Sidney Crosby keeps getting pulled back into the same rumor cycle, and the Montreal Canadiens are right there with him.
The latest chatter has the Crosby-to-Montreal connection resurfacing, but the line from the reporting is pretty clear: there’s not much substance to it right now. Crosby already shut down trade noise once by signing a two-year extension and reaffirming his commitment to the Penguins, and the current round of speculation feels like a rerun. He is due for another extension now, and once again the conversation has started to spin.
The Canadiens link makes easy sense on paper. Crosby grew up as a fan of the team, played his junior hockey with the Rimouski Oceanic, and Montreal is the closest NHL club to his Nova Scotia home.
The fit is obvious, too, since the Canadiens need a second-line center and are trying to push toward contention. Still, the reporting points back to Pittsburgh.
Josh Yohe of The Athletic wrote that extension talks are expected to ramp up at the end of the summer before the season begins, and that a one- or two-year deal would fit the situation. Crosby’s last contract was signed in the middle of September, so that timing would line up again.
For now, the read is that Crosby will finish his career with the Penguins.
One of the more colorful takes came from The Sid Seixeiro Show, where Seixeiro said, “I’ll believe it when I see it”, when discussing a Crosby extension. He also floated Michael Hage and a first-round pick as the kind of trade package that could be involved if Montreal ever tried to chase the idea.
Connor Hellebuyck’s future in Winnipeg is another situation that has not settled into a clear answer yet. Even deep into the offseason, there is surprise that he is still a Jet at this stage, though there is still plenty of time for something to happen if the team decides to move him. The real issue is whether Winnipeg gets the kind of offer it wants.
There is a belief that owner Mark Chipman and Kevin Cheveldayoff want to get a deal done, but Hellebuyck’s own wishes are less clear. What does seem obvious is that contending matters to him.
Adam Lowry told Murat Ates of The Athletic, “…Until something happens, he’s a Jet, he’s a good friend, and we’re excited to get him back.” Ates also noted that Lowry does not appear to have any special insight into the trade talks or the broader situation.
The Buffalo Sabres are still the team many expect to be in the mix if Hellebuyck is moved, but there is no information on whether he has a short list of destinations. Other teams could also jump in with a major offer.
Hellebuyck has a no-move clause for the 2026-27 season, which becomes a 21-team no-trade list next offseason. Winnipeg could keep him now and still create some flexibility later if he remains unwilling to stay.
Back in Montreal, the defense picture is crowded enough that a trade somewhere in that group is starting to make sense. Lane Hutson, Mike Matheson, Noah Dobson, and Kaiden Guhle headline a blue line that already looks strong, but there are only so many full-time spots to go around.
Arber Xhekaj has built his identity around being a physical presence, though he still does not have a contract and has been in trade talk all offseason as a restricted free agent. Alexandre Carrier logged heavy minutes late last season and through the playoffs, so he appears safe. Beyond that, Adam Engstrom, Jayden Struble, and David Reinbacher are all part of the conversation.
The real battle is for the bottom-pair jobs, and the Canadiens have some choices to make. Apron Basu addressed that group in a recent Athletic mailbag and said Engstrom has been dangled as a trade chip, but also that Montreal values him highly and is trying to use him, or another defenseman, to help upgrade the forward group.
In Other News...
Canadiens Still Have One Roster Question Around Xhekaj And Bolduc
Geoff Molson sounded upbeat in a recent interview about where the Canadiens stand after last season, saying he was satisfied with the teams performance and encouraged by the way the roster is developing. He also made clear that Arber Xhekaj and Zach Bolduc remain important pieces in the organizations plans, a notable point with training camp approaching and Montreal still sorting through the edges of its depth chart.
The bigger question is how both players fit once the dust settles. Xhekajs usage has not fully settled into a defined role, and Bolduc remains unsigned after finishing the playoffs on the fourth line, leaving Montreal with one of those familiar late-summer roster puzzles that can shape how a team starts the year. [Read more 🡒]
Canadiens Roster Puzzle Puts Some Young Pieces In Play
The Canadiens search for help on the right side of their defense has turned into a roster puzzle with real long-term stakes. With future salary-cap room to work with, the front office can afford to think beyond a quick fix, and that has kept attention on a possible move for Zach Whitecloud as Montreal looks to balance its blue line while also adding more size and physicality up front.
What makes the conversation more interesting is the kind of young talent that could be pulled into the discussion if the Canadiens decide to press ahead. Montreal has prospects it would prefer not to move lightly, but it also has to weigh the value of future flexibility against the appeal of helping the current roster now. For the moment, it is still speculation and planning more than action, but the kind of move the Canadiens are considering could reshape more than one part of the lineup. [Read more 🡒]
Canadiens May Go Only As Far As Ivan Demidov Takes Them
Montreal did not make many sweeping changes this offseason, choosing instead to tinker around the edges while letting the roster largely carry over. The most notable departures were Brendan Gallagher and Joe Veleno, and the additions were mostly depth pieces aimed at the AHL side, which leaves the Canadiens leaning on internal growth more than outside fixes.
Ivan Demidov is at the center of that bet after a rookie season that put him firmly on the leagues radar and left him second in Calder Trophy voting. He showed plenty of upside, but he also cooled late, and Montreals outlook now hinges on whether he can turn that promise into steadier second-year production. For a team that did not do much to change its ceiling, his next step may end up setting the tone. [Read more 🡒]