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Auston Matthews Could Soon Face a Connor McDavid-Style Dilemma

Originally posted on NHL Trade Talk | Last updated Sep 2, 2025 11:52 AM ET

While the loss of Mitch Marner will sting, the Toronto Maple Leafs are in a good spot this season when it comes to the status of their other key stars. Unlike several teams who have big-name free agents making decisions before July 1, Auston Matthews, William Nylander and others are all under contract for a few more seasons.

That said, not everything is a secure as it might seem.

According to James Mirtle of The Athletic, the Maple Leafs might not be far away from having to worry about Matthews’ future. With three years remaining on his deal, Matthews is inching closer to the same crossroads Connor McDavid faces today in Edmonton this summer— questioning whether his team can truly deliver a Stanley Cup and if Toronto is the right place to lock in.

The Leafs have built in some financial flexibility to make bold in-season moves, much like Florida did last year when it added Brad Marchand and Seth Jones en route to a Cup Final berth. But those short-term fixes won’t erase the pressure to prove to Matthews — and the rest of Toronto’s pending 2026 free agents — that the Leafs are serious contenders.

Mirtle writes:

“I think it’s vitally important they have a strong 2025-26 to convince not only him but also those 2026 UFAs that Toronto is a place they can potentially win.”

What If Matthews Starts to Question the Leafs?

The parallels to McDavid’s situation are striking. In Edmonton, the lack of a contract extension for the league’s top player has created constant speculation and distractions. The longer it drags out that he doesn’t sign, the more there will be questions about his future, even if he’s never given a solid reason to assume he won’t stay. Toronto could be facing a similar narrative by the 2026-27 season if Matthews enters his final season without clarity on what comes next.

Mirtle suggests the Leafs should be aggressive as they continue building their roster because another season without playoff success could convince Matthews this isn’t where he’s best suited to win a Stanley Cup. Perhaps like McDavid, winning is the top priority for the Toronto star. And, while the feeling is McDavid is pushing the Oilers to prove their consistent contenders, the Leafs can get ahead of things by proving it now.

Another early playoff exit might push Toronto into the same anxious situation Edmonton fans are now facing. They’re confident McDavid will sign, but no one really knows for certain. The coverage over every word McDavid says (and doesn’t say) is intense. Matthews situation will be as loud, if not louder.

Matthews’ confidence in the organization will ultimately hinge on results, not potential.

If Toronto can’t prove it’s a true contender soon, the league’s spotlight will turn from McDavid (when he signs) to Matthews, even though he’s still two years away from having to make a decision.

This article first appeared on NHL Trade Talk and was syndicated with permission.

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