John Chayka did not take long to restructure the Toronto Maple Leafs' goaltending situation. Before the general manager was hired, that position was considered one of the deepest in the organization.
Anthony Stolarz, Joseph Woll, Dennis Hildeby, and Artur Akhtyamov all saw action with the Maple Leafs in 2025-26. Stolarz, Woll, and Hildeby all played in twenty-plus games with the Leafs, while Akhtyamov was the key figure in the Toronto Marlies' AHL Calder Cup title.
With too many capable netminders and few trade assets elsewhere, Chayka reshuffled the Leafs goaltending depth chart. In his first trade as Leafs GM, he moved Woll and Simon Benoit to the Philadelphia Flyers for puck-moving defenseman Emil Andrae. During free agency, Chayka then traded Hildeby and draft picks to the Tampa Bay Lightning for Nick Paul.
Unless the Maple Leafs carried three goalies to start the 2026-27 season, Hildeby would have needed to clear waivers to play with the Marlies. Neither was likely, so the Leafs moved him to Tampa Bay. Now, the organization hopes history doesn't repeat itself since the last time the team had two top goalie prospects to choose from.
Dennis Hildeby vs. Artur Akhtyamov: Echoes of Rask vs. Pogge
The Maple Leafs and their fans can be excused for not wanting to be reminded of Tuukka Rask. Rask was drafted by Toronto in the first round, 21st overall, in the 2005 NHL Draft. Goaltender Justin Pogge was drafted by the Leafs in the third round, 90th overall, in 2004.
With two top goaltending prospects in their system, but neither ready to carry the load, the Maple Leafs traded Rask to the Boston Bruins for starting goaltender Andrew Raycroft in June of 2006. Part of the reason for trading away Rask was Pogge's dominant performance in the 2006 World Junior Tournament, with a 1.00 goals-against average and a .952 save percentage. He also had a couple of strong seasons with the Calgary Hitmen of the WHL.
Pogge only played 7 NHL games, all with the Leafs. He spent his career bouncing around various minor leagues and then Europe. Rask played his entire 15-year career in Boston, setting franchise goaltending records for games played (564) and wins (308) with a borderline Hall of Fame resume. The Maple Leafs had the unfortunate reminder of one of the worst trades in franchise history every time they played their division rival for a decade and a half. Raycroft had one decent season with Toronto before the Leafs eventually bought out his contract after putting him on waivers.
Fast forward twenty years, and Toronto hopes it hasn't made a similar mistake. Chayka had to do something about the Maple Leafs' glut of netminders, so he traded Woll and kept Akhtyamov over Hildeby, from the team's two best young goaltending prospects. Paul fills a need to help the Leafs' bottom-six forwards, a team weakness for some time now.
Hildeby had the best stats of any Leafs' goaltender last year, posting a 2.86 goals-against average and .914 save percentage over 20 appearances. Yet, Akhtyamov was the organization's goalie of choice in the Marlies' run to the Calder Cup title. He put up stellar numbers in the playoffs, going 15-7 with a 2.22 goals-against average, a .923 save percentage, and two shutouts.
Both Akhtyamov and Hildeby are of similar age (soon turning 25) and will each soon be seeing more regular NHL duty. Akhtyamov is set to spend most of next season with the Marlies. Yet, he is likely to see action with the Leafs if Anthony Stolarz or Sergei Bobrovsky get injured or need rest and maintenance. Hildeby is slated to back up the Lightning's star goaltender, Andrei Vasilevskiy, a free agent in 2028.
Now, the Maple Leafs and their fans will watch to see how two of their developed, highly touted goaltending prospects fare in their NHL careers, one on their own roster, the other with a division rival. This time, the organization and its fans hope for a happier outcome.
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