3 Maple Leafs set to lose their waiver eligibility next season

"Of the three, Hildeby is the only one under contract and the one who looks to have a future on the Maple Leafs roster. He is finishing up his fourth year in the NHL, and that is enough to set him loose on the waiver wire. Make no mistake, he would be claimed instantly."

"Hildeby's NHL numbers were spectacular last season, even if there is still a lot of work that needs to be put in. His AHL numbers highlight that Hildeby isn't a finished product, but his upside is hard to ignore, and if the Leafs aren't ready to move on from the Woll/Stolarz tandem, there will be a team ready to give Dennis a regular spot in their NHL net."

"Hildeby's waiver status forces John Chayka to immediately make a tough decision in net. Anthony Stolarz is an asset on a reasonable contract, but has a very rough 2026-27 hanging over him, and hasn't been able to push past 34 regular season starts in the NHL. There's a market for him, but moving Stolarz would be more about clearing cap space than accumulating assets."

"Joseph Woll appears to be a Steady Eddie option for the Maple Leafs and would draw the eyes of teams around the league looking for a young-ish option in net who could be a stabilizing presence on a lot of teams. The Leafs could cash out on him, but would be handing the net over to Stolarz, who may give the Leafs 30 games, Hildeby, who is still a work in progress, and trusting that Artur Akhtyamov is ready to be the third option."

Dennis Hildeby is the key waiver-eligible player for the Toronto Maple Leafs next season. He is under contract, finishing his fourth NHL year, which makes him subject to waivers and likely to be claimed immediately. His NHL performance last season was strong, while his AHL results show he is still developing. If the Leafs are not ready to move on from the Woll/Stolarz tandem, another team could offer him a regular NHL role. His waiver status creates pressure on John Chayka to decide in goal. Stolarz has a difficult 2026-27 outlook and limited start totals, so trading him may be more about cap relief than asset gain. Woll could attract interest as a stabilizing younger option, while keeping Hildeby would require confidence in his readiness or development path.

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