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Kiefer Sherwood has 12 goals this season and over the last three seasons leads the league in hits with 794 in 169 games. Could he be a trade fit for Montreal? Minas Panagiotakis / Getty Images
In the Montreal Canadiens’ continued pursuit to scour the trade market and get better, there has been a concerted effort to avoid situations where they feel forced to do something, to overpay for a short-term fix.
It is a prudent approach, especially when the Canadiens don’t feel they are one move away from Stanley Cup contention, which is the ultimate goal.
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At the pre-season golf tournament, president of hockey operations Jeff Gorton made a point of stating that the Canadiens have reached a point where they can afford to be “picky” with their next move. That was an acknowledgment that the Canadiens had already spent a good amount of trade capital in acquiring Noah Dobson and Zack Bolduc in the offseason, but also that they would need to be very specific in terms of the player profile they go after next.
A second-line centre was the Canadiens’ priority over the offseason, and it remains so today. It does not require much hockey acumen to look at the Canadiens’ depth chart and understand that is an organizational need.
But the Dobson trade was informative in terms of how this administration thinks, because while a top-pair, right-shot defenceman was a need, it wasn’t an obvious need. This administration drafted David Reinbacher with the No. 5 pick in 2023 in the hopes he would one day become a Dobson-like player, a right-shot puck-mover with length and defensive smarts.
However, despite having Reinbacher in the system, when the actual Dobson became available on the trade market, the Canadiens did what was necessary and paid a high price to acquire him.
Fast-forward to last Friday when Gorton was a guest on Overdrive on TSN 1050 ahead of the Canadiens facing the Toronto Maple Leafs on Saturday night. It was one day after Washington Capitals forward Tom Wilson had taken out Jake Evans with a high hit moments before the Capitals scored, an eerily reminiscent moment to last season’s playoffs when Wilson did the same thing to Alexandre Carrier in Game 4 just before the Capitals scored a dagger goal in that game, a turning point in the series.
Gorton, when asked by Frankie Corrado if Wilson represents a player profile he feels the Canadiens lack, did not deny the desire to add that element to his team.
“He’s figured out what the line is, better than others.”
Jeff Gorton on Tom Wilson’s hit on Jake Evans and his physicality on the ice.#GoHabsGo pic.twitter.com/mjHcortIGy
— OverDrive (@OverDrive1050) November 21, 2025
“Yeah, without question,” Gorton responded. “I think all 32 teams would welcome a guy that can skate and has that kind of impact every night. We’re not naive to it, we’re all looking for players like that, but they are harder and harder to find. When you get them, you hold on to them like Washington has.”
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That was Friday.
On Monday, Gorton and/or Canadiens general manager Kent Hughes got a ping in their inbox stating that the Vancouver Canucks are open to listening on any of their impending unrestricted free agents.
Colleague Thomas Drance had a very good and informed breakdown of the situation for the Canucks on Tuesday morning, and noted that the conversation for Kiefer Sherwood would start with a second-round draft pick.
As Corrado noted in that interview Friday with Gorton, there is only one Tom Wilson in the NHL. But if you are looking for a Tom Wilson proxy, you could do far worse than Sherwood. He has 12 goals this season and over the last three seasons leads the league in hits with 794 in 169 games.
The Canadiens, it should be noted, have two second-round picks in the 2026 draft, their own and Columbus’ thanks to the Patrik Laine trade.
Much like the Dobson situation, this seems like a situation that pops up and meets a need that might not have been a priority before, but one where the opportunity supersedes whatever plan existed prior.
The ability to sign Sherwood to a reasonable contract extension would go a very long way in determining the price the Canadiens would hypothetically be willing to pay for a player who scored a career-high 19 goals last season at age 29, and is trending toward a new career high this season at age 30.
But more important than the contract is the calculation of opportunity cost versus the long-term view the Canadiens have tried to prioritize up until now.
Basically, is this an opportunity that warrants the Canadiens playing the “picky” card?
The NHL trade market is essentially frozen, the Canucks’ memo sent out Monday was one of the first indications of a thaw, and there happens to be a player available that suits what the Canadiens need right now.
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There is, however, a prudent way of looking at this. The extra second-round pick the Canadiens shrewdly collected through the Laine trade could be used for something that suits their long-term needs even better than Sherwood. Or the extra fourth-round pick they have thanks to the Johnathan Kovacevic trade could be used to acquire someone like Teddy Blueger, who is another Canucks impending free agent that would help the Canadiens’ penalty kill and is excellent on faceoffs from the left side. Or it could be used to acquire someone else.
This is the last year the Canadiens have extra draft picks. Hence the need to be picky.
But one thing about Canucks president of hockey operations Jim Rutherford is he has a tendency to act long before the trade deadline, and the fact the Canucks sent out that memo Monday suggests he is ready to act quickly again in this instance.
Last season right around this time, the Canadiens pounced when they had a clear need on defence and acquired Carrier from the Nashville Predators for Justin Barron, a valuable trade chip for them. That trade helped turn their season around.
If a second-round pick is what it would take to pry Sherwood out of Vancouver, and it might take more than that, the Canadiens need to view this as an opportunity similar to the Carrier situation a year ago.
It’s true that Carrier was under contract and Sherwood is an impending free agent. But it is also true that Sherwood is a rare commodity the Canadiens need and they have the ammunition to get him.
That ammunition, however, is precious. Could that extra second-round pick in the Canadiens’ arsenal be enough to eventually land Ryan O’Reilly out of Nashville? Perhaps? And would O’Reilly better fill what the Canadiens need, especially since he has another year left on his contract?
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This is the tricky balance the Canadiens have this season, one in which they are not necessarily ready to truly contend, one in which they have a dwindling number of trade assets, and one in which they cannot spend those assets frivolously, especially to acquire a player who could walk away for nothing at the end of the season.
But as Gorton said, players like Sherwood have become harder and harder to find, and the Canadiens would have until July 1 to re-sign him if he proves worthy.
There is a reason why this stage of a rebuild, where a team attempts to transition from promise to contention, is considered the most difficult. It is because of decisions like this where future plans are derailed by current opportunities.
This is where the Canadiens find themselves. You can only be picky for so long.
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Arpon Basu has been the editor-in-chief of The Athletic Montréal since 2017. Previously, he worked for the NHL for six years as managing editor of LNH.com and a contributing writer on NHL.com. Follow Arpon on Twitter @ArponBasu
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