Auston Matthews and the Maple Leafs are heading into a stretch that could decide everything about their future together.
Matthews has spent a decade as Toronto’s top player and remains the face of the franchise, but his next contract is anything but a lock. He has stayed mostly out of sight since his 2025-26 season ended early because of a knee injury, even as reports point to ongoing conversations with new general manager John Chayka. The Leafs, for their part, still appear to hold Matthews in very high regard.
Toronto’s offseason has been built around him. Chayka has worked to add more talent and reshape the roster in hopes of getting the team back to the Stanley Cup playoffs.
If the Leafs can get Matthews happy and back into a competitive environment, that goes a long way toward keeping the relationship intact. But there are still plenty of moving pieces, and nothing about a new deal should be considered automatic.
The 2026-27 season looms as the biggest one yet in sorting out what comes next. Matthews has two years left on his current contract, and the Leafs need that season to go well if they want any real momentum toward an extension. If the club stumbles again, the goodwill created by additions like Gavin McKenna, Darren Raddysh, and Sergei Bobrovsky could evaporate fast.
There’s also the money. Justin Arenburg of Sportsnet recently included Matthews among five NHL stars who could push for max contracts.
Under the current CBA, a max deal can reach 20% of a team’s cap. With the salary cap projected at $123 million in 2028-29, the year a new Matthews contract would begin, that would mean a $24.6 million cap hit if he asked for the maximum.
That kind of number would be tough for Toronto to swallow right now, especially with Matthews coming off two injury-plagued seasons. He has scored 60 goals over 127 games in that span, and another season like that - or another stretch interrupted by injury - would force the Leafs to think hard before making a long-term commitment at a massive price.
The market around him only makes things more complicated. Matthews is one of several major names set to hit free agency in the summer of 2028, alongside Connor McDavid and Zach Werenski.
All three have been lukewarm on extensions with their current teams, and all three are represented by Judd Moldaver. That shared representation could lead to plenty of interesting conversations over the next two seasons, especially with player empowerment at such a high level across the league.
Matthews has long shown he understands what it means to lead an Original Six franchise, and he has treated that responsibility with respect. He knows exactly what a championship in Toronto would mean for his legacy.
But if the Leafs still aren’t back in contender territory, would he wait around? He could decide the best path to a title is somewhere else.
So the 2026-27 season isn’t just another year for Matthews and the Leafs. It may be the year that decides whether this partnership keeps going or starts to drift apart.
Under Chayka and Mats Sundin, a strong season would improve the odds of a new deal. A weak one would make the future far less certain.
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