As the 2026 NHL Trade Deadline creeps closer, the Toronto Maple Leafs find themselves navigating a tricky - but potentially pivotal - situation in goal. With injuries sidelining both Anthony Stolarz and Joseph Woll, the Leafs turned to Dennis Hildeby, and the 23-year-old didn’t just fill in - he made a statement.
Hildeby’s emergence has been one of the more intriguing storylines for Toronto this season. In 19 games, he's posted a .912 save percentage and a 2.90 goals-against average - solid numbers for a goalie thrust into NHL action without much notice.
He’s shown poise beyond his experience, stepping up from his role as the Marlies’ starter in the AHL and proving he belongs on the big stage. That kind of performance doesn’t go unnoticed - not by fans, not by coaches, and certainly not by other teams.
Enter the Philadelphia Flyers.
The Flyers are reportedly in the market for goaltending help, and Hildeby has surfaced as a name of interest. Given their current situation in net, it’s not hard to see why.
Philadelphia lacks a clear-cut starter and could be looking for a long-term solution or at least a reliable piece to shore up the position. Hildeby, with his size, calm presence, and upside, fits the bill.
But here’s where things get interesting for Toronto. They don’t have to make a move.
They’ve got three NHL-caliber goaltenders - a luxury most teams would love to have down the stretch. However, with other holes to fill and the future always in mind, the idea of moving one netminder for assets has to be on the table.
If the right offer comes along, it could help the Leafs both now and later.
Still, if you’re the Leafs, trading Hildeby isn’t a decision you make lightly. He’s young, he’s homegrown, and he’s shown he can handle the pressure of NHL minutes.
That’s a tough combination to find, and it’s even tougher to let go of - especially for a team that’s been burned before by letting promising talent walk. The memory of Fraser Minten’s departure is still fresh, and Toronto won’t want to repeat that kind of misstep.
So what’s the alternative? Offering up Anthony Stolarz might make more sense.
Stolarz is a known quantity. He’s signed to a new deal that kicks in next season, and he’s proven he can handle the workload when called upon.
He’s also got history with the Flyers - they drafted him back in 2012 and gave him his first NHL shot in 2016. That familiarity could make for a smoother transition and a better fit in Philadelphia’s crease.
From Toronto’s perspective, moving Stolarz would allow them to keep Hildeby in the fold, continuing his development in a tandem role with Woll or whoever else is healthy down the stretch. It’s a move that balances short-term flexibility with long-term potential - something this franchise has to be conscious of as it tries to stay competitive in the Eastern Conference.
At the end of the day, the Leafs have options. Whether they stand pat, move a veteran like Stolarz, or entertain offers for Hildeby depends on the offers that come in and how confident they are in their internal depth. But one thing’s clear: Dennis Hildeby has played his way into the conversation - and possibly into Toronto’s future.