Why Dennis Hildeby Has Become the Maple Leafs’ Best Trade Chip

The Toronto Maple Leafs have spent years trying to solve their goaltending puzzle, and now, almost out of nowhere, they have the opposite problem: too much of a good thing. Three NHL-calibre goaltenders are a luxury in this league, but it’s also the kind of luxury that forces uncomfortable questions.

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With every solid start Dennis Hildeby gives them, the story shifts a little less toward ‘glut’ and a little more toward ‘asset management.’

Hildeby’s Situation Is Unique

Hildeby’s situation is unique. He’s young, calm, structured, and on the cusp of losing his waiver exemption. That detail matters more than most fans realize. Once that exemption disappears, he becomes tough to hide. If the Maple Leafs tried to send him down, he’d be claimed instantly. Every team in the league wants a young, cost-controlled goaltender who doesn’t rattle. Hildeby fits that profile better than most.

But this only becomes a real conversation if Joseph Woll and Anthony Stolarz are healthy and playing at the deadline. Right now, injuries have forced Toronto’s hand. Woll’s lower-body issue and Stolarz’s upper-body injury have made Hildeby a necessity, not a luxury. And he’s handled it exactly the way a future starter should—steady, efficient, unbothered by the moment. That alone has raised his stock.

If Woll and Stolarz Are Healthy in March, Then What?

If Woll and Stolarz are back and in rhythm by February or March, the team suddenly has something they haven’t had in years: a goaltending tandem they trust. Stolarz is signed to a four-year term, which gives Toronto stability. Woll’s contract is team-friendly, and his modified no-trade clause doesn’t kick in until later. Both, when healthy, have the numbers to back up the belief that they can hold down the crease.

And that’s where the question comes in: if the Maple Leafs are healthy in net, is Hildeby actually their best trade piece?

It’s not far-fetched. Toronto doesn’t have many assets that they’re eager to move. They’re not breaking up the core. Their prospect pool is thin at the top. Their cap situation leaves no room for a splash unless something meaningful goes out the door. A young goaltender who looks NHL-ready, who still hasn’t hit his ceiling, and who can be marketed as a long-term solution? That’s rare currency.

Timing Would Also Be a Deal for the Maple Leafs

There’s also a timing element here. Hildeby’s value might never be higher than it is right now: strong NHL play, no waiver risk yet, and a market full of teams that desperately need stability in net. Once that exemption expires, the dynamics change. His value slips because GMs know Toronto’s hand is weaker.

But moving him now would still be a gamble. Woll and Stolarz have both shown they can play at a high level—when they’re on the ice. Neither has an Ironman history. If the Maple Leafs trade Hildeby and lose a goalie to injury in March or April, they’re suddenly exposed again. It’s the kind of decision contenders dread: talent versus timing, depth versus opportunity.

Is It Too Soon to Think “Move Hildeby?”

So, is it too early to consider moving Hildeby? Not at all. It’s too early to decide anything, but it’s precisely the right time to think about it. If Woll and Stolarz return healthy and stay that way, Hildeby becomes more than a third goaltender. He becomes the piece that could buy Toronto what it can’t afford any other way—help on defence, depth for the playoffs, or a missing ingredient they’ve been looking for.

For now, Hildeby keeps playing, and the Maple Leafs keep watching. But the conversation has already shifted. The question isn’t whether he can play in the NHL. It’s how long Toronto can afford to keep him.

Related: 5 NHL Trade Chips: The Best Bang for the Buck?