Did the Maple Leafs Give Up on Dennis Hildeby Too Soon?

Some former Maple Leafs players are easy to forget once they leave town. Dennis Hildeby probably shouldn't be one of them. Hildeby gets his first preseason start with the Tampa Bay Lightning on Tuesday against Nashville. It's only preseason, of course, but there is something worth watching here. The former Maple Leafs goaltender is beginning a new chapter, and Toronto might eventually have to watch from a distance to see how it turns out.
Hildeby Gets a Fresh Start in Tampa.
Hildeby had a pretty interesting season in Toronto in 2025-26. He appeared in 20 games and finished with a 5-7-4 record, a 2.85 goals-against average and a .912 save percentage. Those numbers are respectable, and they tell only part of the story. There were stretches when Hildeby looked like a young goalie who was starting to believe he belonged. He came in and gave the Maple Leafs stability, and there was a stretch when Toronto seemed to have its best chance to build momentum with him in the crease. Now he's gone.
The Maple Leafs moved on from Hildeby as part of their changes in the net, eventually bringing in Sergei Bobrovsky. That's the business side of hockey. Teams make decisions based on what they think gives them the best chance to win. But that doesn't mean those decisions always tell us what a young player will become.
Related: The Matthews Question the Maple Leafs Haven't Answered Yet
Hildeby Is One of the Former Maple Leafs Worth Watching.
That's probably why Tuesday's start in Tampa catches the eye. Hildeby will begin the season as Vasilevskiy’s backup, which might be a pretty good place for a young goaltender to learn. He'll get to watch one of the league's established goalies, work with a new coaching staff and wait for his opportunities. If those opportunities come and he plays well, things can change pretty quickly for a goaltender.
And that's what makes following Hildeby fun from a Maple Leafs perspective. Joseph Woll is doing the same thing in Philadelphia, beginning a new chapter of his own. Toronto's goaltending picture looks very different now, but the players who were once part of it haven't suddenly stopped being interesting.
Maple Leafs Fans Have to Wonder Where Woll and Hildeby Will Be a Year from Now.
Sometimes the easiest thing in hockey is to judge a young player by where he fits today. The more interesting question is where he might be a year from now. Hildeby gets another chance Tuesday. This time, the Maple Leafs won’t get to see up close what he can become.
But if you are a fan, it might be worth watching anyway.
