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The Toronto Maple Leafs are heading towards a crossroads this summer. After being perennial contenders for years, the club took a massive step backwards in 2025-26. In fact, Toronto went from Atlantic Division champions to finishing last in the division in just one year.

Not only did the Maple Leafs struggle mightily this past season, but things could get worse before they get better. Superstar forward Auston Matthews could very well end up wanting out of Toronto. Although his current $13.2 million AAV contract does not expire until 2028, Matthews may ask for a trade this summer. The club’s captain recently admitted that he cannot “predict the future” during exit interviews in April.

NHL insider Chris Johnston is now reporting that the situation has not eased, and league sources are telling him that Matthews “still isn’t sure” if he will return for the 2026-27 campaign. According to Johnston, the superstar needs reassurances from the club that the roster will be drastically improved. Matthews will be 29 by the time the next season starts and wants to win a Stanley Cup title.

“The only sales pitch Matthews needs at this stage is real action, according to league sources,” claims Johnston. “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.”

Toronto Maple Leafs Will Have Difficulties Appeasing Auston Matthews

GettyAuston Matthews recorded his lowest point total of his Maple Leafs career in 2025-26.

The problem for the Toronto Maple Leafs and Matthews is that it seems difficult for the club to improve at the moment. Toronto does not have a lot of quality draft capital to help facilitate trades. Everyone in the organization will be crossing their fingers that they receive a top-five selection in the upcoming draft. If the Maple Leafs get a pick outside of this range, the selection would go to the Boston Bruins due to a previous trade.

Free agency typically helps a struggling team get better as well. Toronto does have ample funds to work with in this area, too. Nevertheless, the 2026 free agent class is widely considered extremely weak overall. The Maple Leafs can only hope that forward Alex Tuch and defenseman Darren Raddysh become available in July. Outside of the dynamic duo, there is not a ton of star power to be had in the market.

Toronto Criticized for Recent Management Hirings

At the time of Matthews’ precarious remarks about his future with the Toronto Maple Leafs, he specifically mentioned how new management would improve the roster. Since then, the team has hired John Chayka as their new GM and Mats Sundin as a senior advisor. The moves have been widely criticized by NHL reporters.

It remains to be seen how Matthews feels about the hirings, but it will all come down to how the duo navigates the offseason. Matthews wants to compete for a Stanley Cup in the near future, and Toronto execs have to improve the roster for this to happen. Johnston, however, has claimed during an interview with TSN’s First Up that this seems to be “mission impossible.” If so, Matthews may have played his last game with the Maple Leafs.