Timeline: The Erik Karlsson Trade

Kyle Dubas can finally rest a little bit easier now that the three-team trade to acquire Erik Karlsson from San Jose is complete.

"When it's a good player that you really want, I think that's why you spend a lot of your nights staring up at the ceiling rather than sleeping, of different ways you can make it happen," said Pittsburgh's President of Hockey Operations and General Manager. "Knowing the market, which other teams are going to jump in, who can beat you to it, how can they beat you to it, how can you outdo them?"

Dubas provided some insight as to how he orchestrated one of the biggest deals in Penguins franchise history when meeting with the media at UPMC Lemieux Sports Complex on Monday.

Over a month earlier, when NHL free agency opened on July 1, Dubas had stood behind that same podium and addressed the rumors about Pittsburgh being interested in the Norris Trophy winner, which had picked up traction that day. Dubas said when a player like that comes available, it's incumbent on him to reach out and see if there's a fit - which got everything started.

"I know it was more of a public thing on July 1 than it had been of late, but I actually think that was more like the opening rounds of the championship fight per se, where it was feeling each other out," Dubas said.

Since the bout for Karlsson began after free agency opened, there was limited cap space for teams. So, even though Dubas said that Sharks general manager Mike Grier was great to deal with throughout the process, figuring out how to make all of the salary components work proved difficult.

There are two things that helped the situation reach a turning point, and Jake Guentzel Video: Kyle Dubas speaks with the media. on Aug. 2 was actually not one of them. Dubas doesn't foresee Guentzel, who's set to be re-evaluated in 12 weeks, being out long enough to be placed on long-term injured reserve (a player must miss at least 10 games AND 24 days). So, the Penguins needed to have room to not only keep his contract on the books, but also have some other space.

It was actually restricted free agent Drew O'Connor Video: Kyle Dubas speaks with the media. with an average annual value of $925,000 before his arbitration hearing, scheduled for Aug. 4, that was one of the catalysts. Settling with the 25-year-old forward triggered the opening of a second buyout window, which would close at noon on Sunday (Aug. 6).

Since Dubas did not want to use that second buyout window to gain cap flexibility - "I think my stance on buyouts has been made clear, I have a strong dislike for them just because they sit on the cap for double the amount of time, and even if they make a great deal of short-term sense, it comes to hurt you in the long run," he said - it placed a self-imposed deadline on the Penguins finding another way to get the space they wanted.

"Which I think was a positive thing for us, really," Dubas said.

While Dubas said there were a few other teams involved at the end, who all had different priorities, Montreal's involvement was the other catalyst that made everything possible. Dubas was impressed with how Canadiens general manager Kent Hughes, a former player agent who used to represent Kris Letang, handled the situation.

"He was very clear and concise on what he was looking to do," Dubas said. "They wanted to jump in and try to help themselves, but also help get this across the line."

Dubas also credited the team around him in the Penguins front office for the part they played, saying their creativity, capability and work ethic shone through during the entire process. Vukie Mpofu, Video: Kyle Dubas speaks with the media. at the end of June, was especially key to making it come together. "He had constant ideas, different things that we could offer and try, through an extremely complicated process," Dubas said of the 27-year-old.

The trade was announced at 11:40 AM on Sunday, just 20 minutes before the second buyout window ended:

- Pittsburgh acquired Karlsson, forward Rem Pitlick, forward Dillon Hamaliuk and San Jose's 2026 third-round draft pick.

"It was a unique opportunity to add a player like Erik, where obviously we had to part with some assets, but we gained more flexibility and added him on at the same time," Dubas said.

- San Jose acquired Pittsburgh's 2024 first-round draft pick (top-10 protected), forward Video: Kyle Dubas speaks with the media., defenseman Video: Kyle Dubas speaks with the media. and forward Mike Hoffman.

"(The Sharks) obviously accomplished their goal of gaining draft choices and greater flexibility as they go through turning their team to where Mike's vision wants to bring it," Dubas said.

- Montreal acquired Pittsburgh's 2025 second-round draft pick, defenseman Video: Kyle Dubas speaks with the media., goaltender Video: Kyle Dubas speaks with the media. and forward Nathan Legare.

"(Hughes) wanted to acquire assets to be in the middle, use his flexibility right now, use what he has to try to accelerate where they're at in their own development," Dubas said. "It was an opportunity to acquire a pick and a really good player to help a team facilitate something else."

For the Penguins, it's one of those deals that feels too good to be true, because it's just that incredible. Bringing in a player of Karlsson's caliber without resorting to any buyouts or completely mortgaging the future was an absolute home run for Dubas and his team.

"Adding someone like that to the group as we attempt to give it every chance to win, but also keep our eye towards the future… we were happy not to include any of our prospects, (like) Owen Pickering and Brayden Yager, in the trade as well, to have them move along," Dubas said. "That was what we're looking to accomplish. That's the way that we went about it."