It’s fair to say that Monday’s news conference announcing the Toronto Maple Leafs’ new general manager is going to be remembered and talked about for a long, long time in this city.
We’ll see if it’s for the wrong reasons.
Word that John Chayka was in the running to be the Leafs’ next top hockey executive first hit my inbox at the start of April. A source with longstanding connections to the team sent over an article from a site I hadn’t heard of that stated Chayka had talked to the team about a position as far back as February, well before previous GM Brad Treliving had been fired.
I responded that it felt unlikely, even if he was on the long list of candidates. (MLSE president Keith Pelley said Monday he spoke with 27 altogether during the search process.)
Within a week, however, it became clear Chayka was a finalist for the role as they began to cut down to four names. Another two weeks later, he appeared to be Pelley’s top choice.
Along the way, as his candidacy became more of a sure thing, I received unsolicited texts and calls from several executives around the NHL who wanted to talk about just what was going on in Toronto with the team’s GM search.
The reality is many around the league are baffled by the Leafs’ decision, to the point that it’s become the No. 1 soap opera in hockey circles. That’s why it didn’t shock me when the news conference was overshadowed by the now-viral question about Chayka’s credentials and character.
It was telling, too, that when Sportsnet’s Elliotte Friedman sat down with Chayka shortly after the media gathering, one of his first questions for the new GM wasn’t about his vision or mandate. It was about this perception problem that appears to be widespread.
Chayka may have been out of the league since 2020, and only in the GM’s chair in Arizona for four years before that, but he certainly made an impression. And it wasn’t a great one.
“People are looking for reasons to come after you,” Friedman said at one point in his conversation with Chayka, as they addressed a new report about tampering allegations that landed before he had even officially taken the Leafs job.
That’s not a typical statement you’d see posed to an incoming hockey ops hire. In fact, none of this is normal business when it comes to these kinds of announcements. Many controversial candidates seem to get treated with kid gloves at their introductory media availability, with their past failures ignored and the redemption arc part of the story of the day.
It makes one wonder why this Chayka situation is unique: Why is he, in particular, so polarizing in a league where underperforming retread executives are recycled every offseason?
To me, this whole situation is a perfect storm, one where multiple factors — including some that have little to do with Chayka’s past — are at play. There’s the Leafs’ historic plummet down the standings this season, combined with Pelley coming in as a new face of ownership, and the stories about dysfunction behind the scenes.
Then you layer in Chayka’s background as the NHL’s youngest GM ever, during a tenure in Arizona that went sideways on the ice and off — in more ways than one — plus his suspension, followed by a long tenure out of the league. The way Chayka reportedly treated Shane Doan at the end of his career is another frequent criticism you hear, too.
Many who were around the Coyotes at the time believed Chayka wouldn’t get another opportunity with an NHL team, given all that went on.
“Everyone’s pretty shocked,” said Craig Morgan, an Arizona-based sportswriter who covered Chayka’s time there for The Athletic. “I thought he might be blackballed.”
Chayka didn’t seem inclined to fully reflect on those past failures on Monday. Asked what he had learned after his mistakes in Arizona, Chayka repeatedly tied them back to what was happening with the Coyotes at the time in terms of the ownership changes and lack of a suitable arena. “Stability is critical,” he said, “and we have that here.”
“I’ve made decisions I’m proud of, and I’ve made mistakes I’ve learned from,” Chayka said in a prepared statement when he was introduced by Pelley. “I’m human. I own all of it, and I’m better because of it.”
The fact the new Leafs GM comes from an analytics background is likely part of the pile-on from outside, too, as that isn’t unusual from the old-school crowd — although the hiring of New Jersey Devils GM Sunny Mehta, also analytics-minded, last month wasn’t received this way at all.
You combine all of that in the league’s biggest, hottest market, and it has the makings of a potential sideshow.
So, in addition to Chayka’s relative inexperience and poor track record as a GM, you have this other, unusual challenge layered on top, where few people around the league are anxious to give him a second chance. This is the pool of execs he is going to need to work with to pull off trades and potentially hire help from, assuming he’s going to turn over some of Toronto’s front office in the coming months. And he will need to win over players and their agents, too, if the Leafs are going to add in free agency or sign players to contract extensions.
“We’re not worried about the outside,” Chayka told Friedman when asked about his reputation serving as an impediment to success. “We’re going to focus on our team and what we can control. In terms of me personally, I’ve always tried to act as professionally as I can, be a good communicator, work with people to understand what they’re looking to do in terms of transactions, and I think if I can continue to do that my history has been I’ve been able to make good transactions for the team. That’s my focus.”
Make no mistake, this was a strange hire by MLSE for a number of reasons, including the fact that Mats Sundin is along for the ride in his first-ever management role with an NHL team. (If anyone acquitted themselves well on Monday, it was the former captain.) But the pressure on Chayka and the Leafs is going to be dialed up to a level well beyond anything he faced in Arizona, with his peers in executive roles and the media all looking for the first signs of failure.
The deck was always going to be stacked against anyone who took on this role given the state of the roster and ownership’s insistence on turning things around quickly, something I believe will be exceptionally difficult. But Monday’s news conference highlighted a few more hurdles and the intense skepticism the Leafs are going to face going forward.
A lot of the attention may be on Chayka and his past right now, but if this goes sideways in Toronto, it’s ultimately not going to be on him. It’ll be on an organization that has been adrift for a while now, one that appears caught off guard every time there’s criticism and struggles to explain its actions, even when it comes to something as vital as why it made this hire.
None of it feels like a recipe for success. Only more chaos.
