Canadiens Mailbag: What might it take to get Crosby to Montreal?

I received over 90 questions for this mailbag, but none more compelling than this first one.

I like the way Jon’s question is framed. And since Sidney Crosby is le sujet du jour in Montreal, it’s only fitting we start this mailbag here, provided everyone reading this understands we’re just delving into fantasy.

All I’m presenting here is opinion, with no new information to go on and endless assumptions to make.

As far as anyone knows, Crosby wants to be a Pittsburgh Penguin for life, and there are no indications that’s changed.

I’d imagine there’s less than a handful of people who know how he’d truly feel about coming to Montreal, if it were to change. There’s been a lot of speculation the soon-to-be 38-year-old would jump at that opportunity, but it’s all been driven by perception: by Crosby growing up a Canadiens fan, by father Troy being a former draft pick of the franchise, by the idea he’d be compelled by the team’s rise and its promising core, and by Crosby making his love for playing at the Bell Centre well known throughout his 20 years in the NHL.

Even assuming all those factors were relevant enough to Crosby, they might not be relevant enough for him to leave Pittsburgh and choose Montreal over other places.

When I said I liked the framing of Jon’s question, part of the reason was it started with asking about those other places. Without considering the marketplace, it would be impossible to say what it would take for the Canadiens to get him.

It’s hard to project, regardless, because one of many major assumptions I must make to flesh out this exercise is about where else Crosby would want to go.

I’d hardly be putting myself on an island suggesting Colorado would be one destination of choice. With fellow Nova Scotian and good friend Nathan MacKinnon there and the Avalanche already a Cup contender, it’s hard to imagine him preferring another team.

Crosby might like Los Angeles just as much, though.

Like the Canadiens, the Kings may not be as strong as the Avalanche. But that could change with Crosby in the fold, and if he feels that way, I think chasing the Cup from Hollywood and living closer to longtime agent Pat Brisson could prove appealing to him.

One of the biggest assumptions would be that it ends there for Crosby, and that the Vegas Golden Knights and Florida Panthers, who seem to be involved in any and every transaction for a big-time player, wouldn’t be invited in on this one.

Say we make that assumption, and make another huge one that Montreal, Colorado and Los Angeles would be equal destinations of choice for Crosby, the question then becomes: which of the three can best address the Penguins’ needs?

It seems obvious the answer is Montreal.

The Canadiens are flush with high-value picks and quality prospects, and Pittsburgh needs high-value picks and quality prospects more than anything else.

Neither the Avalanche nor Kings have as much to offer if the Penguins go after what they require most.

Colorado depleted its already-shallow pool when it acquired the depth it realized it required to affirm its status as a perennial Cup contender. Moving on from Mikko Rantanen and adding several players was a philosophical shift I can’t see the Avs suddenly reversing — even after losing in the first round to Dallas — but taking on Crosby’s $8.7 million cap hit for the next two seasons would almost certainly force them further back down the road from which they came.

Hey, at least the Avs would get Crosby!

Still, doing so would prohibit them from keeping other key pieces and make it harder for them to pay suitable replacements on the open market. And acquiring the appropriate replacements via trade would prove beyond challenging, too, after spending assets to get Crosby.

We’re not even sure how the Avs would outbid Los Angeles, let alone Montreal, for Crosby without owning a single pick in the first three rounds of the next two drafts.

Maybe they could overcome that by loading the deal with prospects, but there aren’t many — if any — A-level ones left in their pool after giving up Calum Ritchie in the Brock Nelson deadline deal.

The Kings don’t have many top-quality prospects, either. But they do have a first-round pick in each of the next three seasons, and a second in two of them. A combination of stud prospect Liam Greentree and some of those picks would be what they’d have to work with to acquire Crosby.

Yet parting with all that would leave the Kings with barely anything else for future moves they’d want/need to make to bolster their chances while Crosby’s under contract.

Like the Avs, they have compelling, young roster players to consider moving in a Crosby deal.

But that’s not what the Penguins need most in moving Crosby and sparking a series of franchise-altering moves that propel them towards a much brighter future.

Which brings us back to the Canadiens.

They have the 16th and 17th picks in this year’s draft and can part with either one (or both) in a package to acquire Crosby. They could also package one with a lottery-protected first in 2026, and they could even dip into one of their second-round picks — they have two in each of the next two drafts — as a potential sweetener. And they can throw in any combination of two prospects not named Demidov, Reinbacher, Fowler or Hage to complete the deal while taking on Crosby’s full cap hit.

Could the Avs or Kings take all of Crosby’s contract and beat a deal of, for example, 16th overall in 2025, a top-10-protected first in 2026, a second in either year, and Logan Mailloux and Oliver Kapanen (who were, respectively, chosen in the first and second round of the 2021 draft and have already gotten their feet wet in the NHL)?

It would take some tremendous creativity, and a lot of other manoeuvring, but it feels like too much for Colorado and Los Angeles.

Some might look at it and say it’s too little for Pittsburgh, but it would be a huge haul considering the marketplace, and that Rantanen — who’s 10 years younger than Crosby, slightly more productive over the last three seasons combined, and signed for six more seasons — went from Carolina to Dallas for two firsts, two thirds and Logan Stankoven at the deadline.

Accepting what I proposed from Montreal would leave the Penguins with three firsts in this year’s draft, two in next year’s and five second-round picks spread over both, while netting them two quality, NHL-ready prospects under the age of 23. They can tweak it however they like — maybe they’d prefer to have Adam Engstrom added to Mailloux, or Owen Beck over Kapanen, or firsts in 2026 and 2027 because they already have two in 2025 — but it’s the type of deal they should look to make if Crosby requests to leave.

He may never, though. And so long as it appears like he won’t, there’s far too much unknown to accurately pinpoint what the marketplace for him might be and what it might take to get him to Montreal.

The logical answer is yes, but that’s purely based on what Dach looked like at centre this season — coming off a training regimen that didn’t adequately prepare him to overcome the adversity of returning from torn anterior and medial collateral ligaments in his right knee.

Before those injuries were suffered in fall 2023, we all saw what Dach could do in the middle of the ice, and it was compelling enough to believe he’d be the perfect no. 2 centre for the Canadiens.

But after suffering another long-term injury to that same knee this past February, the 24-year-old would be at a deficit to prove that would be the ideal place for him on next season’s roster.

And even if Jeff Gorton said at this season’s closing press conference “there’s certainly a place for him” in Montreal’s lineup and that it was “going to be up to him where that’s going to be,” we don’t see executive vice-president of hockey operations and general manager Kent Hughes leaving second-line centre up for grabs to a player — or players — who only might be able to fulfil the requirements.

Realistically, Dach can absolutely be a good second-line winger. And playing there probably would provide him the best path to success with the Canadiens.

With success would come confidence, and with confidence Dach might be able to eventually return to centre — if need be, if injury strikes at the position — and deliver on the promise he once showed.

“He has size, he’s competitive, he’s got skill, he’s a very talented player,” said Gorton of the six-foot-four, 221-pounder who was chosen third overall in the 2019 Draft to be a top centre for the Chicago Blackhawks.

Dach’s opportunity to prove he can be one for the Canadiens is on the shelf for now.

He needs to first prove he can be a productive, responsible and consistent player. And the clock is ticking for him to do it, with his contract expiring at the end of next season.

“He’s gonna need a big camp to get himself going and get started early,” said Gorton.

If Dach doesn’t, it could lead to the end of his road with the Canadiens.

I don’t think the door is slammed shut to either of them, but it’s not exactly wide open either.

With the way Dvorak played for most this season — and against the Capitals in the playoffs — I can’t help but think he’s priced himself out of Montreal. The Canadiens already gave 28-year-old Jake Evans a four-year, $11.4 million contract, and it’s unimaginable they’d go as deep with the 29-year-old Dvorak, who will probably do better than that on the open market.

With Kapanen, Beck and Hage in the system and Evans signed, giving Dvorak term doesn’t really work for the Canadiens, and it’s hard to imagine him turning away term to remain in Montreal.

Armia might be willing to accept a one-year deal to stay, but he’d probably have to take a pay cut from the $3.8 million he earned this past season.

And even if the Canadiens might offer the 31-year-old that opportunity, it’s hard to imagine them prioritizing his dossier over others in the coming weeks.

I don’t know about “out of camp,” but let’s use your categories to identify players making the leap at some point next season.

Almost definitely (with staying power): Kapanen, Reinbacher, Mailloux.

Probably (for at least some games): Florian Xhekaj, Joshua Roy, Luke Tuch, Beck.

Could surprise everyone: Jared Davidson.

Every time I watch this player, I see a future NHLer.

I felt that way before this season, with Davidson seemingly always arriving in the right place at the right time. But after watching him play in the hard areas and compete with edge and a willingness to stand up for himself and his teammates in Laval, I feel even more strongly about it.

The 22-year-old had 24 goals and 21 assists in his second pro season, and I wouldn’t sleep on him as a potential breakthrough candidate in his third.

I don’t.

But the Canadiens obviously want to keep that door open, in the event a top-six winger becomes more attainable than a second-line centre.

Gorton made that clear.

“There’s other ways of improving your skill level in your top six,” he said. “I think if you look around the league, there are teams that have players that aren’t necessarily centres that are 100-point players that are driving lines and being very creative players. There’s more than one way to do this.”

I think the Canadiens must at least set the bar there, even if they know hard it is to clear.

The most important thing is they continue to progress, and you don’t progress by lowering your expectations.

Whether the Canadiens can meet elevated expectations is a reasonable question. They have a lot of work to do to give themselves their best chance, and getting it done still might not be enough to keep every team around them gunning for their spot at bay.

The Canadiens are going to improve on paper.

But the NHL is arguably more balanced than it’s ever been, and being better on paper has never meant less.

Still, that shouldn’t preclude the Canadiens from expecting to build on this season’s result.

I received a lot of questions on this subject — most of them asking if Jacob Fowler would be backing up Sam Montembeault in Montreal — and chose this one for a general outlook on the position.

I expect Montembeault to be the starter, I expect Jakub Dobes to be the backup, and I expect the split of games between them will depend entirely on their performance.

As for Fowler, I expect he’ll be starting in Laval, and that the Canadiens will sign a veteran goaltender to help him there.

I wouldn’t expect that goaltender to be Cayden Primeau, even if the 25-year-old’s rights still belong to the Canadiens.

More from Sportsnet

Canadiens must be mindful of balance to keep progressing

How Josh Anderson helped drive culture propelling Canadiens through next phase