It’s a bit of a surprise, but Toronto Maple Leafs general manager John Chayka executed his first major trade as general manager. Joseph Woll and Simon Benoit are heading to the Philadelphia Flyers, in exchange for defenceman Emil Andrae, goaltender Samuel Ersson and a third-round pick in the 2026 NHL Draft.

Although some may question why the Maple Leafs would trade their nominal starting goaltender, Toronto is dealing from a position of relative strength. Artur Akhtyamov and Dennis Hildeby have both proved they’re ready for a larger role at the NHL level, while Chayka secures some more draft capital, in his first summer with the team. The real key for the Maple Leafs will be Andrae.

Andrae registered two goals and 13 points in 61 games with the Flyers last season, before adding an assist in four playoff games. He’s a 24-year-old left-handed defenceman who was selected in the second round of the 2020 NHL Draft. Andrae didn’t always live up to internal expectations with the Flyers, but Philadelphia controlled 55 percent of the expected goals at 5-on-5 when he was on the ice in 2024-25, along with a 51 percent share in 2025-26 via Natural Stat Trick. He’s an immediate upgrade over Benoit, and considering his age, upside and skating ability, it’s a clever step in trying to aim for a younger, mobile defence corps. Andrae is currently an RFA, and the deal may be truly evaluated on the terms the Maple Leafs eventually sign him to. For the time being, he’s a younger, cost-effective option.

Ersson-for-Woll is another variable to consider here: Woll is the superior goaltender, to be clear, by a wide margin. Ersson is one of the NHL’s worst full-time goaltenders, posting a gaudy .870 save percentage in 2025-26. This is clearly why the Flyers made the trade, as they can now pair Woll with Dan Vladar, who is coming off a tremendous campaign, where he earned down-ballot Vezina consideration. Philadelphia believes it has found its goaltending tandem of the future, for a relatively light acquisition cost.

Ersson will have to fight for his spot on the Maple Leafs, with Anthony Stolarz, Akhtyamov and Hildeby ahead on the depth chart. Perhaps this is where the Maple Leafs justify the move, where Ersson’s NHL experience could be a differentiator in what could be a crowded battle.

It’s a bit of a shock to see Woll leave after spending his entire career with the Maple Leafs. He will get a new start with one of the NHL’s rising upstars in Philadelphia, while the Maple Leafs aim to rebuild their defence corps one block at a time. It’ll be compelling to reevaluate this deal a year or two from now, especially after seeing where Andrae and Ersson fit into the Leafs’ long-term plans.