Canadiens 5 Moves Away from 2025 Stanley Cup

Considering how close the Montreal Canadiens came to winning the Stanley Cup last summer, is it impossible for them to go all the way three short seasons from now in 2025? In a word, no. However, it’s somewhat a longer answer as to just how they’ll manage the feat. Not one, but five steps, to be exact.

Morning Skate newsletter Click To Subscribe

Remember, the Canadiens rebounded the following seasons after finishing in 28th place both in 2012 and 2018. In fact, they reached the Final in 2021, three seasons after 2018. So, it is at the very least possible.

No one said it would be easy, though. After all, each of the below five steps, which could realistically get the Canadiens back to being a contender, get harder and harder. Coincidentally, they’re also in theoretical chronological order, starting with Step 1:

1. Trade Ben Chiarot and Co.

Obviously, the Canadiens can stand to trade far more assets than just defenseman Ben Chiarot at the upcoming trade deadline on March 21. However, he’s the likeliest player to be moved and fetch a sizable return in the process. As a pending unrestricted free agent, Chiarot’s unlikely to re-sign and see this thing through.

Ben Chiarot Montreal Canadiens
Montreal Canadiens defenseman Ben Chiarot – (Jess Starr/The Hockey Writers)

In his defense, few in his position would considering he’ll likely have his choice of suitors after he led the Habs in ice time last playoffs. Why stick around with the Habs after literally one of the worst seasons in Canadiens history?

Chiarot also represents the old guard in the form of a shutdown defenseman, with general manager Kent Hughes having gone on record saying the Habs would ideally be an offensive-minded team under his watch. So, trading Chiarot for as much as you can get is the logical first step here to future success.

2. Replace Trevor Timmins

With Martin St. Louis shockingly taking over for ex-head coach Dominique Ducharme, that really leaves ex-assistant GM Trevor Timmins as the most significant former executive who must still be replaced.

Trevor Timmins Montreal Canadiens
Ex-Montreal Canadiens assistant general manager Trevor Timmins – (Amy Irvin / The Hockey Writers)

Martin Lapointe is reportedly handling the ex-assistant GM’s scouting responsibilities in the interim. However, it stands to reason, if Hughes/ executive vice president Jeff Gorton have gone to the trouble of inserting their guy as head coach, going way off the board in the process (while also going back on their word), they’ll want the right person (in their minds) overseeing the 2022 NHL Entry Draft too. It’s that pivotal of a event to the future of the organization.

So, rumors that St. Louis’ ex-teammate (and Hughes’ ex-client), Vincent Lecavalier is in line for the position? Somewhat perplexing, admittedly. However, it remains unclear how much of Timmins’ old role he’ll fill. As ex-GM Marc Bergevin has effectively been replaced by two men, perhaps the Habs will go the same route with Timmins.

3. Draft Shane Wright

Now, there’s some room to maneuver here, in the sense that it’s far from top-prospect Shane Wright or bust. However, drafting Wright would solve a lot of problems the Habs have (which is saying a lot). Even if he’s not a generational talent, the projected No. 1 overall pick does fit the mold of a two-way, top-six center at least, one who models his game after that of Patrice Bergeron for what it’s worth.

Related: 2022 NHL Entry Draft: Baracchini’s Mock Draft 1.0

So, why Wright? Other than him being the best player available next summer? While the Canadiens are relatively deep on the wings (when healthy), they absolutely need the depth down the middle, having lost Phillip Danault and Jesperi Kotkaniemi last summer. If the Canadiens draft Wright (or Logan Cooley for another example), they’d go a long way to setting themselves up for future success.

Shane Wright Kingston Frontenacs
Kingston Frontenacs forward Shane Wright – (Photo by Robert Lefebvre/OHL Images)

It should be noted the Canadiens’ defense is in an arguably greater state of disrepair, but, if we’re sticking to a three-year window, forwards do tend to develop faster than defensemen. Addressing the defense will have to be done some other way…

4. Sign Brett Pesce to Long-Term Deal in 2024

There’s a hope the Canadiens’ top defensive prospects will bridge the gap between now and 2025, filling massive holes on the blue line in the process. So, we’re talking the likes of Kaiden Guhle, Mattias Norlinder, Jordan Harris (if he signs) and even Alexander Romanov, who’s already made inroads towards becoming a fixture on this team’s defense for years to come.

There’s one thing all four of those prospects have in common, though: They’re all primarily left-side defensemen, leaving the right side relatively bare, especially if the Canadiens trade Jeff Petry, as is rumored to happen. Of course, even if they didn’t, Petry would be 37 by the time 2025 rolls around. He’d need to be replaced to some extent anyway, even if he’d still be under contract by then.

Jeff Petry Montreal Canadiens
Montreal Canadiens defenseman Jeff Petry – (Jess Starr/The Hockey Writers)

The Canadiens could theoretically trade for a defenseman, but it’s hard to predict who’d be available between now and then. You’d have to look at pending unrestricted free agents for 2022, 2023 and 2024 for an idea. For example, Dallas Stars defenseman John Klingberg is the prototypical puck-moving defenseman the Canadiens should go after, but he’s going on 29 now with his deal expiring this coming summer. In 2025, he’ll be going on 32.

That’s not necessarily a dealbreaker, as Petry was an effective co-No. 1 defenseman up until age 33. However, Petry’s also the exception and not the rule. For a signing to work out and line up with the predefined three-season window, you’d have to time it better. Players like Matt Dumba (2023) could be interesting, but he doesn’t encapsulate an in-his-prime Petry’s all-around ability as much as the Habs would likely like. The next free-agent class, in 2024, is where the real focus should be.

Noah Hanifin of the Calgary Flames and Devon Toews of the Colorado Avalanche will each be unrestricted free agents heading into the 2024-25 season. However, even though each should fetch a king’s ransom (assuming they aren’t locked up long term by their respective teams by then), they’re both left-handed shots. Even so, the true prize would be Carolina Hurricanes d-man Brett Pesce, who will be a respectable 30 years old at that point. Signing him to a long-term deal would still be the only realistic way to get him under contract (at least the most realistic way). It could still work out, though.

Brett Pesce, Carolina Hurricanes
Carolina Hurricanes defenseman Brett Pesce – (Amy Irvin / The Hockey Writers)

One of the league’s truly underrated defensemen, Pesce is a defensive stalwart who can chip in offensively, maybe not to the same degree Petry was expected to this season. For a team that’s presumably looking to get more mobile, but stay solid defensively, there should still be no doubt: Pesce is the guy. Plus the theoretical opportunity to cherry-pick him away from the Carolina Hurricanes? Gravy.

5. Assess Carey Price’s Play and Potentially Replace Him

Carey Price’s Conn Smythe Trophy-caliber performance last playoffs (at least up until Round 4) went a long way, silencing his critics. He won the first third-round game of his career, one-upping himself with a single Stanley Cup Final victory to boot. So, he clearly has the potential to carry a team on his back in the playoffs.

Sign up for our regular 'Habs Newsletter' for all the latest.

The question lies in whether or not Price will be able to do so again three years from now, at which point he’ll be on the verge of turning 38. That means he’d be older than Tim Thomas (37 with the Boston Bruins in 2011) and Dominik Hasek (37 with the Detroit Red Wings in 2002) when they each won. No one else this century comes close. Even Canadiens great Patrick Roy was “just” 35 when he won with the Colorado Avalanche in 2001.

So, even though Price at one point was the best goalie in the world and reminded everyone last summer that he’s still got something left in the tank, there should be real concerns as to whether or not the tank will last another three years.

Carey Price
Montreal Canadiens goaltender Carey Price – (THE CANADIAN PRESS/Ryan Remiorz)

It should be noted Cayden Primeau, the team’s goaltender of the future for all intents and purposes, will be 25 going on 26 at that point in time, which would line up fairly well. However, Primeau’s development has taken a step back this season, arguably through little fault of his own.

If Primeau isn’t the guy, thankfully the Canadiens have a few options via free agency in 2024: Former Vezina Trophy-winner Connor Hellebuyck and upstart New York Islanders netminder Ilya Sorokin. Of the two, Sorokin may be the better bet, as he’ll be just 29 at the time (compared to Hellebuyck at 31).

However, as nice and good as all that is in principle, there’s one major sticking point preventing such a fantasy from coming to pass. Price is under contract, with a cap hit of $10.5 million until 2026. He would have been hard to move, if he were healthy, this season, with the Seattle Kraken infamously passing on the opportunity to take on his contract for free. He’ll be near-impossible to move in three years, ironically making the one player, who had the most to do with getting the Habs as far as they did last summer, the biggest obstacle to them getting there again in 2025.

A lot can of course happen in three years, to the point that breaking it down into five moves seems ludicrous. Ironically again though, in Price’s specific case the hope is very little at all changes. To be clear, these are just the overarching moves that would set the tone and build the foundation of a winner. Rest assured, the Canadiens will be defined by many more than just five moves between now and 2025, but, if the right moves are made, a Stanley Cup is far from outside the realm of possibilities.