Sidney Crosby and the Pittsburgh Penguins have very different timelines, and it could lead to the end of the 20-year relationship. A report around the NHL hints the captain’s patience might be reaching a tipping point.
It’s impossible to imagine Crosby in any uniform other than the Black and Yellow. However, the day might actually arrive. Perhaps not this season, but if there’s ever been a moment when Crosby has considered leaving the Penguins the most, this is it.
“I never thought a Crosby trade was imaginable. Now, I’m not so sure. If Brisson is indeed speaking for his client, then there is reason to believe that Crosby’s frustration with the current state of the Penguins is at a boiling point,” The Athletic’s Josh Yohe stated.
‘Hab’ it your way
The Penguins can’t really sleep well at night knowing there’s a scenario in which Crosby exits the organization. The rest of the NHL is keeping an eye open in case the Pens’ captain actually asks for a trade.
Sidney Crosby at Heinz Field on February 25, 2017 in Pittsburgh, Pennsylvania.
However, there is one franchise that seems to be in pole position if the race for Crosby ever hears the starting gun. It’s difficult to see a path in which Crosby asks out of Pittsburgh and Montreal isn’t there to pounce on the three-time Stanley Cup champion. As reported, the Habs might already be planning for the future with Crosby, even if that future never pans out.
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“[Canadiens’] Jeff Gorton and Kent Hughes are they sitting there and saying ‘we’re not doing anything with X player because we think it may prevent us from doing a Crosby deal‘,” insider Elliotte Friedman stated on the 32 Thoughts Podcast.
More ways than one
Right now, the Canadiens’ roster looks like a complete opposite to the one in Pittsburgh. The Penguins feature aging players while the Habs’ are only entering their best years in the NHL. A trade to Montreal wouldn’t only fulfill Crosby’s childhood dream, but it would place him in prime position to chase a fourth Stanley Cup in his career.
Sidney Crosby during Hockey Canada’s 2025 National Teams Orientation Camp.
The Canadiens were clearly missing experience and depth last season, as the Washington Capitals knocked them out in the first round of the Stanley Cup Playoffs. The only way to gain seasoning is through hardships and being put in challenging situations. There is another way, though, and trading for Crosby would provide precisely that.
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Thinking it through—and thoroughly
In more ways than one, it seems a win-win situation for Sid the Kid and Montreal. The real loser? The Pens, and as a result that might drive Crosby to steer away from a trade request. As much as it stings to languish at the bottom of the standings, Crosby has no desire to hurt the organization in The Burgh. Regardless, at some point it will come down to a crude dilemma: him or them. And as a 38-year-old chasing silverware, Crosby may be left with no other choice.
A move before or during the 2025-26 NHL season seems unlikely. After all, Crosby wants to play alongside Evgeni Malkin in the latter’s final year in The Burgh. Moreover, a change of scenery to a market like Montreal could prove too distracting for Crosby, whose main goal this season is to be at his best for the 2026 Olympics in February.
SurveyIf Crosby asks for a trade out of Pittsburgh, does it change how Penguins fans see him?
If Crosby asks for a trade out of Pittsburgh, does it change how Penguins fans see him?
Needless to say, asking for a trade is a serious decision that requires careful thought and time. Crosby won’t act on impulse whatsoever. He knows, as well as anyone else, that once he makes his pitch to the brass in the City of Bridges to ship him away, there will be no turning back, and the NHL landscape would change forever.