Sidney Crosby, Evgeni Malkin, and the Pittsburgh Penguins tried their best, but it was eventually too late for them. After being knocked out of the Stanley Cup Playoffs by the Philadelphia Flyers, the Pens turn the page into the NHL offseason and there’s one major question the franchise must answer: where will Malkin play in 2026-27?
“Just so appreciative for the opportunity to have played with them as long as we have. Hopefully, we can keep going,” Crosby said after the playoff elimination from the 2025-26 NHL campaign, via Pens Inside Scoop. “It’s kind of hard to put into words, honestly. We probably have just gotten used to. I think they’re like family. We’ve had some great wins, some tough losses like this.”
Crosby’s statement was a clear message to the organization and the higher ranks in the front office, including president of hockey operations Kyle Dubas. Still, the Penguins will take their time before coming to a final decision on Malkin, who will turn 40 before the 2026–27 NHL season. In fact, Malkin will be the same age as Dubas when the puck drops in October.
Crosby, Malkin, and Letang: ‘The Big Three’
Crosby, Malkin, and Kris Letang have played together for the past 20 seasons in the NHL. No other trio in North American sports history has been together for as long as the “Big Three” in Pittsburgh. Ask any of the three, and they hope to keep the streak going in the 2026–27 season.
Evgeni Malkin #71 of the Pittsburgh Penguins.
However, at some point, the front office must decide what’s best for the organization. Malkin is set to become an unrestricted free agent (UFA) in the summer, and although Dubas has admitted there’s interest in a reunion, anything can happen.
If it were up to Crosby, the decision would be made in a heartbeat, though he understands the business side of it and doesn’t take these past two decades for granted. Obviously, the trio has led Pittsburgh to three Stanley Cup conquests (2009, 2016, and 2017).
Where do the Penguins go next?
Entering this season, many expected it to be a sort of last dance for the “Big Three.” Making the postseason was a surprise, and the belief in the City of Bridges was that the trio could pull off one last improbable deep run. In the end, Crosby, Malkin, and Letang did their job but couldn’t overcome the lack of depth in Pittsburgh, and the young Flyers squad ultimately took them out in six games, in identical fashion to their first-round elimination by Philly in 2012.
Now, the dilemma is even harder for the Penguins. Should they call it a career for the “Big Three,” or have the three veterans proven to be part of the solution? Whichever route Dubas and company go down, only time will tell whether it was the right move or not.
For as much success as Crosby and company have had, the past few years have been anything but kind to fans in Pittsburgh. Moreover, extending Malkin may only be clawing at and holding on to the last thread of the glory days in the City of Bridges. It might have lost its grace and may be seen as more of a last-ditch effort than a tribute to the franchise’s active heroes..
Might be time to move on
Since hoisting back-to-back Stanley Cups in 2016 and 2017, the Penguins have only won a single playoff series. That was back in 2018. Since the Washington Capitals knocked them out of the second round, en route to their Cup conquest, the Pens haven’t been the same.
Pittsburgh has been bounced in the opening round five times since (including once in the qualifying round in the 2020 Stanley Cup Playoffs in the bubble). Moreover, they missed the postseason entirely three years in a row (2023, 2024, and 2025).
Pittsburgh’s 2025–26 NHL season was an anomaly. Against all odds, the Pens made the playoffs in Dan Muse’s first year as head coach. However, at the end of the day, it was only an oasis in the desert. It takes no master in biology to know a penguin won’t last long in the desert, and thus time is running out for Pittsburgh to figure out what’s wrong.
It starts with Malkin
Nailing the Malkin decision in the offseason is only the first step, yet it could well make or break Dubas’ plans for the summer. Crosby has sent his two cents out there for the organization to listen to, and it will. However, Crosby is only signed through one more season, and sooner or later, the Penguins will have to brace for a team that no longer features “Sid the Kid.”
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