Hildeby’s proven himself to be worth more ice-time in the starter’s crease for the Maple Leafs, and he’s loaded with untapped potential. While both youngsters should be in the long-term plans for Chayka and Mats Sundin, the same can’t be said about Joseph Woll or Anthony Stolarz. While their contracts are very reasonable at $3.6 million AAV for two more seasons for Woll, and a new four-year extension kicking in for Stolarz July 1, which has him signed through the 2030 season at $3.7 million AAV. Woll doesn’t have trade protection until July 2027, meanwhile, Stolarz’s no-trade clause kicks in on July 1, and he owns a 16-team no-trade list.
At this point, it’s a wait-and-see approach to see how everything shakes out, but what we do know is that the Maple Leafs are very likely going to trade from a position of strength, which will result in one of their four goaltenders traded at some point this summer. Here’s five teams to put on your radar as potential trade partners:
Edmonton Oilers
What a disastrous season for the Oilers’ crease in 2025-26, after GM Stan Bowman tried to do his best to address their issues. That resulted in a tandem of Tristan Jarry and Connor Ingram heading into the playoffs, which in the end, wasn’t close to enough talent to help get Connor McDavid and company back into the Stanley Cup Final.
Philadelphia Flyers
The Flyers are going to be active in the trade market this summer, as you have to feel it’s slightly bittersweet for them to watch former netminder Carter Hart leading the Vegas Golden Knights to the Stanley Cup Final. GM Daniel Briere will be involved in trade discussions on a number of different aspects of his hockey club, including finding a tandem partner to pair with Dan Vladar next season, and beyond.
Vladar only has one season left on his contract, so you know Briere will be interested in all four Maple Leafs’ goalies, who are all signed for at least two seasons, and Stolarz for the next four. With Stolarz’ familiarity with the Flyers’ organization, Philadelphia is very likely a team he’d approve a trade to this summer.
New York Islanders
The Islanders are in the market for a reliable backup for Ilya Sorokin this summer, and they’re very likely one of the teams who have recently been calling Chayka about Akhtyamov. The Islanders proved last season they aren’t shy on the trade market, and with their newfound lease on life with Matthew Schaefer arriving, now GM Mathieu Darche will be pushing to fill out his roster in the best way possible, as soon as possible.
Sorokin would be a perfect mentor for Akhtyamov to learn from and this is certainly a duo that could do big things on Long Island. The Isles have a slew of young forwards who will be searching for regular NHL playing time as soon as next season, including Cole Eiserman, Cal Ritchie, Victor Eklund, as well as one of the best defensive prospects in hockey in Kashawn Aitcheson.
Chayka would be wise to sweeten his trade offer to try and land one of the four top prospects mentioned, than move one of his goalies for someone like Anthony Duclair, who the Isles are going to dangle in offseason trade talks.
Pittsburgh Penguins
It feels like now with Treliving gone, the Penguins have become a potential trade partner moving forward. Kyle Dubas still has many ties to the Maple Leafs’ roster and knows a ton about Woll, Hildeby, and Akhtyamov.
The Pens are likely letting Stuart Skinner walk this summer, and while they have a couple of AHL netminders who will push for NHL minutes next season, look for Dubas to add talent in net to push Arturs Silovs for starter’s minutes. With Dubas’ preference to get younger, it wouldn’t shock me at all to see Hildeby moved to Pittsburgh this summer.
As far as potential trade options in return, the Penguins have 22-year-old d-man Owen Pickering, who would push for a regular job on the Maple Leafs’ blueline next season. It’s no secret Chayka is looking for mobile, two-way defencemen who can advance the puck, and join the rush, and Pickering is loaded with untapped potential to become a solid top four option moving forward.
Winnipeg Jets
There’s been plenty of trade rumors coming out of Winnipeg this summer, after what was a very disappointing season for the Jets. Connor Hellebuyck’s name has been floating around as a potential superstar who could be moved this summer, but what’s far more likely is seeing the Jets add a cost-effective, and talented number two goalie behind Hellebuyck, to help manage his workload in 2026-27.
22-year-old Brad Lambert is a former first-round pick who had a down year and saw his name floated around trade rumors. Prospects Colby Barlow and Brayden Yager are close to pushing for regular NHL minutes and could certainly interest Chayka. Defenceman Elias Salomonsson is a 21-year-old right-handed defenceman, who appeared in 32 games for the Jets last season. The former second-round pick has middle-pair potential, and someone who can contribute to both sides of special teams, while also playing a hardnosed, physical game. There’s a lot to like with Salomonsson’s game, so if these two teams materialize a trade this summer, don’t be surprised to see the Swedish defenceman included.
While these five teams are going to be in the market for goaltending depth, the Maple Leafs could have some competition with their offers from teams like the Montreal Canadiens, Vancouver Canucks, and St. Louis Blues, who are all going to be active in goaltender trade talks.
At the end of the day, Chayka should be seriously considering moving one of his goalies this summer, as it’s a position of strength, and a well-constructed trade could allow the Maple Leafs to fill holes throughout their lineup.
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