After a slow start to the season following the departure of Mitch Marner, the Toronto Maple Leafs have started to kick their season into gear. With Auston Matthews finally beginning to hit his stride and Craig Berube once again whipping a team into shape as they enter the second half, just like he did in St. Louis, things are now looking positive for a team who was in major flux just a month prior.
And a lot of that success has come off the back of their elite goaltending. The tandem of Anthony Stolarz and Joseph Woll gave the Leafs two legitimate starting options last season, and this year, Woll has remained a great starting caliber goaltender that is capable of winning the Leafs games outright.
However, Stolarz has struggled with injury and underperformance this year, and has been out of the lineup since November. His absence re-opened the door for someone who struggled in 2024-25, the 6-foot-7 Swede Dennis Hildeby.
Flyers should trade for Dennis Hildeby from the Leafs to address goaltending
Hildeby made six NHL appearances last season after some solid AHL numbers, but wasn’t able to find his stride in short stints. But since Stolarz went down, he has been one of the better goalies in the league, and instrumental in helping turn the Leafs’ fortune around during a very pressure packed situation.
In 16 games, Hildeby has posted a 2.75 goals against average and a .916 save percentage while splitting time with Woll. And while the Leafs have only gone 4-5-4 in his starts, he still sports an impressive 7.4 goals saved above expected, which puts him in the company of starters like Darcy Kuemper and Filip Gustavsson, despite having played over 10 fewer games.
But with Stolarz’s return imminent, and both him and Woll locked up until 2028-29 to very reasonable cap hits, Hildeby is reaching a point where if he wants the consistent NHL time that he deserves, he may have to find it somewhere else.
At the same time, the Flyers sit at a crossroads with their own goaltending situation. Dan Vladar has been a revelation and taken over the starter’s role seamlessly up until this point, but his backup situation is up in the air. Sam Ersson, but all observable statistics, has been one of the worst goalies in the NHL this year, with an .858 SP% and a 3.33 GAA kind of speaking for themselves.
The Flyers and Leafs just recently completed a deal last season, when Scott Laughton went to Toronto in exchange for Nikita Grebenkin and a 2027 conditional first round pick. The relationship is open and cordial, and with the Leafs currently possessing a goalie surplus while the Flyers look for someone to link to the future at the position, it seems like there may be a fit between the two teams once again.
With the Flyers possessing a bunch of potential depth options in Lehigh Valley as well as in their current lineup, and the Leafs struggling with recurring injuries as they try to mount a playoff push, there could be a fit. Someone like Rasmus Ristolainen could help the Leafs out as they try and survive an injury to Chris Tanev, and with their defensive depth being spearheaded by names like Matt Benning and Philippe Myers, it may be prudent to look for an upgrade.
Hildeby’s value is going to be a bit hard to decipher given that he’s really only had this one stretch of consistently good NHL play, but there is a deal there that can be done without too many assets being tossed around that could benefit both sides into the future. If the Leafs are confident in their tandem, and Hildeby wants a real chance to prove that he can at least be an everyday NHL backup, a mutually beneficial move could help the Flyers add more depth at a position where they sorely need it.
