Tempered optimism reigns among Toronto Maple Leafs fans. The team’s retool this offseason has given incoming coach Jim Hiller some good pieces to work with. Plus, the addition of top-overall pick Gavin McKenna has boosted fans’ overall outlook on the club.
However, the optimism isn’t cut across the board. Quite the contrary, a sizeable chunk of the Maple Leafs fan base is actually quite bearish on the Leafs’ chances of winning a Stanley Cup.
A survey conducted by The Athletic revealed how fans feel about their teams’ chances of winning a Stanley Cup before 2036. 12% of Leafs fans reported feeling pessimistic about the club’s chances of hoisting a Cup ahead of that fate.
That’s the second highest rate, trailing only the Vancouver Canucks at 15%.
The Athletic asked fans: Which team are you most confident will NOT win a Stanley Cup before 2036? 🤔 👀 pic.twitter.com/E9C9ARpvOH
— NHL Forum (@NHLxForum) August 8, 2026
20236 may seem like a long time away. It’s roughly eight seasons from now. Given the trajectory the Maple Leafs are currently on, you would have to think that there could be a chance to win a Cup before then. For that to be true, the Leafs would have to win a championship within the next three to five seasons. The clock is already ticking with Auston Matthews’ contract up in two years. Meanwhile, the core, especially the blue line, continues to age.
That’s why the outlook isn’t all that rosy.
Maple Leafs staring at possibility of a rebuild
The last time the Maple Leafs were through a rebuild, it yielded a generation of players that have defined the franchise. However, extraneous circumstances, such as the COVID pandemic, cut right into the Leafs’ championship window.
It’s worth arguing that if COVID had never happened, and the cap had risen during the 2020, 2021, and 2022 seasons, the Leafs could have won multiple Cups.
Be that as it may, that once-promising core is now staring at the possibility of a rebuild. It’s a very real one, and that could be looming on the horizon.
If the club has another awful season in 2026-27, talk of tearing everything down and starting anew will continue to increase. John Chayka has pretty much a massive bet on the team this season. And if it doesn’t work out, the Maple Leafs will have to rethink their strategy heading into 2027-28.
Can Gavin McKenna save the Leafs?
It’s a romantic thought. Gavin McKenna comes in to save the Maple Leafs from obscurity, precluding the need for a rebuild. Toronto can avoid the worst parts of a rebuild, allowing the club just enough time to retool on the fly.
That’s a highly optimistic view. The reality would indicate that it’s not quite that simple. Yes, the Maple Leafs have one of the best young forwards to come out of the NHL Draft in a long time. If he turns into what Macklin Celebrini has, the Leafs will be in a fantastic spot.
Again, that’s a romantic view. Growing pains will likely ensue, but there might just be a good enough chance for the Maple Leafs to usher in a new era and extend championship aspirations for a little longer.
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