Every general manager makes mistakes.
For many reasons, even the best plans can implode. This player doesn't work out because his game doesn't fit the team's needs, or he washes out because he's unhappy about being traded, or just bad luck. The Pittsburgh Penguins and their GMs have had plenty of successes in the last 40 years, and they've had their gaffes, but there have also been a few inspired escapes from bad situations.
Recent Penguins GMs have played the Houdini role several times.
There have also been plenty of attempts, but some have not been very successful. After all, future Penguins Hall of Fame inductee Jim Rutherford shuffled the cards more than a single-deck blackjack dealer. Later in his tenure, he was chasing mistakes with more mistakes, but early on, he essentially traded up from an eraser to a Ferrari, leading to a pair of Stanley Cups.
Current Penguins GM Kyle Dubas has also had a few escapes from trouble. And current Edmonton Oilers GM Stan Bowman dubiously makes a couple of appearances on the list.
Top 5 Penguins Escapes
5. Alexei Kovalev
If you're an older Penguins fan, you may remember Petr Nedved demanding a healthy payday from a Penguins franchise so financially bereft that it did everything short of looking for loose change beneath the arena seats. So, in 1998, the Penguins traded Nedved and a couple of others to the New York Rangers for out-of-favor winger Alexei Kovalev.
That worked out pretty well. Patrick escaped a potentially crippling situation and came out much better on the other side.
Including a second run that lasted only 20 games at the end of his career in 2011, Kovalev played six electrifying seasons with the Penguins, tallying 151 goals and 354 points in 365 games. Removing the last 20-game stint in which he had just seven points, he was more than a point-per-game player in a Penguins sweater.
Kovalev's totals are exponentially more impressive, considering they were set during the "dead puck" era of clutching and grabbing and neutral-zone trapping.
4. Tristan Jarry trade
What got the Penguins into trouble was signing Jarry to a five-year contract on July 1, 2023. The goaltending market had fewer options than a Soviet bread line, and the Penguins banked on being able to help Jarry get over his inconsistency.
Jarry did become more consistent, but not in a positive sense. The rest of his Penguins tenure was marked by early-game goals against, injuries, and unspoken friction. Former coach Mike Sullivan probably still has nightmares about "first shot, first goal."
Jarry sailed through waivers in January 2025, and it seemed his time with the club was done, with more than three years remaining on his deal. However, he rebounded to begin the 2025-26 season, and Dubas didn't hesitate to rid himself of the risk via a Penguins trade with Bowman and the Oilers last December.
In retrospect, it was brilliant. In the moment, it was a bit of an eyebrow raise to trade a starting goalie on the upswing in exchange for a goalie on the outs, a depth defenseman, and a second-rounder. The end result was huge financial savings and the ability to sell a player at the height of his value before a major crash.
Jarry swooned in Edmonton, but the Penguins freed space for prospect Sergei Murashov , saved millions, and found Stuart Skinner , whose puck-stopping helped the Penguins make the playoffs and whose presence added a jolt of positivity to the room.
3. Dan Muse, Erik Karlsson
Dubas and Sullivan agreed it was time to part ways following the Penguins' third straight playoff miss in 2024-25. Dubas's signature acquisition was Erik Karlsson on Aug. 6, 2023, but the three-time Norris Trophy winner was awash in mediocrity with the Penguins, and it looked like a failed attempt to revive the Penguins.
However, Dubas escaped the dour feeling that had spread throughout the organization by moving on from Sullivan's decade-long tenure and finding a diamond-in-the-rough coach who immediately earned respect and trust and added a realistic level of optimism.
Muse also connected with Karlsson, who submitted his best campaign as a Penguin and one worthy of Norris Trophy votes.
Muse also revitalized the team that was frustrated and frustratingly underachieving. His impact on the 2025-26 Penguins is hard to quantify because the environment was so rich and different that any carryover from the past was gone within the first hours of training camp.
Honorable Mention: Many will also cite Dubas's trade for Karlsson as an escape. The Penguins gave up a first-round pick, Jan Rutta , and Mikael Granlund (as well as sending Mike Hoffman from Montreal to San Jose as part of the three-way deal in which salaries were held).
However, Granlund has been a productive player in San Jose, Dallas , and Anaheim , averaging .6 to .86 points per game, and the first-rounder surrendered in the deal became the 14th overall selection in the 2024 draft. In the big picture, the escape was more of a real hockey trade.
2. Carl Hagelin
Rutherford whiffed on his attempt to acquire a scoring winger for Sidney Crosby or Evgeni Malkin during his first year on the job. Rutherford zipped a first-round pick and Rob Klinkhammer to the Edmonton Oilers for struggling scoring winger David Perron .
That was the whoops.
Perron continued his scoring slump with the Penguins, and by the middle of 2015-16, Rutherford took a machete to the overgrowth of his first-season mistakes.
On Jan. 16, 2015, Rutherford was in the midst of a revamp. He fired coach Mike Johnston in December, followed by a stunning trade, and then dumped the slow Perron to the Anaheim Ducks for their new zippy free-agent acquisition, Carl Hagelin, who wasn't working out despite signing a four-year, $16 million deal.
Hagelin was a perfect fit for the new speed-oriented Penguins and quickly formed the HBK line with Nick Bonino and Phil Kessel , which became the backbone line of their 2016 Stanley Cup run.
Hagelin's game was never about the stats, though he put up fair numbers in the playoffs. His game was about speed, penalty killing, and a relentless forecheck that kept opposing defensemen in constant trouble.
1. Trevor Daily
Former GM Ray Shero figured that if one Rob Scuderi tenure was Stanley Cup-worthy, then a second tenure at the end of his career would be the tonic needed to bring the horribly underachieving and petulant Penguins back to Stanley Cup glory.
In 2013, Shero signed the then 34-year-old to a four-year contract with a $3.375 million cap hit. That was the mistake from which the Penguins needed to escape. They were now cap-strapped and carrying Scuderi, who had painfully passed his expiration date.
The contract was an absolute albatross as Scuderi's skating slowed further, and he became a lightning rod for fan frustration, which was a shame for a player whose defensive game and leadership had been so vital to both the previous Penguins' and LA Kings ' Stanley Cup success.
Rutherford found his Huckleberry in Bowman on Dec. 2, 2015. Rutherford traded Scuderi to the Chicago Blackhawks for elite skating defenseman Trevor Daley , who was frustrated with Chicago coach Joel Quenneville's restrictive defensive system and had given the team an ultimatum: Use me or trade me.
Chicago traded him, and that move is still paying dividends: Daley quickly became a popular teammate and a dynamic defender in Sullivan's speed-oriented scheme. Trading Scuderi was thought to be absolutely impossible, but Rutherford foraged a valuable player who was vital on the back-to-back Stanley Cup run of '16 and '17.
Daley remains with the organization as a special assistant to Dubas.
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