Sunday night, Penguins president of hockey operations Kyle Dubas could settle in for a decent night’s sleep, something that has seldom happened lately.
For six weeks, Dubas typically stirred as he sought a little slumber. Visions of Erik Karlsson in black and gold skated through his head. More often, though, his brain still whirred and whirred, processing all the possible machinations of a trade that could finally get the Norris Trophy-winning defenseman to Pittsburgh.
“You spend a lot of your nights staring up at the ceiling rather than sleeping, [thinking] of different ways you can make it happen,” he admitted Monday.
Dubas and the Penguins finally made it happen on Sunday morning, executing a complicated three-team trade that brought Karlsson to Pittsburgh and shipped four regulars and a pair of premium draft picks to San Jose or Montreal. Somehow, the Penguins actually cleared $3.1 million in salary cap space, too.
With 12 total assets being exchanged among the three teams in the deal, it was the largest trade in Penguins history, per team historian Bob Grove.
So after the Penguins initially started their pursuit of Karlsson at the NHL draft in Nashville in late June, how did the stunning deal ultimately come together Sunday, during a quiet period in the NHL offseason? Dubas shed light on that process at a Monday press conference at UPMC Lemieux Sports Complex.
After he returned from Nashville, Dubas had a lengthy to-do list, even after trading for winger Reilly Smith. He had to lock in a No. 1 goalie, which he did by bringing back Tristan Jarry. He homed in on big blue-liner Ryan Graves at the onset of free agency. Dubas made a flurry of signings those first 24 hours.
Meanwhile, trade discussions with the Sharks and their general manager, former NHL tough guy Mike Grier, got serious on July 1. Some inside the organization felt the Penguins came very close to landing Karlsson that afternoon.
But Dubas compared those initial talks to the early rounds of a heavyweight bout, saying in hindsight that Dubas and Grier were “feeling each other out.”
One thing quickly became clear to Dubas and the revamped Penguins front office: With a third team likely needing to be involved and little financial wiggle room after all of their moves in free agency, finding a solution that satisfied both the Penguins and the rebuilding Sharks was going to require some creativity.
Dubas said Vukie Mpofu, hired as director of hockey operations and legal affairs in June, was constantly pitching him “different things we could offer.”
“It was a very complicated process with San Jose and with other teams involved,” Dubas said. “And Vukie continually showed me throughout ... this process — but also during free agency — that he is capable of taking on a lot more.”
Dubas said the Penguins maintained regular communication with the Sharks. But even as other Karlsson suitors dropped out of the running — Seattle, Carolina and Dubas’ former team in Toronto were all reportedly in the mix at some point — Dubas worried somebody would swoop in and steal Karlsson.
“I think you always think that,” the 37-year-old executive said, chuckling. “I don't know, maybe there's a paranoia that just goes with this. When it's a good player that you really want, I think you always have to operate like that.”
Despite that, Dubas stayed patient and stood his ground. So did the Sharks.
One of the biggest sticking points from San Jose’s perspective was the retention of salary. With an $11.5 million cap hit over the next four seasons, Karlsson is one of the NHL’s highest-paid players. Grier said he was unwilling to retain much of his salary. In the end, the Sharks ate just $1.5 million per season.
“Kyle was aggressive, but Kyle was really willing to make some concessions on his stand to make this whole thing work,” Grier said Sunday on a conference call with Bay Area reporters. “Both sides made concessions on not only the retention number but the package in general, just to get the deal done.”
Last week, talks intensified when Drew O’Connor’s contract situation was resolved and Jake Guentzel’s ankle surgery created an artificial deadline for Dubas.
When the Penguins settled their arbitration case with O’Connor, signing him to a modest two-year deal, it created a brief buyout window for the Penguins, who wanted to create more wiggle room after losing Guentzel. Dubas had until noon Sunday to buy out a player. Mikael Granlund was the obvious candidate.
“We really never ever want to get to that point,” Dubas said of a potential buyout. “I think my stance on buyouts has been made clear. I have a strong dislike for them. ... So we knew we had that kind of timeline there. And that’s how the injury to Jake and the O’Connor settlement both kind of collided.”
With increased urgency and both sides willing to concede a little ground to make a trade happen, Dubas and Grier worked to loop in a third party. It ended up being the Canadiens, who saw an opportunity to take advantage of their own salary cap situation. Dubas indicated Montreal “came in at the end.”
In exchange for Pittsburgh’s second-round pick in 2025, Montreal agreed to take back defenseman Jeff Petry and goalie Casey DeSmith. The Penguins also gave them forward prospect Nathan Legare, who fell out of favor here.
Last summer, Petry pushed for a trade out of Montreal to reunite with his family in the U.S. But Dubas said Montreal wasn’t on his 15-team no-trade list.
The Penguins also acquired veteran forward Rem Pitlick from the Canadiens.
“I was really impressed with Kent [Hughes],” Dubas said of the second-year GM, who was a long-time player agent before joining the Montreal front office. “He was very clear and concise on what he was looking to do in terms of acquiring assets to ... try to accelerate where they’re at in their own development.”
Montreal agreed to take on $6.5 million in salary between Petry and DeSmith.
With that financial hurdle out of the way, Dubas could finalize with San Jose the compensation package for Karlsson, who last season won his third Norris Trophy and was the first defenseman in three decades to reach 100 points.
The Penguins hung on to top prospects Brayden Yager and Owen Pickering and sent a conditional 2024 first-round pick to the Sharks. If that pick somehow lands in the top 10, the Penguins can send them their 2025 first instead.
The Sharks tossed a 2026 third and prospect Dillon Hamaliuk into the trade.
“San Jose, they’ve got tremendous flexibility and a great group of young players forming there. And we’re in a different spot than both of those teams,” Dubas said. “So I thought it was something that worked out well for everybody.”
Especially the Penguins, who added another All-Star in Karlsson to hopefully help them make another run at the Stanley Cup during the Sidney Crosby era.
It took significant effort and many sleepless nights, but Dubas got his guy.
“It was a unique opportunity,” he said. “We obviously had to part with some assets, but we gained more flexibility and added him at the same time. ... He’s still an elite player, as he showed last year winning the Norris Trophy. If we have a chance to add him, we’re going to do it because we believe in the group.”
Matt Vensel: mvensel@post-gazette.com and Twitter @mattvensel.
First Published: August 7, 2023, 8:18 p.m.
Updated: August 8, 2023, 9:54 a.m.
