The Toronto Maple Leafs officially finalized their front office over the weekend, introducing John Chayka as general manager and Mats Sundin as executive advisor on Monday.
Chayka and Sundin won’t have much time to settle in, with plenty already on their plate, though nothing is more important than determining whether they have any chance of keeping captain Auston Matthews in Toronto long term.
According to TSN insider Chris Johnston, there remains significant uncertainty surrounding Matthews’ future. The superstar center is not yet willing to commit to being a Maple Leaf for even the 2026–27 season until he sees what the new management group does to improve the roster this offseason.
“This, while inheriting a cupboard woefully short on assets, in a year where NHL free agency leaves a lot to be desired, and at a moment where the future of franchise player Auston Matthews remains very much in question. Matthews has two years remaining on his contract, but still isn’t sure if he’ll be back in Toronto in the fall, according to league sources,”
The only sales pitch Matthews needs at this stage is real action, according to league sources. Before committing to another season in Toronto, he wants to see a roster that has been meaningfully upgraded through trades and free agency. This isn’t about selling him on a fancy 12-point plan or a bunch of vague promises. Seeing is believing. Effectively, the Chayka-Sundin front office will be auditioning for the team’s most impactful player with their work around draft week in late June and the opening of free agency on July 1. As such, they shouldn’t expect any commitments from Matthews about his future until some point after that happens and he can evaluate where the team stands heading into 2026-27,”
The 28-year-old Matthews, as mentioned, has two years left on the four-year, $53 million extension he signed with the Maple Leafs in 2023, eligible for a new extension come July 1, 2027. He’s coming off a career-worst 53-point (27 goals, 26 assists) 2025-26 campaign.
There is certainly a lot of pressure on Chayka and Sundin, and how the draft lottery unfolds on Tuesday could be the first domino to fall in shaping Matthews’ thinking.
Reports have consistently suggested that Matthews wants to stay and win in Toronto, but after such a messy year, it’s fair to wonder whether he might be better off taking his talents elsewhere.
Next: Raptors Could Already Dangle Brandon Ingram on the Trade Market?
