The future of Sidney Crosby has once again become one of the NHL’s most-discussed topics. The Pittsburgh Penguins captain, now 38, remains one of the league’s most respected players. Still, with his contract running through 2027 and the team struggling to stay competitive, questions about how his story in Pittsburgh will end and whether it could include a move to another team are resurfacing.
Could Sidney Crosby’s Next Chapter Begin in Montreal?
On the Flamesnation show Barn Burner, TSN insider Darren Dreger added fresh momentum to the conversation. Dreger suggested that a “win-win” scenario could emerge if the Penguins and Crosby eventually part ways.
“As much as Sid loves the romantic idea of staying with the same organization the entire year, there’s something noteworthy and sweet about giving something back to that organization on your way out. Why can’t it be a win-win?,” he said.
He noted that while Crosby has always valued loyalty and legacy, there’s a “sweetness” in giving back to the organization that built his career before moving on.
According to Dreger, with its young talent and deep admiration for Crosby, Montreal would “do whatever is possible” to acquire him if the opportunity arises.
“But Kyle Dubas is looking at what he has to do in terms of the rebuild in Pittsburgh, so I think it’s relevant to have these conversations specific to Sid now. Last year or the year before, I thought it was a tad premature,” he noted.
Trade talk around Crosby isn’t new, but it has intensified following the latest episode of Amazon Prime’s “FACEOFF: Inside the NHL.” In the documentary, Crosby’s longtime agent, Pat Brisson, reportedly avoided addressing that idea.
Filmed during last season’s trade deadline, Brisson admitted that teams have inquired about Crosby’s availability. “People say, ‘Is Sidney going to get traded?’ Teams want to know if there’s a possibility they can get that No. 1 center,” he said.
He also acknowledged that being outside the playoff picture for multiple years “must be hard to see the light at the end of the tunnel.” Those remarks, though not direct trade hints, fueled headlines across the league.
When asked about it himself, Crosby admitted the rumors can’t be ignored during tough stretches. “When you’re losing and not sure where things are going to end up and you hear all the rumors, there’s obviously thoughts that run through your head,” he said.
However, he emphasized that his loyalty remains with Pittsburgh, adding, “You take so much pride in being part of the team and the organization. The people there have been so great to me – that’s difficult to just walk away from.”
Montreal Canadiens Whispers Grow Louder
Montreal continues to surface as the most logical landing spot if Crosby were ever to leave Pittsburgh. The veteran center grew up a Canadiens fan, and his warm reception during the 4 Nations Face-Off at the Bell Centre earlier this year reminded everyone of that long connection.
While Crosby has laughed off the speculation, insiders reportedly believe the Canadiens’ young core and strong future could appeal to him should the Penguins embark on a full rebuild.
General manager Kyle Dubas has downplayed the trade rumors, calling them “a distraction,” and has reaffirmed that Sidney Crosby is central to the team’s plans. Still, sources close to the organization suggest that a full teardown could put pressure on both sides.
Both sides insist their focus remains on returning to contention. But as the team navigates uncertainty, from possible ownership changes to trade chatter, the idea of Crosby in a Canadiens sweater lingers in hockey circles.
