The best and worst non-entry level contracts the Penguins have signed in the salary cap era is all about championships. They’ve won 3 of them, and I’ve got a rule against putting contracts that won Cups on worst contracts lists. If you got paid a good salary and played with Crosby and Malkin in the playoffs, you better have won a Cup. Ron Hainsey, Trevor Dailey, Olli Maatta, Mark Streit, proved in 2017 that the generational talents can win titles with sub-par 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 the Penguins worst contracts list would have been impossible to build.
1- Sidney Crosby, 12 years $104M: ($109M adjusted for cap inflation)
Signed by Ray Shero, June 28 2012, Start age: 26
This contract has produced 2 Stanley Cup wins and 2 playoff MVPs and it’s not even over yet (although at this point it seems unlikely the Pens are winning any more Cups in the Crosby era). Anytime you can get the best player in the world for less than the league maximum, you’re doing great. At this point it really doesn’t matter what happens on the back end of this contract because the team has already received the best possible value attainable. The Cap Recapture penalty won’t be an issue. If Sid so much as gets a headache in 2022, they can put him on LTIR.
2- Sidney Crosby, 5 years $43M: ($56.3M adjusted for cap inflation)
Signed by Ray Shero, July 7 2007, Start age: 21
The Penguins may have only won 1 Stanley Cup over these 5 years, but Crosby did score 371 PTS in 257 GP, which translates to 118 PTS per 82 GP. That’s well worth whatever the price you paid. When you can get the best player in the world, no price is too high (well under a hard salary cap anyway…not sure he’d be worth a billion dollars, close, but not quite). Sid missed time with injury in years 2 and 3, which also produced the best point per game values of his career.
3- Evgeni Malkin, 5 years $43.5M: ($54.8M adjusted for cap inflation)
Signed by Ray Shero, July 2 2008, Start age: 23
The score of this contract is elevated by a fantastic 2011/12 season that saw Malkin win the Hart Trophy for league MVP. Anytime you can get one of those, it’s worth whatever the price you paid. His other seasons on this contract were hampered by injuries, which limited his upside but still managed to produce 97 PTS per 82 GP. The Penguins did not get a Cup out of this contract, but the MVP is always a steal. It’s hard to put a price on guys this good.
4- Evgeni Malkin, 8 years $76M: ($79.7M adjusted for cap inflation)
Signed by Ray Shero, June 13 2013, Start age: 28
Malkin made a substantial contribution to 2 Stanley Cups victories with 54 playoff PTS and counting. Arguably he could have been named playoff MVP in 2017 if not for Crosby. He was a bit of a disappointment in year one with 70 PTS in 69 games and had mediocre regular seasons in the 2 championship years. In 2018 he jumped up to 98 PTS and has averaged 92 PTS per 82 over the first 4 years of the contract.
5- Kris Letang, 4 years $14M: ($17.2M adjusted for cap inflation)
Signed by Ray Shero, May 30 2010, Start age: 23
In the first year of this contract Letang nearly doubled his point production up to 50 PTS in 82 GP, while averaging close to 24 minutes per game, quickly becoming the Penguins best defensemen. Not surprisingly, injuries did limit the maximum potential of this deal, where he averaged 61 PTS per 82 GP at a bargain price. This may not have produced any Cups, but he did notch 31 PTS in 41 playoff GP.
6- Kris Letang, 8 years $58M: ($60.8M adjusted for cap inflation)
Signed by Ray Shero, July 2 2013, Start age: 27
Letang has had issues staying healthy on this contract, but has still produced 65 PTS per 82 games, averaging over 25 minutes per game of ice time. He played a key role in their 2016 Stanley Cup championship, and missed the 2017 playoffs with an injury. At age 31 in 2019 he is showing no signs of decline.
7- Marc Andre Fleury, 7 years $35M: ($45.2M adjusted for cap inflation)
Signed by Ray Shero, July 3 2008, Start age: 23
Fleury won a Stanley Cup in year one and had a regular season Win-Loss record of 246-122 with a 2.44 GAA and .914 SV % with a +19 Goals Saved Above Average rating. He also helped me win a fantasy hockey championship under this contract, which is what I will always remember him for. The funniest part is that when I made the trade to acquire him that season, it was originally vetoed by the league with people complaining that I was getting ripped off. I politely let everyone know that they were all idiots (I was trading both goalies from a terrible Leafs team and Vanek for Fleury). Eventually I managed to get the trade pushed through, changed my team name to UNLEASH THE FLEURY, won the championship, and had a very satisfying last laugh.
8- Brian Dumoulin, 2 years $1.6M:
Signed by Jim Rutherford, July 9 2015, Start age: 24
This contract did not qualify as a result of offensive production, it’s for how heavily they leaned on Dumoulin to play important minutes for 2 Stanley Cup victories at a bargain price tag. Try finding another 2-year contract in the salary cap era that won championships both seasons (hint: he’s the only one). Dumoulin played 22 minutes per game in the 2017 playoffs without Letang in the line-up.
9- Justin Schultz, 1 year $1.4M:
Signed by Jim Rutherford, July 13 2016, Start age: 26
Anytime you can get 50 PTS from the blueline for $1.4M, that’s a win. He also added 13 PTS in the playoffs winning the Stanley Cup. Schultz was coming off a 64 GP, 18-point season, then doubled his production, playing a key role in the 2017 title with no Letang in the line-up. The Pens traded a 3rd round pick to acquire him from Edmonton, and it paid off.
10- Alex Goligoski, 3 years $5.5M: ($7.2M adjusted for cap inflation)
Signed by Ray Shero, June 17 2009, Start age: 24
Goligoski took his game to the next level after signing this contract, and scored 113 PTS in 223 GP at a bargain price. They traded this contract to Dallas in year two for James Neal and Matt Niskanen, which turned out to be good value even though neither Neal or Niskanen won Stanley Cups in Pittsburgh.
11- Ian Cole, 3 years $6.3M: ($7.2M adjusted for cap inflation)
Signed by Jim Rutherford, June 29 2015, Start age: 26
The first two years of this has produced 2 Stanley Cups, where Cole played an important role. He was very dependable in the playoffs. It only cost them Bortuzzo and a 7th round pick to get him from St. Louis, then they traded him after 2 championships as part of the Derek Brassard acquisition (which in retrospect was not a great transaction). Cole didn’t play nearly as many minutes as Dumoulin in those championship playoff runs, but still played a key role in 2017 when they lost Letang.
12- Max Talbot, 2 years $1.3M:
Signed by Ray Shero, July 5 2007, Start age: 23
He scored the game winning goal in game 7 of the Stanley Cup finals, producing all of Pittsburgh’s offense in the clinching game. If that were the only game he played on this contract, it would still have made this list. He may have only scored at a 29-point pace in these 2 regular seasons, but managed a 44-point pace in the playoffs.
13- Jordan Staal, 4 years $16M: ($20.3M adjusted for cap inflation)
Signed by Ray Shero, Jan 1 2009, Start age: 21
Staal was a good player for the Penguins, who shipped him off to Carolina instead of signing him to a big new contract, getting Dumoulin, Brandon Sutter (who was later traded for Nick Bonino), and a 1st round pick (which they whiffed on Derrick Pouliot). That’s not a great return considering the draft pick flopped, but they did acquire pieces that helped them win 2 championships, so that’s good. Over these 4 seasons he averaged 56 PTS and 20 minutes of ice time per 82 games.
14- Sergei Gonchar, 5 years $25M: ($40.9M adjusted for cap inflation)
Signed by Craig Patrick, Aug 3 2005, Start age: 31
Gonchar was the backbone on the blueline for 2 Penguins trips to the Stanley Cup final before Letang had emerged as their top guy. Logged a ton of ice time and remained very productive into his mid-30s, averaging 66 PTS per 82 GP. Also chipped in 44 playoff PTS in 60 GP.
15- Chris Kunitz, 3 years $11.5M: ($12.8M adjusted for cap inflation)
Signed by Ray Shero June 27 2013, Start age: 34
Just a reminder that this list was an incredibly difficult to assemble given my criteria of contracts that win Cups being ineligible. Most of these would not have appeared on a worst contracts list had they been signed by almost any other team (I had a similar issue building the Chicago and Los Angeles Worst Cons lists).
1- Rob Scuderi, 4 years $13.5M: ($15.4M adjusted for cap inflation)
Signed by Ray Shero, July 5 2013, Start age: 34
Scuderi left for Los Angeles after winning a Stanley Cup with the Penguins in 2009. While he was gone, the Pens struggled in the playoffs and LA won a championship. So it did make some sense why Shero was eager to get him 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- Zbynek Michalek, 5 years $20M: ($24.2M adjusted for cap inflation)
Signed by Ray Shero, July 1 2010, Start age: 27
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.
3- Andre Roy, 3 years $3M: ($5.4M adjusted for cap inflation)
Signed by Craig Patrick, Aug 4 2005, Start age: 30
This was a waste of money and would have produced a better return on their investment had they used that cash as toilet paper. One year was bad enough, but for some strange reason they gave him three. The good news came when the Lightning claimed him off waivers in year 2, taking a bad investment off their books. Not worth a roster spot. Played on a team with Sidney Crosby and missed the playoffs.
4- Matt Hunwick, 3 years $6.8M: ($6.9M adjusted for cap inflation)
Signed by Jim Rutherford, July 1 2017, Start age: 32
Forgive me for calling this one a failure before it’s had a chance to finish, but half way through Hunwick is already playing AHL games. Yet once again a bad contract has been shipped out of town before its end, with Rutherford dumping this one on 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.
5- Paul Martin, 5 years $25M: ($30.3M adjusted for cap inflation)
Signed by Ray Shero, July 1 2010, Start age: 29
On paper the Paul Martin Penguins 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 seems to mark the 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.
6- Jocelyn Thibault, 2 years $3M: ($5.7M adjusted for cap inflation)
Signed by Craig Patrick, Aug 10 2005, Start age: 30
Thibault was brought in to provide a veteran back-up for Marc Fleury and 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. Played on a team with a healthy Sidney Crosby that missed the playoffs. Over 2 seasons he had 8 Wins, 17 Losses, with a 3.52 GAA and an .894 SV%. That's a waste of money, even more so in a world with a $39M salary cap.
7- Jack Johnson, 5 years $16.3M:
Signed by Jim Rutherford, July 1st 2018, Start age: 31
This contract qualified for the Penguins worst contract list before a single game had been played. Call this a gut feeling. There wouldn’t have been a problem had they made this a 2 year deal in the same $3M AAV range, but the 5 year term poses a problem in the future. Teams need to be careful giving that much term to a declining 31-year-old defenseman. It may take a year or two before Penguins fans start lamenting this contract, but trust me, they will before the end.
8- Darryl Sydor, 2 years $5M: ($7.4M adjusted for cap inflation)
Signed by Ray Shero, July 2nd 2007, Start age: 35
Shero signed this veteran defenseman too late in his career when he was no longer an effective player. This is yet another example where the Pens were able to trade a player right before winning a Stanley Cup, sending him to Dallas for Phillip Boucher (who did not contribute much to Pitt in the playoffs either). Darryl did not do much for the money he was paid.
9- Mark Eaton, 2 years $3.2M: ($5.4M adjusted for cap inflation)
Signed by Ray Shero, July 3rd 2006, Start age: 29
SHe played 71 games and scored 6 PTS over 2 seasons for $5.4M (cap adjusted). The Pens were eliminated in 5 games by the Senators in the playoffs with Eaton as their 3rd defenseman. The next season Eaton didn’t even play in the playoffs and the Penguins made it to the final. They were a better team without him on the ice.
10- Ryan Whitney, 6 years $24M: ($32.2M adjusted for cap inflation)
Signed by Ray Shero, July 1st 2007, Start age: 24
Whitney did have a few good seasons under this contract, 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. He 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 injury problems with his foot that contributed to his decline. Over the full 6 seasons he averaged 41 PTS per 82 GP for a cap adjusted AAV of $5.4M. That’s not terrible value. The problem was that he played 51 games or less in 4 of 6 years.
11- Christian Ehrhoff, 1 year $4M: ($4.6M adjusted for cap inflation)
Signed by Jim Rutherford, July 1 2014, Start age: 32
If you are going to strike-out on a contract to a 32 year old player, best to do it on a 1 year deal. They gambled that Ehrhoff still had some offense left in the tank coming out of his Buffalo buyout, but they were wrong. He had 14 PTS in 47 GP and did not win a Cup playing on a team with a healthy Crosby and Malkin. Sure, he had some injury issues, but even when healthy he was not good this season. Ehrhoff’s career only lasted one more season after this (which included time served in the AHL) before returning to Europe.
12- Gary Roberts, 1 year $2.5M: ($3.9M adjusted for cap inflation)
Signed by Ray Shero, June 22 2007, Start age: 41
At age 41 Roberts did not have much left in the tank, despite I’m sure great conditioning. He played 38 games scoring 3 Goals, averaging just over 13m per game of ice time.
13- Marcel Goc, 1 year $1.2M: ($1.4M adjusted for cap inflation)
Signed by Ray Shero, July 1st 2014, Start age: 31
They thought they were buying a 25-point player and they got a 9-point player. The cap hit was relatively small, so we can’t call this a costly mistake. This is often the best kind of mistake to make because the consequences are small. The Pens traded him to St. Louis for Max Lapierre, who wasn’t much better. Neither Goc or Lapierre played in the NHL again after the 2014/15 season.
14- Zigmund Palffy, 1 year $4.5M: ($9.1M adjusted for cap inflation)
Signed by Craig Patrick, Aug 7 2005, Start age: 33
As far as bad contracts go, this one ain’t so bad. Only 1-year term and Ziggy popped in 42 PTS in 42 GP. It’s important to note that with a $39M cap that season, his salary equates to $9.1M in 2019. The Penguins missed the playoffs, which has been very rare in Crosby’s career. Palffy only made this list because I’m running out of bad contracts to list here. The pickings are slim for a team with so many championships.
15- Dick Tarnstrom, 1 year $1.6M: ($3.2M adjusted for cap inflation)
Signed by Craig Patrick, Aug 29 2005, Start age: 30
This is not a significant waste of money, but 14 PTS in 55 GP and missing the playoffs on a Crosby team is enough to make the list.