John Chayka’s First Big Maple Leafs Decision Might Be in Net
About a year ago, the Toronto Maple Leafs were looking at their goaltending tandem of Anthony Stolarz and Joseph Woll and feeling pretty good about it. On paper, it looked stable enough. They had two goalies who could share the load and give the team decent nights most of the time. At times, it actually looked like one of the better setups in the league.
Fast forward to 2025-26, and things feel a lot less settled. Between injuries, inconsistency, and the rise of Dennis Hildeby as a legitimate NHL option, the team suddenly finds itself in a spot where it might actually have to make a decision instead of just riding the tandem out.
Together, Woll and Stolarz represent a huge Maple Leafs health issue?
The situation with Joseph Woll and Anthony Stolarz is actually pretty interesting, because when they’re both healthy, they genuinely have the potential to be one of the better goaltending duos in the NHL. The problem is, they’re not always healthy — and that’s the big issue. You just can’t fully count on them night to night.
Together, they don’t take up a huge chunk of the salary cap, since both are under $4 million, making it a very efficient tandem on paper. But that’s where the real question comes in: can you actually trust the availability, or are you always going to be dealing with one of them being banged up or unavailable at any given time?
Woll is the home-grown guy fans have been waiting on, and there’s still a belief he can become a solid NHL starter, but he’s missed time with both personal reasons and injuries, and it’s hard to build consistency in net when he’s not regularly available. Stolarz, meanwhile, is in the same boat in a different way. He also missed a big chunk of the season with nerve issues. So it’s not really about talent with either of them; it’s more about whether the Leafs can rely on them over a full season, because right now that’s the lingering question hanging over both.
Dennis Hildeby got a chance and looked good.
And while both goalies were out at different points, Dennis Hildeby stepped in and actually held his own. The 24-year-old former fourth-round pick played 20 games and posted a .914 save percentage. That’s not just “emergency fill-in” numbers — that’s real NHL backup-to-1B type production.
Now the big wrinkle? He needs waivers. And that changes everything.
The Maple Leafs could technically run a three-goalie system, but that’s rarely ideal, especially over a full season. So now you’re in that uncomfortable middle ground: if Hildeby is good enough that you can’t lose him for nothing, and both veterans come with availability questions, something eventually has to give.
New GM John Chayka is going to have to earn his keep.
That’s where the front office earns its keep. Because if Toronto can turn one of Stolarz or Woll into value — and keep Hildeby in the mix — they might actually come out of this with a deeper system, more flexibility, and maybe even a bit of draft capital on top. It’s not an easy call. But it’s starting to look like a necessary one.
It will be interesting to see how Chayka treats this issue.