This Season Could be the Toronto Maple Leafs’ Last Chance at a Cup in a While

This upcoming season looks to the be the Toronto Maple Leafs' best opportunity to make a deep postseason run given that fierce division and conference rivals may be headed for a regression after losing key players this offseason.
The Toronto Maple Leafs have the best chance to win a Stanley Cup since the 2021 all-Canadian division format.
The Toronto Maple Leafs have the best chance to win a Stanley Cup since the 2021 all-Canadian division format. / Maddie Meyer/GettyImages

This upcoming season could be the Toronto Maple Leafs’ last realistic chance at winning a Stanley Cup.

Before I get into why I believe this to be the case, let me make something clear: The Toronto Maple Leafs’ best chance at winning a Cup was in 2021 during the all-Canadian playoffs.

During those playoffs, the Leafs blew a 3-1 series lead against a Montreal Canadiens team that wouldn’t have been a playoff team during a normal season. As we all know, the Canadiens went all the way to the final where they fell to the Tampa Bay Lightning.

Since then, the Leafs have struggled to make any sort of headway in the Atlantic Division. They did get past Tampa once, but got promptly bounced in the second round. This past season, the Bruins did the honours once again.

But now, it seems that the major players in the Atlantic Division, and the Eastern Conference for that matter, have taken steps back. So, that opens up the door for the Leafs to make a run, potentially leading them to the Cup Finals.

Why This Season Could be the Toronto Maple Leafs Best Chance at a Cup

Let’s look at the state of affairs in the Atlantic Division. The Boston Bruins seemingly upgraded their club adding Elias Lindholm and Nikita Zadorov. Zadorov figures to be an expensive experiment, while Lindholm should deliver value.

Trading away Linus Ullmark to keep Jeremy Swayman seemed intelligent, but it could backfire. In short, the Bruins could be in for a regression if things do go according to plan.

Tampa Bay lost Steven Stamkos. To me, that’s telling because it seems like he’s jumping ship. While the Bolts resigned Victor Hedman and lured Jake Guentzel, it doesn’t seem like the Bolts will make much traction this season. In a bold prediction, Tampa could miss the playoffs.

That brings us to Florida. The Cats have lost several key depth pieces, including Oliver Ekman-Larsson and Anthohy Stolarz to the Leafs. While the Panthers’ core is still very much intact, it’s interesting that so many players would bail immediately following a Stanley Cup run. In my estimation, Florida is due for a regression.

With Boston, Tampa, and Florida potentially regressing, that situation creates a power vacuum the Leafs can take advantage of. Toronto could have an opportunity to win the Atlantic Division, possibly setting themselves up for a more favourable first-round matchup.

On the other side of the Eastern Conference, the Rangers look solid. But from what they showed in the Conference Final against Florida, they are vulnerable. The Hurricanes also lost a number of key players. While they too should be solid, they might not be as formidable as this past season.

Pittsburgh, New Jersey, and the Islanders should all be on the fringe of the playoff race. However, the team to watch in the Metro Division will be the Washington Capitals given the number of additions they’ve made.

All in all, the Leafs have a unique chance to capitalize on the last year of Mitch Marner’s contract, a healthy season from Chris Tanev, Auston Mattews and William Nyander in their primes, and John Tavares yet to experience any serious declinel.


Of course, the goaltending looks like it’s held together with duct tape. But as long as the tape doesn’t rip open, the Leafs could be facing the Dallas Stars, Colorado Avalanche or, why not, the Edmonton Oilers in the Stanley Cup Final.