John Chayka wasted little time making over the Toronto Maple Leafs’ goaltending picture, and the ripple effects have already pushed one of the organization’s most intriguing young netminders out the door.
Before Chayka was hired, Toronto’s crease looked crowded and deep. Anthony Stolarz, Joseph Woll, Dennis Hildeby, and Artur Akhtyamov all saw NHL action for the Maple Leafs in 2025-26. Stolarz, Woll, and Hildeby each got into more than 20 games, while Akhtyamov was a major part of the Toronto Marlies’ AHL Calder Cup run.
That surplus gave Chayka room to move. With limited trade chips elsewhere, he reworked the goalie depth chart.
His first deal as Leafs GM sent Woll and Simon Benoit to the Philadelphia Flyers for puck-moving defenseman Emil Andrae. Then, during free agency, he flipped Hildeby and draft picks to the Tampa Bay Lightning for Nick Paul.
Hildeby’s path in Toronto was already narrowing. If the Maple Leafs weren’t going to carry three goalies to open the 2026-27 season, he would have had to clear waivers to get back to the Marlies. That made a move likely, and Toronto chose to deal him rather than risk losing him for nothing.
For Leafs fans, the whole thing brings back an old and painful memory: Tuukka Rask.
Toronto drafted Rask in the first round, 21st overall, in the 2005 NHL Draft. Justin Pogge came in the third round, 90th overall, in 2004. With both prospects in the system and neither ready to take over, the Leafs sent Rask to the Boston Bruins in June 2006 for starting goalie Andrew Raycroft.
Pogge’s strong showing at the 2006 World Junior Tournament - a 1.00 goals-against average and a .952 save percentage - helped shape that decision. He also had a couple of strong seasons with the Calgary Hitmen of the WHL.
The long-term result was brutal for Toronto. Pogge played only 7 NHL games, all with the Leafs, then spent the rest of his career bouncing through minor leagues and Europe.
Rask, meanwhile, stayed in Boston for his entire 15-year career and piled up franchise records for games played (564) and wins (308), building a borderline Hall of Fame case. Raycroft had one decent season in Toronto before eventually being put on waivers and bought out.
Now the Leafs are hoping this story ends differently.
Chayka chose to keep Akhtyamov over Hildeby, betting on the goalie who was the organization’s pick during the Marlies’ championship run. Hildeby had the better numbers for Toronto last season, finishing with a 2.86 goals-against average and a .914 save percentage in 20 appearances. But Akhtyamov’s playoff work stood out: he went 15-7 with a 2.22 goals-against average, a .923 save percentage, and two shutouts.
The two goalies are nearly the same age, both soon turning 25, and both are on track for more regular NHL work before long. Akhtyamov is expected to spend most of next season with the Marlies, though he could be called on by the Leafs if Anthony Stolarz or Sergei Bobrovsky gets hurt or needs rest and maintenance. Hildeby, meanwhile, is lined up to back up Andrei Vasilevskiy in Tampa Bay, where the star goalie is a free agent in 2028.
So Toronto will be watching both sides of the split: one young goalie still in the system, the other now wearing a division rival’s colors. The Leafs are clearly hoping this one doesn’t turn into another Rask-sized regret.
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