Which Goalie Do Maple Leafs Trade This Offseason?
Joseph Woll, Anthony Stolarz, and Dennis Hildeby are all under contract.
All three will be on one-way deals next season, meaning all three require waivers to be sent to the AHL.
Three NHL-caliber goalies cannot coexist on one roster without one of them being wasted, and John Chayka's first summer as Maple Leafs GM includes finding a trade partner willing to take one off his hands.
The question is which one.
The Case Against Trading Hildeby
The consensus across multiple outlets is that Hildeby should not be the one who goes.
The 24-year-old Swede is signed for two more seasons at $841,667 per year before his contract converts to a one-way deal in 2026-27, making him the most affordable and the most developmentally promising of the three.
Elliotte Friedman: Re Maple Leafs: People are looking for goalies and they have a surplus; they have to basically decide are they gonna have Dennis Hildeby be their backup next year or risk losing him on waivers - 32 Thoughts (5/27)
— NHL Rumour Report (@NHLRumourReport) May 31, 2026
He appeared in 20 games for the Leafs last season and was exceptional, and his work in the Marlies' AHL playoff run further cemented his status as a legitimate NHL-ready option.
The most popular feeling is that Hildeby is someone Chayka and Mats Sundin should protect in their long-term plans, noting that his untapped potential and bargain contract make him a building block rather than a trade chip.
The Hockey News echoed the same argument, pointing out that Hildeby and prospect Artur Akhtyamov, who posted a .928 save percentage in the Marlies' final four run, could eventually form the long-term tandem Toronto builds around.
The Case for Trading Woll
Woll is the name generating the most consistent trade interest around the league.
He is 26 years old, signed for two more seasons at $3.6 million per year, does not have trade protection until July 2027, and has been linked to the Edmonton Oilers, New Jersey Devils, and Philadelphia Flyers in separate reports.
Toronto Maple Leafs are expected to test the trade market on one of their goalies, Joseph Woll or Anthony Stolarz.
— Hockey 24|7 (@iamhockey1) June 2, 2026
The challenge about moving Woll is the same one that applies to any Toronto goalie trade: neither Woll nor Stolarz has ever been a true number one starter, and their combined injury histories mean the depth behind them matters more than it would for a healthier tandem.
The Case for Trading Stolarz
Stolarz is the more complicated conversation.
He signed a four-year, $15 million extension that kicks in July 1, locking him in through the 2030 season at $3.7 million per year.
His save percentage dropped to .893 this season, well below his career average of .914, and he appeared in only 26 games due to injury.
The Toronto Maple Leafs are expected to test trade waters on one of Joseph Woll or Anthony Stolarz. Per, David Pagnotta.
— The Mug NHL (@TheMugNHL) June 2, 2026
H/T @PuckEmpire
The no-trade clause he receives on July 1 includes a 16-team list, which limits Chayka's flexibility considerably and means any deal involving Stolarz needs to be completed before that date or requires Stolarz's cooperation on a destination.
The window to move him without those complications is shrinking fast.
Woll seems to be the trade most likely to happen.
He is tradeable immediately without NTC complications, his $3.6 million cap hit is digestible for any team in need, and the market for young goalies with his track record is consistent enough that Chayka can expect a good amount of competition between multiple interested parties.
Moving Woll allows the Leafs to give Hildeby a real path to NHL playing time alongside Stolarz in the short term while Akhtyamov continues developing in the AHL.
Photo Credit: James Guillory-Imagn Images
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