Chayka's Strategic Moves.
Maple Leafs GM John Chayka Completes First Trade, Recalling Successful Arizona Deals.
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John Chayka has wasted no time making moves as the new GM of the Toronto Maple Leafs. On June 18, 2026, he sent goalie Joseph Woll and defenceman Simon Benoit to the Philadelphia Flyers. In return, Toronto received goalie Samuel Ersson, defenceman Emil Andrae, and a 2026 third-round draft pick, according to NHL.com.
The trade marks Chayka's first deal since taking the GM job on June 1, 2026 — his first NHL executive role since leaving Arizona in 2020. Toronto Sun noted the move was cold and calculated, with Chayka selling high on a popular player to get a younger, cheaper option in net.
Chayka Returns After Nearly Six Years Away
Chayka was hired by Arizona in 2016 at just 26 years old. That made him the youngest GM in major North American sports history. His methods were polarizing. He leaned heavily on data and analytics, often ignoring traditional scouting. He left the Coyotes in 2020 under controversy and spent nearly six years outside the NHL.
The Maple Leafs named him their 19th GM after a disappointing 2026 playoff exit, according to Sportsnet. At his June 15 press conference, Chayka promised "ruthless efficiency" and "asset optimization." He warned that big changes were coming before the draft.
What Toronto Gave Up and What It Got Back
Joseph Woll posted a 2.62 goals-against average and a .915 save percentage in 32 games last season. Samuel Ersson, who goes the other way, had a 2.78 GAA and a .908 save percentage — but in 51 games, a much heavier workload. Ersson is younger and cheaper. Toronto also gets puck-moving defenceman Emil Andrae, the type of mobile blue-liner Chayka covets.
Chayka said the move "secures our crease and our blue line for the next five years." Philadelphia GM Daniel Brière called Woll "a proven starter who has shown he can perform under the highest pressure," per Flyers News. The deal also gives Toronto a ninth pick in the first four rounds of the 2026 draft, adding lottery tickets to an already stocked draft haul.
Chayka's Best Arizona Deals Still Hold Up
Chayka's top moment in Arizona was drafting Clayton Keller 7th overall in 2016. Keller has since recorded at least 86 points in three separate seasons, according to HockeyDB. He became the face of the franchise and stands as the clearest proof that Chayka can identify elite talent.
Also in August 2016, Chayka pried power forward Lawson Crouse away from Florida. He took on $5.5 million in dead cap money — Dave Bolland's buried contract — but gave up no real players to do it. Crouse grew into a consistent 20-goal scorer, per The Athletic. The move showed Chayka's willingness to use cap space as a weapon, a strategy he is expected to repeat in Toronto with MLSE's deep pockets behind him.
Toronto Fans Split as the Analytics Era Begins Again
Reaction in Toronto has been sharp. Traditional media outlets criticized the deal as "trading heart for spreadsheets," according to Toronto Sun. Woll was a fan favourite — nicknamed "Brick Woll" — and Benoit was respected for his physical play. Losing both in one move stung many fans.
The analytics community pushed back. Sportsnet's Elliotte Friedman called it "cold, calculated, and high-risk," adding that Ersson's underlying numbers are "better" when adjusted for team defence. The trade also clears roughly $1.5 million in cap space, giving Chayka room to move when free agency opens July 1, per Edmonton Sun.
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