The Toronto Maple Leafs are once again at a crossroads, looking to prove they are dead serious about contending for a Stanley Cup in 2027. Despite the star power upfront, the club still has glaring holes throughout the lineup.
One of the most glaring holes is in the crease.
This year’s tandem of Joseph Woll and Anthony Stolarz was hardly what the team needed. Yes, there were stretches in which both goalies played well. But it wasn’t good enough to sustain a true playoff push.
That said, the Maple Leafs may have an opportunity to land an all-world goalie. That would be Winnipeg Jets netminder Connor Hellebuyck.
During his exit interview at the end of the regular season, Hellebuyck was evidently upset about the way the Jets’ season went.
Could it be that Hellebuyck might twist Winnipeg’s arm into trading him? If that’s the case, he’ll want to go to a team that’s on the verge of winning a Cup or to a team that would put him on the NHL’s biggest stage.
That team could be the Maple Leafs.
It wouldn’t be the most insane idea in the world for the Maple Leafs to engineer a trade for Hellebuyck. While Toronto is hardly as Stanley Cup contender at this point, the Leafs have been slightly closer to a Cup than the Jets.
Plus, there’s always the allure of playing in a market like Toronto. While the same could be said about the New York Rangers or Detroit Red Wings, the Maple Leafs would offer Hellebuyck to be the star of the NHL’s most high-profile club.
Hellebuyck Has Solid Relationship with Maple Leafs Captain
One major selling point for the Maple Leafs is the relationship between Hellebuyck and Auston Matthews. Both were members of the 2026 US Olympic team that captured gold in Milano-Cortina.
As such, that nexus could be one that Toronto might exploit in luring Hellebuyck to the Maple Leafs. That’s no guarantee that Hellebuyck would be willing to move his full no-trade clause to join Toronto.
But then again, it would be much worse if he went to a team without any real familiar faces. Bringing Hellebuyck to Toronto would also convince Matthews that the Maple Leafs are serious about contending. With an all-world goalie in the mix, the Leafs could become instant favorites in the Eastern Conference.
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The Logic Behind this Massive Deal
Hellebuyck is under contract for five more seasons at $8.5 million AAV. So, the only plausible way for the Maple Leafs to land Hellebuyck would be the 32-year-old going to the Jets and demanding a trade. Moreover, that demand would be something along the lines of, “I want out. Send me to Toronto.”
By painting the Jets into a corner, Hellebuyck could pretty much pave the way for the Maple Leafs to make the trade happen. The Jets would have no other recourse but to take whatever the Leafs have to offer. For instance, a top-five pick in the 2026 NHL Draft wouldn’t be a bad idea in this situation.
As for the likelihood of such a trade happening, that’s an entirely different story. Such a trade would be quite the longshot. But stranger things have happened in the NHL. After all, who would have thought that Artemi Panarin would end up in Los Angeles? Yet, it happened.
Maple Leafs Trading for Jets Goalie May Not Be Totally Insane Idea