The Toronto Maple Leafs and new general manager John Chayka have already had an active start to the NHL offseason. With the draft less than a week away and free agency just around the corner, league-wide action is sure to pick up.
The Maple Leafs got a head start on reshaping their roster by making a trade with the Philadelphia Flyers, moving Joseph Woll and SImon Benoit for Emil Andrae, Samuel Ersson, and a third-round pick. Next, Chayka completed a sign-and-trade with the Tampa Bay Lightning for Darren Raddysh.
It is likely only the start as Chayka and the Leafs try to bounce back from a last-place finish in the Atlantic that resulted in missing the playoffs for the first time in ten years. With a new front office, speculation has mounted about how far roster changes might go and other players in Toronto who could be involved.
TSN Insider Pierre LeBrun Addresses the Future of Several Key Leafs' Players
Due to Toronto's regression in 2025-26, speculation has surrounded Leafs' captain Auston Matthews and his future with the team. Since his season-ending press availability, Matthews has not been heard from. During an appearance on TSN's OverDrive, hockey insider Pierre LeBrun was specifically asked about his confidence level in Matthews being on Toronto's opening night roster to start 2026-27.
While reluctant to guarantee a return, LeBrun explained that it was his understanding that Matthews intends to be in Toronto next year, giving it a ninety-five percent chance of happening. The insider said that a return wasn't officially stated by Matthews and his agent, Judd Muldaver, but it has "more or less been communicated."
LeBrun stated that communications between Muldaver and Chayka have been frequent and that "it's absolutely pointing where Matthews will at least give Toronto another year." As Matthews has watched the Leafs' offseason unfold, with a GM and coaching hire, player transactions, and likely more to come, it has persuaded him to stick around.
When asked about the Maple Leafs next moves, LeBrun has heard Toronto has been busy exploring improvements across all areas, including goaltending, forwards, and defense. He specifically noted that there is still a lot of talk in league circles about Matthew Knies.
LeBrun added that he still believes it is unlikely that Knies gets traded, as mentioned before by Chayka, but that his name is still prominent in talks and teams are presenting offers.
Discussion then switched to the longest-serving Leaf, Morgan Rielly, and where things stand with his no-move clause. LeBrun said Rielly is open to a move and that teams like the Anaheim Ducks and San Jose Sharks would be high on the defenseman's list of destinations. The insider added that Rielly sent a Western Conference heavy list to the Leafs.
LeBrun's insights confirm that Maple Leafs' management is likely to continue to be busy. As the NHL offseason reaches its peak time for player movement, it's clear Chayka and the Leafs could just be scratching the surface of their roster turnover.
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