As the Toronto Maple Leafs' best player since he arrived on the scene a decade ago, Auston Matthews is never far away from the spotlight.
The former Hart Trophy winner has kept a low profile since his 2025-26 season ended prematurely due to a knee injury; however, it's a safe bet that there have been many talks between the Toronto captain and the team's new general manager, John Chayka. Recent reports suggest the Maple Leafs still think very highly of Matthews.
Much of Chayka's offseason activity has been about surrounding Matthews with more talent and reshaping the roster to return the Leafs to the Stanley Cup playoffs. Appeasing Matthews and having a competitive team once again will help pave the way for the player and team to continue their relationship. Yet much remains to be determined before that happens, and a new deal between the parties is far from a certainty.
Breaking Down the Roadblocks to a New Leafs-Matthews Deal
The 2026-27 season will play a vital role in determining the future of the Maple Leafs and Matthews, who has two years remaining on his current contract. The good mojo from high-profile additions such as Gavin McKenna, Darren Raddysh, and Sergei Bobrovsky will be lost if the Leafs fall flat and have another dismal season.
Should both Matthews and the Leafs have success, the likelihood of extending the relationship increases, but it won't be simple. The recent Philadelphia Flyers sheet for Leo Carlsson of the Anaheim Ducks (with an $18 million AAV) and a rising NHL salary cap will have major implications moving forward.
In a recent article from Justin Arenburg of Sportsnet, Matthews was listed as one of five NHL stars who could demand max contracts. The current CBA allows a max contract to take up to 20% of a team's cap. In 2028-29, when a new Matthews deal would kick in, the NHL salary cap is projected to be $123 million. If Matthews asked for the maximum, it would be a $24.6 million cap hit in an escalating market.
As of now, that would be a difficult ask of the Leafs' captain. He is coming off two injury-plagued, down years, scoring only 60 goals over 127 games. What if Matthews has a third subpar season in a row? What if he again misses some games through injury? Should that happen, the Maple Leafs and Chayka would have to give serious pause to committing to Matthews. It would be a risk to sign him long-term at a big number if longevity becomes an issue.
Another X-factor in all of this is that Matthews is just one of the NHL's biggest stars scheduled to hit free agency in the summer of 2028. Connor McDavid and Zach Werenski will also be looking for new deals. Each has been lukewarm to extensions with their current teams.
Matthews, McDavid, and Werenski are all represented by the same agent, Judd Moldaver. The four will likely have ongoing conversations over the next two seasons, allowing for some fascinating possibilities. Player empowerment is at an all-time high across the league.
The Leafs' first-line center has always understood the significance of leading an Original Six franchise and has treated it with the proper reverence. Matthews knows what winning a championship in Toronto would do for his legacy. Yet, is he willing to stick it out if the Leafs haven't returned to contender status? He may look elsewhere for a title.
The 2026-27 season will play a key role in Matthews' future with the Leafs. A smooth, successful season under the new front-office regime of Chayka and Mats Sundin will increase the likelihood of both parties wanting to continue the relationship. The stakes will be high for the organization and the player.
Future negotiations between Matthews and the Maple Leafs, however, won't be a simple formality. In a landscape defined by soaring costs and an aging player with potential physical vulnerability, finding a middle ground is no slam-dunk, leaving the franchise's immediate direction in the balance.
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