The Maple Leafs new GM might be the worst hiring in sports history
TORONTO, ONTARIO - MAY 4: John Chayka speaks at a press conference he was announced as General Manager and Mats Sundin is introduced as Senior Executive Advisor of Hockey Operations of the Toronto Maple Leafs at Real Sports Bar & Grill on May 4, 2026 in Toronto, Ontario, Canada. (Photo by Michael Chisholm/Getty Images) | Getty Images There’s a certain level of expectation when it comes to the Toronto Maple Leafs making a hiring. Like the Yankees, Lakers, or Cowboys — seeing the Leafs struggle brings joy to hockey fans with a sense of schadenfreude, but even in that shameful joy exists a kernel of empathy that makes you feel bad when the team does something monumentally stupid.
The Leafs did something monumentally stupid on Monday. So stupid, in fact, that there’s a very good chance they now own the title of making the worst general manager hire in the history of professional sports. The team announced that John Chayka would ushering in a new era of hockey in Toronto, and tell me if you have ever heard a response like this from a reporter Steve Simmons or the Toronto Star at the team’s press conference.
“You talk about the due diligence that you did on John prior to hiring him, and now hiring him. In the past three-to-four days I have been in contact with about 20 people who work in the National Hockey League, many of whom are prominent names that we would all know — and of the 20 people that I spoke to, one was supportive of John’s hiring, and the other 19 thought it was a sham, to be perfectly honest. Words were used like ‘con artist, liar, salesman.
’ How did you come to a different conclusion than I was able to come to in a very short period of time. ” The back-and-forth between Simmons and Leafs president Keith Pelley didn’t stop there, as the team representative offered a curt “I must have spoken to different people,” before being pressed again. It was sublimely awkward considering John Chayka was sitting right there hearing how people think he’s a fraud — but the criticism isn’t wrong.
Chayka was hired in 2016 as the general manager of the Arizona Coyotes in a move that was surprising at the time. Chayka was a hot-shot analytics geek, who was stunningly taking over an NHL franchise at the age of 26-years-old. The youngest GM by a mile, it was a move couched more in disruption than sound logic, and it wouldn’t be long before the people learned that Chayka was an utter fraud.
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