The Maple Leafs are about to lose a goalie for nothing unless they trade Joseph Woll first
Photo credit: Marc DesRosiers-IMAGN Images
If the Toronto Maple Leafs aren't careful this summer, they could lose a goalie for absolutely nothing and it would be a huge oversight on John Chayka's part.
Toronto has a surplus of goaltenders but not enough room for Joseph Woll, Anthony Stolarz and Dennis Hildeby. That means they are likely going to make a deal involving one this summer, and they probably should - or they are going to lose them on waivers for nothing.
John Chayka walked into the Maple Leafs GM job with one of the best goaltending tandems in the league with Joseph Woll and Anthony Stolarz. But not only that, he inherited a pretty great pipeline that includes Dennis Hildeby and Artur Akhtyamov.
Woll and Stolarz need waivers while Hildeby is ready to make the jump so Toronto needs to tread carefully
It's a wealth of talent that few teams have the luxury of enjoying, but there comes one massive caveat. There's only two goaltending spots to lock down, and with potentially all four men vying for NHL work, one of them will most likely need to be dealt away.
Chayka has to make sure that he doesn't let this situation get too far past him however, considering that he's going to lose a goalie for nothing if he stays quiet. Toronto can't pass Woll or Stolarz to the Marlies if beaten out because they have to go through waivers and no NHL team is passing up on them.
While Hildeby does have a two-way contract for 2026-27, if the goal is having him as the goaltender of the future then he's only got one more year of flexibility; but they can't afford to keep him stuck in the AHL if he's ready to make the jump.
This past season, Hildeby posted a 5-7-4 record but his numbers were much better than his record suggests. He had a 2.86 GAA and .912 SV% while also recording a shutout and looked much more comfortable in the big leagues.
Philadelphia needs a goaltender and Joseph Woll has the most value to trade away
If he takes that into training camp, along with a solid AHL season and make a real statement (plus unknowns about Stolarz and Woll's health) then Chayka has no choice but to deal away one of his netminders.
That would presumably be Woll, given that he is younger, on a shorter deal, and doesn't come with the same injury concerns as Stolarz does. Anthony Di Marco reported that the Philadelphia Flyers may pivot to Woll if they are moving on from Samuel Ersson; so there's potential there:
If the Flyers elect to go in a different direction, Joseph Woll of the Leafs is a name sources had indicated to DFO as a name the Flyers like.
It makes sense as to why the Flyers would target Woll given that he fits their timeline and is still young enough to keep them relevant for the next few years or so. In terms of a return from the Flyers, we could see someone like Owen Tippett come the other way.
With a logjam at wing and Toronto needing a big improvement up front, Tippett makes sense as a crash-and-bang power forward who can do just about everything and comes at a very reasonable contract.
Porter Martone, Trevor Zegras and Tyson Foerster are all top-tier players meanwhile Matvei Michkov, Alex Bump, Nikita Grebenkin, and Philip Tommasino are all vying for wing spots as well. Tippett may be expendable and Toronto is ready to scoop him up.
With Toronto needing that forward boost and Philadelphia needing to shore up their goaltending, it makes a lot of sense to swap Woll for Tippett; especially if Dennis Hildeby is ready to go.
But if John Chayka waits too long then he's going to have to live with the fact that one of them is going to leave whether he likes it or not.
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