Dennis Hildeby’s development will grow this year with this run that was created by Maple Leafs’ decision making to go harder on their other goalies, says David Alter.

It was just two years ago when a young Dennis Hildeby was called up by the Toronto Maple Leafs way ahead of schedule. With Joseph Woll sidelined with one of his many ailments and Ilya Samsonov struggling to find his game, the club leaned heavily on No. 3 goaltender Martin Jones while calling up the Swedish goaltending prospect. The problem was they called him up in his first year of hockey in North America, and Toronto’s fourth-round pick from the 2022 NHL Draft was never meant to be up with the pros so early.
Despite accompanying the team on a road trip through California, the Leafs never played him. With games scheduled on back-to-back nights, they chose to ride Jones instead, fearing they would ruin Hildeby’s development. Maybe it was the right call, since Hildeby posted a 3-3-0 record and a .878 save percentage in six appearances last season.
But with Toronto’s current goaltending duo in flux, Hildeby has shown, albeit in a limited sample size, that he’s up for the task. When Joseph Woll left the team for a month due to personal reasons, the Leafs relied on Cayden Primeau to back up Anthony Stolarz. Once they knew Woll was nearing a return, the Leafs saw enough from Primeau to put him back through the waiver wire, where the Carolina Hurricanes reclaimed him.
Hildeby has since been thrust into duty several times in relief when Stolarz has had to leave the game either due to performance or injury. Stolarz has been out for nearly a month with an upper-body injury, and the fact that he hasn’t been able to skate yet suggests his return won’t be happening any time soon. And with Woll out a week (perhaps longer given the history), the Leafs have had no choice but to throw their entire support behind the 6-foot-7 goaltender they call the ‘Beast’.
Through eight appearances, Hildeby has a 1-2-2 record but a .929 save percentage. He was the main reason the Leafs salvaged a point in a 2-1 shootout loss to the Montreal Canadiens on Dec. 6, making 33 saves on 34 shots. He is likely to start the club’s next two games or more, before Woll returns or the team makes another arrangement. But whatever happens, this will be a crucial year of development for the Swedish goaltender.
The Leafs went into this season without a veteran No. 3 and signed Hildeby to a three-year extension before the 2025-26 season started, knowing they’d need to possibly rely on him without a veteran goaltender around. The Leafs did add James Reimer on a professional tryout during training camp when Woll wasn’t around, but didn’t see enough to feel he was an upgrade over what they had.
When Hildeby had to come in for Woll after the latter suffered a lower-body injury in a victory against the Carolina Hurricanes on Dec. 4, he talked about the experience of coming into action in relief of a starter for the fourth time this season.
“Yeah, of course it helps. The more you do something, the better it feels,” he said. “It helps a little bit to learn.” Hildeby has certainly learned. And what has become quite evident is that the once-admired goaltending tandem of Stolarz and Woll doesn’t really function optimally when one of them isn’t available. Woll logged a season-high 42 games while Stolarz had 34 last season. Neither seems capable of ever hitting 50 games in a season. If Hildeby has taught the Leafs anything, it’s to not ride Woll or Stolarz hard when the other isn’t available. Hildeby is ready, and they should look to better manage the goaltending workload when two of those three are available.