The Maple Leafs new GM might be the worst hiring in sports history

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.

His marquee move shortly after being hired was to destroy the only bright spot Coyotes fans had for the better part of 20 years. Franchise legend Shane Doan had requested one final season to take a retirement lap with the Coyotes, offering to move back to the third or fourth line and take short shifts to make it happen — but Chayka released him instead. The ultimate slap in the face, and one that has marginalized Doan from the organization to this day.

Despite being billed as an analytics wunderkind, there was no evidence during Chayka’s tenure with the Coyotes that he had any appreciable skill in the area. Despite making wholesale roster changes and hiring his own head coach, the Coyotes saw no dramatic improvement in either their standard .500-level hockey, or in their style of play. In addition, the three drafts he oversaw were largely disastrous, netting no quality top-line players who are still with the organization, while also managing to force the team to forfeit a 1st and 2nd round pick after Chayka was caught conducting a private scouting combine, against NHL rules.

This is how veteran hockey reporter John Gambadoro characterized Chayka’s time with the Coyotes.

“This is incredible. Chayka was a total fraud here. Cost the Coyotes first and second round picks for cheating. Quit on the team right before the bubble. Stabbed Don Maloney in the back to get the gig here.

The way he treated Shane Doan was despicable. He wanted him gone, and would not even consider letting him play one last year on the third line. He was just jealous of him. Chayka is a fake. Only his connection to Tie Domi is getting him this job.“

Toronto’s decision to hire Chayka is frankly unbelievable. His track record reflects a history of failure, and he has been out of hockey since he quit the Coyotes in 2020. This is a man who has not been around the game in six years, now handed one of the most high-profile front office jobs in the entire sport. Not only that, but there are serious questions about how the Leafs settled on Chayka. There are at least credible reports that the reason for the hire was due to Chayka’s friendship with the Domi family, being a personal friend of Leafs’ forward Max Domi, and by extension his father, Toronto legend Tie Domi. It’s also been reported that the Domis introduced Chayka to Mats Sundin, who is now a senior advisor to the Leafs.

It’s impossible to see this ending well. The Maple Leafs braintrust are unable to give any justification for why Chayka was hired, people around the NHL are laughing at the move, and now it’s more of a question of how much damage Chayka will do in Toronto, rather than the amount of improvement we” see in Toronto.