I’ll split this into 3 categories, because we have space to fill while the NHL is off to Italy for the Olympics.
The team isn’t where they wanted to be this season, which means that big changes should be made this summer. What I plan to do is run through everybody on the roster and the players that are/might be pushing for spots next season and discuss the ups and downs of keeping them, moving them and who may be available as a replacement.
The goaltenders will be a much quicker discussion than the rest of the roster.
The biggest issue with the Leafs’ 2026-27 goaltending situation revolves around Dennis Hildeby.
The question the Leafs have to ask themselves is if they want to keep Hildeby long term, or deal him now while his value is low. The reason this question exists is because he will no longer be waiver exempt at the beginning of next season. Unless the team wants to run a 3 goalie system, they’ll have to make a decision on one of the three goaltenders that have played in the NHL so far this season, as all are signed for at least another two years after this one.
Dennis Hildeby
The 6’7″, 231lb Swede has looked good, but not great in his time in the NHL. He has gone 5-6-4 this season with a 2.85GAA and 0.912SV%. At just 24 years old that’s not a knock on his performance, it’s simply the nature of the position. It’s true that goalies take longer to develop and it often happens that solid starters don’t break into the league until they’re in their mid 20s. Among the hottest young goalies in the league right now are Lucas Dostal (25), Jesper Wallstedt (23), Spencer Knight (24) and Yaroslav Askarov (23). Meanwhile, others are still developing and are fully expected to be starters at some point in the future. They include Joel Hofer (25), Sebastian Cossa (23) and as long as he isn’t a flash in the pan, Brandon Bussi (27).
While it’s unlikely that he has the same ceiling as some of those players, it’s not impossible. The simple fact of the matter is that he’s a huge goalie and if nothing else he takes up more net, which could easily translate into stopping more pucks. Among goalies that have played at least one NHL game this season he is tied for 1st in height and 4th in weight. Coincidentally he is tied with Mads Sogaard in both categories, as they are listed at the exact same 6’7″ 231lbs. I hope you enjoy that useless nugget of information.
One thing that is beginning to weigh the team down is their slow accumulation of useless contracts. Among the overpaid you’ll find Max Domi, Dakota Joshua, Morgan Rielly and, if they re-sign him, Matias Maccelli, probably. With Brad Treliving’s uncanny ability to waste cap space, Hildeby’s $841K caphit could be very useful.
In short, a cheap backup goalie that is young, has shown solid potential and is a literal giant is a good bet to keep around. If another team values him as a high ceiling prospect and will pay for that ceiling, then maybe you look at cashing in to fill a position of need. However, I feel that he has played well enough to deserve a shot as a backup in the NHL, but not well enough to convince another team to value him highly.
Joseph Woll
Joseph Woll has emerged as the teams starting goaltender this year. He’s the next youngest goalie at the NHL level, at just 27 years of age. The knock on Woll has always been his inability to stay healthy, but he has avoided injury for the most part this season. He still missed some time though, as he began the year by taking a personal leave of absence. It was never determined why he left the team (he deserves some privacy, like all of us) but they struggled without him out of the gate. It’s easy to think that the team could be much closer to a playoff spot if he hadn’t missed the first 17 games of the season, as he’s been that good since his return to the crease.
Woll is signed for two more seasons with a caphit of $3.667M per year, which is more than fair value for what he has delivered to the team over the past two years. Clocking in with a 13-7-4 record, a 2.87GAA and 0.910SV%, his stats are indicative of a team that plays poorly in front of him. He makes a lot of saves but he sees a ton of shots, which is why his save percentage and goals against average are both high.
Lastly, Woll’s play in the playoffs has been commendable, if nothing else. While his series against the Florida Panthers last year doesn’t look good on paper (3.56GAA, 0.886SV%), he played better than those numbers suggest. He was the backup during the first round, in which Anthony Stolarz was the starter, but stepped in after Stolarz was injured during Game 1 of the 2nd round. Jumping into the 2nd round of the playoffs can’t be easy, to say the least. While last season brought questions of “Would they have beaten Florida if Stolarz didn’t get hurt?” it was Woll that was on the other side of those questions not too long ago. During their 1st round series against the Boston Bruins in 2023-24, Woll got hurt in the last minutes of Game 6, which sidelined him for Game 7. They eventually lost that game with Ilya Samsonov in net, but we will always wonder if that would have been the case had Woll been healthy.
To summarize, Woll is still a young goalie in the NHL, he has shaken the injury bug for the most part over the past 2 seasons, is signed to a favourable contract and appears to have a great attitude, which is no small thing. If the team decided to move him you have to imagine that he would hold solid value.
Anthony Stolarz
The oldest of the trio, Stolarz (32) was a revelation for the team last season. His 2.14GAA and 0.925SV% stood among the best in the NHL. If he had been healthy all year he would have been in the Vezina Trophy conversation but, like Woll, he has always had trouble staying off the injured reserve list. Unlike Woll, it doesn’t appear that he has shaken the injury bug at all. He has already missed over two months of action this season, while there are still games to play.
The more worrisome thing with Stolarz and his injuries is how things unfolded at the beginning of this season. Towards the end of October he was seen wearing ice packs on both knees and was said to be feeling the effects of being overused. At the time the team was deploying Cayden Primeau as their backup goalie, but Primeau was playing very poorly, so they were riding Stolarz while they awaited Woll’s return. This begs the question, does Stolarz have the durability to be the starter throughout a long playoff run? Based on the events of October I think the answer is “no.”
Stolarz also called out his teammates for their poor play on the 19th of October and followed it up with poor play of his own. The positive side of this is that you can see the competitive fire inside of him, but if you’re going to publicly criticize your teammates for their poor play, you should be ready to put the team on your back directly afterward and spin it into a positive thing.
The 4 year, $3.75M AAV contract extension that was signed on September 28th has yet to kick in, which would mean that trading Stolarz now would raise some eyebrows. Yes, you can claim that the emergence of Dennis Hildeby and the further development of Joseph Woll has lead to the expendability of Stolarz, but it would still be true to say that they’d be walking away from him shortly after they decided to commit to him long term. Also, his previous contract held an 8 team NTC, but that upgraded to a 16 team NTC when he signed his extension, so he has some control over where he goes.
The positive side of his contract is that $3.75M isn’t a huge overpayment for a backup goalie, if that’s what teams view him as, especially with where the cap ceiling is heading. Stolarz can definitely carry the workload of a backup in the NHL and deliver a starting goalie quality performance when he is in net. Aside from his lack of durability, I would even argue that he has shown the ability to be the starting goalie outright. It’s actually possible that his most ideal situation would be as a 1B goalie to a young puck stopper with upside. I would assume that a team like the San Jose Sharks would jump at the opportunity to add Stolarz to their roster and run a Askarov/Stolarz tandem. The Philadelphia Flyers and Montreal Canadiens are also teams that, I assume, would have some level of interest.
Conclusion
In listing teams that would have interest in Stolarz it might sound like I would choose to move him and run a tandem of Joseph Woll and Dennis Hildeby next season… and you would be 100% correct in assuming that, because it’s true. However, that doesn’t mean that it is the only, or even the best option for a team that wants to win now. Stolarz is more proven than Hildeby and, as I said, would be a fantastic addition to a team that wants to support a developing starting goalie. One could argue that the Leafs are still developing Woll into a starting goalie and Stolarz is exactly what they need in order to help him get there.
It’s also a very real possibility that the Woll/Stolarz tandem could return to last season’s heroics when/if they’re given a fresh start, maybe even under a new head coach.
It’s also possible that a cap pressed team with goaltending issues would overpay for Dennis Hildeby. If you include him among the list of up and coming goalie talents in the NHL there’s no reason not to think that somebody would be willing to ante up for two more years of a young goalie on a fantastic contract.
You could also argue that the injury troubles that Woll and Stolarz have experienced in the past and present could mean that you’d possibly avoid the dreaded 3 goalie rotation if you kept all of them. There’s a fair chance that only 2 of the 3 goalies would be healthy at any given time and if all 3 were healthy, it wouldn’t last long. Therefore you get to kick a tough decision down the road a little, while also collecting as much information as possible before your final decision is made.
The possibilities are numerous, obviously. The only thing I see clearly at the moment is that this team isn’t a competitive group. I do think they’ll try to re-tool and come back better next season, but I don’t believe Brad Treliving has the vision or skill to build a true contending roster. With that in mind it could be a few more years before they’re ready to contend again so I’d keep the younger options, essentially rolling the dice on their upside, rather than hoping that Anthony Stolarz can continue to be an effective and healthy goalie into his mid 30s.