Which Canadian NHL Teams Are Closest to Winning the Cup After the Start of Free Agency?

Adam Proteau ranks the Canadian NHL teams after the beginning of the off-season based how likely he thinks they are to win a Stanley Cup, with a close decision at the top.

After a whirlwind day of spending on the free agent market, the NHL’s 32 teams have shifted expectations on them for the 2024-25 season. But what happened to the league’s seven Canadian teams? And more specifically, which teams got closer to winning a Stanley Cup? 

Here's this writer's list, in order of most likely to win it all to least likely:

The Canucks were rumored to be in on elite UFA winger Jake Guentzel as their primary free agent target. But although Guentzel wound up in Tampa Bay, Vancouver GM Patrik Allvin did what he could to solidify his team’s grasp on top spot in the Pacific Division. 

Keeping support players Tyler Myers, Teddy Blueger and Dakota Joshua was important for the Canucks’ depth, but Allvin upped the ante by using his cap space to acquire UFAs Jake DeBrusk, Danton Heinen, Kiefer Sherwood and Vincent Desharnais. The end result is a Vancouver team that looks at least as strong as it was last season, with a strong goalie in net, an elite top defenseman and great set forwards. It's very close, but Vancouver could probably be the best chance Canada will have at a Cup next season.

After finishing one win short of a Cup this past season, the Oilers needed to make only a few tweaks to their roster. Oilers CEO of hockey operations Jeff Jackson and his management team used their limited cap space to bring back veterans, including Connor Brown, Corey Perry, Adam Henrique and Calvin Pickard. 

As far as Oilers newcomers go, the organization signed forwards Viktor Arvidsson and Jeff Skinner, which will help Edmonton’s secondary scoring and, for Arvidsson, add some more sandpaper to the lineup. 

All things considered, the Oilers will once again be a Cup favorite. While they have more high-end talent than the Canucks, Edmonton will be hard-pressed to take that final competitive step and win their first Cup in 35 years.

The Maple Leafs were one of the more active teams on the first day of free agency, signing veterans Chris Tanev, Oliver Ekman-Larsson, Anthony Stolarz and Jani Hakanpaa to multi-year contracts. 

That said, there was a sense Toronto GM Brad Treliving wasn’t done Monday, and potential trades – possibly including David Kampf or Nick Robertson – could further alter the Leafs’ lineup. 

The Leafs improved their all-around attack, and while there will be intense pressure to produce better results, on paper, Treliving did what was asked of him. Toronto will be a playoff team once again in the difficult Atlantic Division, but we all know the Maple Leafs will ultimately be judged by their playoff success.

This writer has not been especially high on the Jets in recent years. Considering Winnipeg has been unable to get out of the first round of the playoffs for the past two seasons, questions about their trajectory are justified. 

Compounding matters is the Jets’ comparative lack of movement on the first day of free agency, as all that really happened to Winnipeg was the departure of veterans, including defenseman Brenden Dillon and goalie Laurent Brossoit. 

Sure, Jets GM Kevin Cheveldayoff replaced them with D-man Colin Miller and netminder Kaapo Kahkonen, but they hardly seem like an upgrade. 

In a more competitive Central Division, Winnipeg could drop down a spot or two in the standings. They still are likely to be a playoff team, but the road ahead appears to have gotten tougher for the Jets, and unless trades add to the roster, Winnipeg is in for some adversity.

Now that GM Steve Staios is in his first full season as the architect of the Senators, his lineup decisions are painting a picture of a squad that should be more difficult to play against. 

Even after trading veteran D-man Jakob Chychrun to Washington and sending goalie Joonas Korpisalo to Boston, the Sens have added talent to the team, namely goaltender Linus Ullmark, D-man Nick Jensen and forwards David Perron and Michael Amadio. That should be enough to get Ottawa into proper contention for a post-season berth. 

The Senators are far from a perfect team, but they are improved from the team that underwhelmed last year. With some good fortune on the health front and internal improvement from their young core, better days are ahead for the organization.

It’s been a slow-and-steady off-season for the Canadiens thus far, with Montreal GM Kent Hughes focusing on extending youngster and rising star winger Juraj Slafkovsky to a cost-effective contract extension. 

Adding an elite prospect like 2024 first-round draft pick Ivan Demidov is another big piece of the puzzle for the Habs, even if Demidov won’t be in the NHL next season. 

Montreal is nowhere near being a legitimate playoff team, but they’re building the right way, and Canadiens fans should be pleased with what Hughes has delivered. It’s not easy to get back into the playoff picture once you’re out of it for years, but the Habs should continue to improve in 2024-25 and give the hockey world a glimpse of the very good times to come.

Ah, the Flames – not too long ago a team that had legitimate Cup aspirations but now one that is still figuring out what their identity will be over the long haul. 

As we said on the first day of free agency, adding veteran winger Anthony Mantha and defensemen Jake Bean and Kevin Bahl aren’t going to move the needle in the right direction for Calgary. GM Craig Conroy should actively participate in the trade market as he tries finding new homes for veterans, such as forward Nazem Kadri and MacKenzie Weegar, even if it's closer to the trade deadline after helping take the pressure off their younger players. 

The road back to the playoffs for Calgary is long and probably will be painful for Flames fans. But if they’re to acquire generational talents, it will have to happen via the draft. This year's draft was a good start, but that can't be it. 

A Cup is a pipe dream at this stage, but at least it appears management has come to terms with what needs to unfold for long-term success to happen.

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