Canadiens Suddenly Have A Bigger Trade Question Hanging Over Them

As trade talks swirl, speculation mounts on Connor Hellebuyck's future with the Winnipeg Jets, while the Detroit Red Wings set a high price for Dylan Larkin.

Chris Tanev’s status has shifted from cautious optimism to week-to-week, and the Maple Leafs are now bracing for a longer wait than they expected.

TSN Hockey Insider Darren Dreger said Toronto first believed the defenceman might not miss much time, but that changed after the team brought him back to Toronto and ran additional tests. The new timeline came after earlier information left the Leafs feeling upbeat about the injury.

“Week-to-week means that’s the time required to get Tanev healthy and back on the ice.”

Dreger also urged Leafs fans not to jump straight to worst-case thinking, pointing to the injury Tanev dealt with last year as part of that reassurance.

Elsewhere, the Connor Hellebuyck situation remains stuck in place, even if the speculation around him is not. Dreger said the Winnipeg Jets goalie has already lost more than $600,000 while sitting at home and waiting on a trade, but that the real focus remains the same: moving him for a fair return.

What Dreger is hearing is that Winnipeg general manager Kevin Cheveldayoff has been patient through months of talks, offers and interest from what he described as tire kickers, but nobody has stepped up with the right deal yet. And as for the idea of Hellebuyck ending his holdout and returning to the Jets while he waits, Dreger didn’t buy it.

“Nothing has changed on that front, and I do not expect to see Hellebuyck back with the Jets.”

In Detroit, Shawn Horcoff’s first big swing as interim general manager came with Alex DeBrincat, who agreed to a new seven-year, $91 million contract. But that hasn’t solved everything for the Red Wings, with restricted free agent Simon Edvinsson still unsigned and no deal yet involving Dylan Larkin.

Dreger said the price on Larkin is exactly the kind of haul you’d expect for a player of his stature: three or four pieces, including two “A”-quality prospects, a top-nine forward, and a first-round pick. He also noted that Larkin’s contract runs through 2031 with an $8.7 million cap hit, and that plenty of teams would want him if he were available to everyone.

The catch, Dreger said, is that those teams are not on Larkin’s trade list.

“So far, there hasn’t been a fit - at least with the teams on his list.”

Montreal’s Josh Anderson is also drawing attention after piling up goals early, including two in the Canadiens’ game against the Washington Capitals. That gives him four goals in seven games, a strong start for a 32-year-old winger in the final season of his seven-year deal.

Dreger said the Canadiens’ goal is to extend Anderson, while also acknowledging the reality of how his camp operates. Anderson is represented by Darren Ferris, who Dreger said often pushes clients toward July 1 to test the market. Even so, Dreger added that Anderson and his family like staying in Montreal, and that he has already had success there.

He also said Kent Hughes spoke with Anderson before the season and told him the Canadiens were focused on trade and trying to add pieces to help the team, asking for a little more time before turning to Anderson’s situation.

Then there’s Rick Bowness, who was blunt again with his team. Dreger said the Columbus coach’s latest comments about effort fit a pattern, not an isolated outburst, and pointed back to similar moments at the end of last season. The concern, he said, is that repeated public criticism can turn into a problem if the room starts to slip.

That, Dreger said, can’t happen in Columbus.

In Other News...

Cole Caufield Gives Canadiens Fans Another Officiating Debate

Cole Caufield has already given Canadiens fans plenty to watch early this season, but his latest moment came after the whistle rather than in the attacking zone. During Montreals game against Washington, the winger spoke to a referee after being assessed a penalty, turning a routine stoppage into another flashpoint for a fan base that never needs much prompting when the officiating feels uneven.

The exchange fit a familiar frustration around the Canadiens, especially in tight games where calls can seem to swing with the score and the moment. Matt Drake noted that this kind of play is often not ruled consistently, and Caufield has still been productive with three goals and four points in six games, but the real conversation may linger longer than the penalty itself. [Read more 🡒]

Canadiens Suddenly Have A Third-Period Problem They Can't Ignore

The Canadiens had enough early offense to make it feel like they were in control, with Josh Anderson scoring twice and giving Montreal a quick cushion against Washington. But the 5-4 loss kept fitting an increasingly uncomfortable pattern for this group, one that has little to do with a lack of compete and everything to do with how games are slipping away late.

Montreal has been leaning on its openings more than its finishes, and the third period has already become a problem worth watching through the first seven games. The Capitals game added to the concern, with Jakub Dobes coming back into the crease after more than a week and the Canadiens again unable to protect a lead or close the door when the pace tightened. [Read more 🡒]

Red Wings Suddenly Face Two Roster Questions They Can't Ignore

The rumor mill around the Red Wings has picked up speed, and Montreal is right in the middle of it. The Canadiens are being linked to captain Dylan Larkin, a target that would instantly change the shape of their forward group if Detroit were willing to listen, while the rest of the league waits for bigger names and broader trade markets to develop. Even with Toronto nursing a week-to-week injury on defense and Los Angeles kicking around a Connor Hellebuyck idea, this remains the kind of story that can keep a front offices phone line busy.

For Montreal, the appeal is obvious: a chance to chase a proven top-line center if the situation ever lines up. For Detroit, the complication is just as clear, because Larkins destination preferences matter here, and the Canadiens are not currently among the teams that fit neatly into that picture. At the same time, the Red Wings have another contractual issue brewing with defenseman Simon Edvinsson, which only adds to the sense that Detroit has multiple pressure points to manage before anything on the roster front becomes simple. [Read more 🡒]