley Cup champion.
11. Ryan Whitney
Adjusted Cap Hit: $36.4M, $6.1M (avg)
Value Returned: $34.4M, $5.7M (avg)
% Earned: 95%
“They’re paying me a lot of money and I’m not playing”
When Ryan Whitney signed this contract in July 2007, it was the most money awarded to a defenseman under the age of 27 since the salary cap was introduced two years earlier. Ryan banked $24M, where Niklas Kronwall had banked $15M one year earlier. Whitney proved to be a trend setter, as several young defensemen would sign some version of this deal in the decade that followed. Granted, this is also an example of how injury related deterioration can sour an investment, more evidence to the cautionary tale of the risks of long-term contracts.
Whitney did have a few good seasons under this treaty, but it took a downward spiral after he went to Edmonton. The Penguins shipped him out of town shortly before they won the Stanley Cup in 2009, bringing in Chris Kunitz, who won 3 championships in Pittsburgh (you never ever hear Whitney mention that on his podcast). Ryan did not last long in Anaheim before they flipped him to Edmonton for Lubomir Visnovsky. Both the Pens and Ducks were able to trade this contract for quality assets before the bottom fell out.
Whitney did run into lower-body injury problems that contributed to his decline. Over the full 6 seasons he averaged 41 PTS per 82 GP, which isn’t terrible. The problem was that he played 51 games or less in 4 of 6 years.
12. Darryl Sydor
Adjusted Cap Hit: $8.2M, $4.1M (avg)
Value Returned: $3.7M, $1.8M (avg)
% Earned: 45%
“It’s all you can do. Be ready when you’re asked to go and make the most of your opportunity.”
Darryl Sydor was 35 years old when he became an unrestricted free agent on July 1st 2007, agreeing to a 2-year ticket with Pittsburgh. His days of challenging for 50 PTS were in the rear-view mirror, scoring 21 PTS in 74 GP at age 34.
Darryl’s batteries were running dangerously low, earning reduced deployment, contributing very little to the offense and earning several healthy scratches in the 2008 playoffs. The Pens were able to dump him on the Dallas Stars in a mutual bad contract exchange for Phillip Boucher (who did not contribute much to Pitt in the playoffs either).
13. Justin Schultz
Adjusted Cap Hit: $18.5M, $6.2M (avg)
Value Returned: $9.4M, $3.1M (avg)
% Earned: 50%
“Justin plays a very important role for our team. It's very good to know that he will be returning to us for the next three years.”
During his first full season with the Pittsburgh Penguins at age 26, Schultz scored a career high 51 PTS, plus 13 more PTS in the playoffs to win his 2nd Stanley Cup with the team. He signed this extension while the party was still bumping a few weeks later. Jim Rutherford offered a high enough price that Schultz was willing to concede 2 years of unrestricted free agency. They paid for a 50-point player and got much less than that.
Yes, injuries factored into the failure of the Justin Schultz contract, but even when healthy he scored far below the 54-point pace he posted in his contract year when they won the Stanley Cup. He finished with 34 PTS per 82 GP, which is roughly equivalent to what you’d expect from a $3.5M defenseman. Coincidently, Justin signed a 2-year deal with rival Washington when this expired at a $4M cap hit.
14. Mark Eaton
Adjusted Cap Hit: $5.8M, $2.9M (avg)
Value Returned: $2.5M, $1.2M (avg)
% Earned: 42%
"I take pride in, No. 1, playing good defense and shutting down whoever I’m playing against. I have a good grasp of the defensive game, but I’m willing and able to do more. Offensively, I think there’s still a lot more for me to contribute. I plan to get better at that aspect, as well."
Mark Eaton joined the Pens as a 29-year-old unrestricted free agent after having suffered a serious wrist injury a few months earlier. He was mostly a defensive player with negligible offensive contributions and ran into further injury problems.
When they had a healthy Eaton in the in the 2007 playoffs, they lost in 5 games to the Ottawa Senators. Next year he missed the playoffs after ACL surgery, and the Pens made it all the way to the Stanley Cup final. He played 76 games and scored 6 PTS over 2 seasons. They were a better team without him on the ice.
It should be noted that he wasn’t that bad of a player, considering he signed a new contract after this expired and helped them win the 2009 Stanley Cup.
15. Conor Sheary
Adjusted Cap Hit: $10.2M, $3.4M (avg)
Value Returned: $6.5M, $2.2M (avg)
% Earned: 64%
"We talked as well about a one-year term, but I think the three-year term worked out better for myself where I could have a little security and put a three-year body of work together where I can play hockey and not worry about a contract every year. I was very happy with that."
Conor Sheary posted a whopping 53 PTS in 61 GP in 2016/17 to earn this contract, but the magic dried up once he stopped playing regularly with Sidney Crosby. He had peaked at 45 PTS in the AHL, as Sid squeezed more juice out of him than what should have been possible. It eventually proved to be a mirage.
The good news once again is that Jimmy Rutherford has a talent for trading away his contract mistakes, and he bundled up this one with a terrible Matt Hunwick contract and shipped the duo off to Buffalo for a 4th round pick. Buffalo was thinking that he could play with Eichel given his experience with Crosby, that proved to be a big mistake. Jimmy did re-acquire Conor at the end of the contract and he helped the team miss the playoffs.
16. Matt Hunwick
Adjusted Cap Hit: $7.6M, $2.6M (avg)
Value Returned: $3.0M, $1.0M (avg)
% Earned: 40%
“There's a lot of things that go into making a decision like this, and certainly you have to think about your family when you have a wife and a son and a dog and those kinds of things. You kind of couple everything together and if you have a chance to be on a really good team, it was just a no-brainer for me."
– Matt Hunwick
Matt Hunwick had enjoyed a long career as a journeyman depth defenseman who reached his peak offensively as a rookie in 2009 when he posted 27 PTS in 53 GP. At age 28 he even found himself mired in the AHL during what should have been his peak years of production. At age 31, Hunwick posted the 2nd best offensive season of his career, scoring 19 PTS with Toronto to earn this generous offer from Jim Rutherford.
It was a gaffe, but one that Jimmy rectified when he shipped Matt to Buffalo in the Conor Sheary trade for a 4th round pick. It’s more likely that Rutherford insisted that Hunwick get included in the trade, not the other way around. I can’t imagine that Jason Botterill wanted this asset. That’s a big price tag for a healthy scratch. The final season was spent on IR.
17. Paul Martin
Adjusted Cap Hit: $34.5M, $6.9M (avg)
Value Returned: $29.9M, $6.0M (avg)
% Earned: 87%
"We’ve got a great corps of defencemen right now that are signed for a number of years. They’re at the right age. From our staff and coaches’ standpoint, we’re pretty thrilled."
Paul Martin signed with the Pittsburgh Penguins one year after they won the Stanley Cup, earning himself a big-ticket deal after regularly topping the 30-point threshold with the New Jersey Devils. Paul struggled in his second season, after which Shero called him into his office to ask if he wanted out, which Paul declined.
On paper the Martin contract does get a passing grade that peaked during the lockout shortened season of 2013. He suffered a broken hand at the 2014 Sochi Olympics, which also marked a turning point in his effectiveness. His ice time and point production began to drop after that. This is not a terrible contract, but by Penguins standards, it’s one of their worst. Five seasons in the prime years of Crosby and Malkin and zero Stanley Cups. By my criteria that means failure.
18. Brandon Tanev
Adjusted Cap Hit: $22.3M, $3.7M (avg)
Value Returned: $9.4M, $1.6M (avg)
% Earned: 42%
“He’s a really good skater. He’s a good penalty killer. He’s a guy that when he’s playing makes the team harder to play against.”
Brandon Tanev was an effective 3rd liner for the Jets and was in demand as a free agent, but I’m skeptical that anyone was offering this much term, going to his 33rd birthday. The 6-years may have just been a way to massage down the cap hit, as the back half aligns with the back-diving portion of Crosby’s contract, when the team might not be expecting to be competitive.
Year one certainly proved to be a success, as the Penguins 4th line was very effective in 2020, albeit not terribly productive offensively. He was later taken by Seattle in the expansion draft, and missed much of his first year. There’s an argument that this isn’t even bad, it’s just slim pickings for Pens worst deals. Kinda bad is enough to crack the list.
19. Jamie Oleksiak
Adjusted Cap Hit: $7.1M, $2.4M (avg)
Value Returned: $5.5M, $1.8M (avg)
% Earned: 78%
“We felt that his game was coming along. We still see more of an upside to him, but when you can get a guy that size with that strength to play in your top-six on defense, he can do some things that a lot of other players can’t.”
Jamie Oleksiak had a career year at age 24 in Pittsburgh, scoring 17 PTS in 68 GP after being traded from Dallas for a 4th round pick. This prompted the Penguins to give him twice as much money as he’s realistically worth and he was a frequent healthy scratch in the first year of the deal.
The good news for the Pens is that they were able to ship Oleksiak back to Dallas in year one of the deal for that same 4th round pick, the bad news is that gave them the flexibility to go out and acquire a terrible Erik Gudbranson contract. Jamie was surprisingly good for the Stars in the 2020 Covid Cup, helping them come to within 2 wins of a title, which would have bounced him from this list.
20. Ryan Rust
Adjusted Cap Hit: $31.3M, $5.2M (avg)
Value Returned: $39.5M, $6.6M (avg)
% Earned: 126%
“His leadership qualities and experience as a two-time Stanley Cup champion is an important piece of our team.”
I’m not sure what’s a bigger risk, signing a 30-year-old player to a 6-year contract or me including it on this list before a sufficient number of games had been compiled under its tenure. The Penguins championship window may have closed, but the window for them to continue trying to win with Sidney Crosby was still open. This pact is clearly all about maximizing that short-term window, but Rust would have needed more money if this was only going to be a 4-year offer.
Given that Sid Crosby is unlikely to be playing for this entire 6-year span, management probably isn’t terribly concerned that this could be painful for the last few years, as it allowed them to lower his annual cap hit and give the team more flexibility in their competitive window. A sufficiently big reward was required for Rust to forgo an opportunity to test the open market for what could be his last contract in the NHL.
UPDATE: Scoring rate jumped from 47 per 82 GP up to 74, which boosted the long-term projection above last summer when this looked like it would be worse. We’ll see what happens next season, but it may need to be removed if he sustains.
Pending: Evgeni Malkin
Adjusted Cap Hit: $25.1M, $6.3M (avg)
Value Returned: $27.8M, $6.9M (avg)
% Earned: 111%
“His hockey resume and individual accomplishments speak volumes about him as a player, and we are thrilled to watch him continue his remarkable legacy in Pittsburgh.”
Do you really need me to convince you that signing a soon to be 36-year-old player with an injury history to a 4-year treaty is an inherently risky investment? Perhaps it would have been prudent to wait for Malkin to start sucking before including this here, as he was scoring at a point per game clip in year 1 (at least was at the time this was written), so that possible decline clearly has not started. In the final year of his previous deal, Gino scored 42 PTS in 41 GP after missing the first half of the season with injury.
For a while it looked like Pittsburgh management wasn’t interested in taking on a risky contract and was prepared to let him leave. At least until Sidney Crosby lobbied for Gino to return, ostensibly forcing management to oblige their beloved captain. We’ll see how well this ages, but if he continues at a point per game clip for the next 4 years, it might need to be moved to their best contract list.