Canada’s Stanley Cup drought, explained, and how 3 teams can break it in 2025
Canada’s dry spell could end this year.
You’d be hard pressed to find anything innately funnier than Canada’s inability to win a Stanley Cup over the last three decades. The nation that gave us the sport of hockey, nurtured its culture, and provides over 40% of players in the league hasn’t had a team hoist the cup since 1993, when the Montreal Canadiens beat Wayne Gretzky and the L.A. Kings.
In that time we’ve seen teams from Florida win the cup four times, Carolina win once — even Las Vegas and Dallas have had their time in the sun. The Toronto Raptors have an NBA championship, the Blue Jays won a World Series, all while Canada’s collective hockey drought continued.
2025 could be the year that changes all that. Eight teams are left in the playoffs, three are from Canada. Winnipeg was the best statistical team in the NHL this season, the Maple Leafs showed major grit in beating the defending champions in Game 1, and Edmonton proved in the west that their top-line talent could overcome Vegas’ depth on Tuesday night.
Now comes the big test. Toronto takes the ice on Wednesday night to try and go up 2-0, and the Jets need to show they belong against Dallas following a series against St. Louis that was far too close for comfort. It’s time to dig into the three Canadian teams left and see whether they have what it takes to go all the way this year, and why they’ve struggled so much since the Canadiens win in 1993.
Edmonton Oilers
The Oilers will forever be inexorably linked to Wayne Gretzky’s legacy, and now they have the closest player to follow in his footsteps. Connor McDavid is such a phenom that Edmonton has largely been able to make the playoffs solely on the stick of McDavid and Leon Draisaitl, and it’s been that way for years.
The issue, as it perpetually has been, is that the Oilers lack defense and goaltending needs to make deep runs in the playoffs. They are very much built to be an incredible regular season team that lacks the depth needed to win a cup. For a while it seemed like there was a chance to change this, but the front office made the decision to keep McDavid and Draisaitl together — paying two enormous forward salaries, rather than letting Draisaitl walk and spending the money elsewhere.
This team has the potential to score in bunches and force teams into deep waters. It can be difficult to dig out, especially if the defense is on point. Unfortunately too often it’s not. It would be amazing to get McDavid a cup, but it’s iffy to bank on them against the field.
What’s gone wrong over the years?
Losing Gretzky was one thing, but the Oilers had a long, painful death after that which saw them slowly get worse and worse. The nadir really came after losing the 2006 Stanley Cup to Carolina, which led to some of the worst seasons in franchise history in quick succession.
This did allow the Oilers to land some phenomenal talent like Taylor Hall, Ryan Nugent-Hopkins, and the aforementioned McDavid — but the team over-invested in forward play at the expense of the rest of their team. They are a perennial playoff team now. They have the first line talent to make the Stanley Cup, but whether or not they can win is another story.
Toronto Maple Leafs
Every year there’s hope when it comes to the Leafs, and every year they find a way to blow it. The NHL’s equivalent of the Dallas Cowboys, Toronto is perpetually a team that looks brilliant on paper, yet finds ways to squander their talent when games matter the most.
This 2024-25 iteration of the Leafs is far from perfect. They’re a little too top-heavy in their lines and their penalty kill is middling, at best. Still, there’s no denying that something feels different about this Toronto team to past iterations.
It starts with the ludicrous talent up front. Only Edmonton can boast a similar level of star power. The first line Toronto has been using of Matthew Knies/Auston Matthews/Mitch Marner is a killer group, and being able to boast Max Pacioretty/John Tavares/Williams Nylander as a second line is just absurd.
When it comes to projecting their cup-winning potential it’s going to come down to two things:
- Can the Maple Leafs be strong enough on the forecheck to take pressure off their defense?
- Will Anthony Stolarz be able to hold up in net?
If Toronto can make it past Florida by proving No. 1, then they’ll have to content with either the Capitals or Canes to prove No. 2. If those both happen there’s a very real chance they could beat whoever comes out of the west.
What’s gone wrong over the years?
How much time do you have? Truth be told, it’s been a brutal five decades since the Leafs last won the Stanley Cup in 1967. Over that time they’ve made the playoffs 36 times and failed to even return to the Stanley Cup Finals. This is an organization that has made the playoffs in each of the last nine seasons, and never made it further than the second round.
A lack of star power has been the biggest problem. This is a franchise that has been so consistently good that they haven’t ever been quite bad enough to land superstar talent, at least until 2016 when the Leafs managed to draft Auston Matthews with the No. 1 pick. Matthews and Mitch Marner represent the best 1-2 punch this team has had in decades, and could ultimately be what puts them over the top.
Winnipeg Jets
The Jets were absolutely phenomenal during the 2024-25 regular season. Combining efficient offensive play with stellar defense allowed them to play an old-school game in the modern era. The kings of picking their shots, there was very little wasted momentum from the Jets all season long, and with the stellar Connor Hellebuyck in goal in allowed them to soar.
The problem has been these playoffs. Seemingly all at once the team has turned into a pumpkin. Predicting an easy Round 1 sweep against St. Louis seemed like a safe bet after their regular season dominance, but they were takent to seven games and were on the brink of elimination.
Defensively the team collapsed, Hellebuyck had massive issues finding the puck, and too often the Jets were pushed off their marks defensively, which opened up screens. Now they have to face Dallas, who are a favorite to win the cup after their trade deadline acquisition of Mikko Rantanen. It feels like their story might end in this series.
What’s gone wrong over the years?
Winnipeg was a victim of small market bias. The first iteration of the team had phenomenal success, but came just as NHL expansion was on the league’s mind. This led to their relocation to Arizona, abandoning the fanbase until 2011.
When the Atlanta Thrashers relocated to give Winnipeg a team it was a rough slog for a while, but the team built slowly into a contender. Now it seems they have all the parts needed to win a cup, so long as they can find their form again. The 2024-25 team is the result of years of work, and this might be the closest they’ll get for another decade.