The Toronto Maple Leafs are going to have several tough questions to ask this summer, and one that hasn’t been talked about as much is the likely possibility of having to trade one of their many goaltenders this summer.

It may not have seemed as likely at the beginning of the year, but in a time where the Leafs have Dennis Hildeby waiting in the wings, it’s a real conversation that could be had. Hildeby proved in a small sample size this season that he’s ready to be a full time NHL goalie, and with the recent news of prospect Artur Akhtyamov being inked to a three-year contract extension, it seems likelier than ever that the scene is being set to deal one of Anthony Stolarz or Joseph Woll this summer, or perhaps even Hildeby. Goalie depth is important, and the Leafs are in a rare position where they can dip into that depth and seek some assets this summer.

The tough part of this conversation is deciding which two of these three to keep and which to dangle for assets. It will almost certainly come down to what they’re able to get for each goalie, and they each have a decent case to be the guy going forward. Let’s start with their NHLers. While Woll has been the more consistent goaltender over the years, Stolarz’s highs have been higher than any Leafs goalie in recent history, but in that same breath, he’s had some pretty low lows as well.

Both goaltenders have the unmoved mindset that’s needed to be a goaltender in Toronto, especially when expectations are as high as they currently are, so the question will likely come down to how the Leafs are approaching their entire goaltender situation, Hildeby and Akhtyamov included. Stolarz and Woll are currently making roughly the same amount of money, with the former getting $3.75 million annually and the latter coming in slightly below that, at $3.66 million. Stolarz’s deal won’t kick in until next season, leaving him on the books until 2030, while Woll’s contract expires following the 2027-28 season.

If the Leafs see genuine potential in Dennis Hildeby eventually being a starting goalie in the NHL, then it feels more likely that they trade Woll this summer and try to find a suitor for Stolarz in the coming years. Woll’s value will likely be higher given his age and manageable term, and if the plan is for Hildeby to be a starter down the line, you have to imagine that they’ll look to trade both of their goalies over the next couple of years.

At the same time, depending on their faith in Stolarz’s ability to rebound next season with less injuries and better performances, they could look to get out of his contract early. While Woll has never posted Vezina-level numbers in the NHL, he’s also never let his save percentage dip below .900 in the NHL. Even with the turmoil the Leafs have been in this season, Woll’s save percentage currently sits at .905 while Stolarz is at .894 after a stretch of decent games.

The other possibility here is that the Leafs decide to commit their faith to their current tandem and find a suitor for Hildeby. He doesn’t have an enormous sample size at the NHL level, but his numbers are better than either Leafs goaltender this season and he could be a worthwhile chance to take for a team looking to add a young starting goalie.

Either way, it doesn’t feel like the Leafs would have extended Akhtyamov by three years if the plan was to continue rolling Stolarz/Woll at the NHL level and having him tandem with Hildeby in the AHL. The extension was clearly an investment in Akhtyamov’s abilities to be a full-time starter in the AHL. Whether that means moving on from one of their NHL goalies and giving Hildeby a chance to be a tandem goalie in the NHL or using him as trade bait to give