John Chayka’s hiring by the Toronto Maple Leafs in early May to serve as the team’s 19th general manager in franchise history was met with questions and skepticism from the media and fans alike.
The noise around the Maple Leafs and 37-year-old Chayka, who hadn’t worked in the NHL since an unceremonious end to his tenure as the Arizona Coyotes’ GM in 2021, has quieted over the past few months.
A fortunate draft lottery win leading to the selection of Gavin McKenna, a handful of player acquisitions including defenceman Darren Raddysh, goalie Sergei Bobrovsky and forward Nick Paul, as well as the naming of new head coach Jim Hiller, have formed a sense of optimism for the team entering the 2026-27 campaign after the disaster that was last season.
The main decision maker behind the Chayka hiring were president and CEO of Maple Leaf Sports & Entertainment Keith Pelley. However, Neil Glasberg, president and CEO of PBI Sports, also played a major role in finding Brad Treliving’s replacement as he was hired to run the search committee.
Glasberg described the task of hiring the next general manager of the Maple Leafs as an “incredible exercise.”
“We exhausted the universe of candidates, as you can imagine. Very high-profile job, lots of alumni interest. I was amazed actually at the number of Leafs alumni that reached out that said they wanted to be part of the process. It was really genuine and really cool that guys bleed Leafs’ blood, really wanted to add value,” explained Glasberg during an appearance on TSN 1050’s First Up on Monday morning. “The unfortunate thing is we have lots of people and one job.”
Glasberg said even though they spoke to “north of 25 people” not every single person received a formal interview.
Glasberg and Pelley worked hand-in-hand during the process to get the number down to a manageable number where a decision could be made.
“There were a lot of people reaching out to Keith. Keith was forwarding them on to me. As you can imagine, these searches take a ton of time. The value in the search is the educational component, what you learn from people. So, these are people interviewing for the job that say this is what I can bring, this is what I would do,” said Glasberg. “Between the two of us, we actually talked to everybody. But as I said, some people had more formal interviews, other people had more casual interviews and then at the end of the day you have to pare down your list to a manageable number because you just don’t have the time and energy.”
Glasberg added it wasn’t his job to make the final decision on who would serve as the next general manager, but rather to highlight the best candidates and get them prepared for the formal interviews.
“I want everybody to go in with the same agenda, so to speak. I mean what they want to do individually is their call but I wanted everybody to be ready to be able to answer the questions to the best of their ability,” he said. “It was a collaborative effort and there was a committee, it wasn’t just Keith and I. There was a committee of three people that was that was running this for MLSE and I was the search guy. I was the ‘here’s who I think we should seriously consider and here’s why.’”
Glasberg has helped many other teams lead their searches for various front office roles and says it usually comes to the “best fit” for that specific franchise.
“At the end of the day it really comes down to looking at the universe of candidates and understanding who’s got the best skill set, who’s the best fit, that was the word I use all the time, because there are a lot of people who have the competencies, but the fit may not be there,” said Glasberg.
According to Glasberg, one of the qualities that gave Chayka a leg up is his ability to handle media, especially the Toronto media, in one of the more difficult markets in the NHL.
“I mean, it’s a tough market to be in, as everyone knows, right? The media is diligent and there’s a lot of answering to the media. I hate that expression. I put that in quotes. But you’ve got to be able to stand up and speak about who you are,” explained Glasberg. “That’s the one thing just about John, not to give him the plug, but John is very smart and very good with the media. He tells it like it is. So, there’s no BS, there’s no trying to figure out what the message is. And I think that that was a huge, huge selling factor in terms of the proper fit.”
Glasberg also helped in the process of hiring Hiller as the team’s next head coach, but played more of behind the scenes role as Chayka and newly named Senior Executive Advisor of Hockey Operations Mats Sundin led that search.
The Maple Leafs will now join the rest of their summer off-season before training camp starts in September. Pre-season action begins on Sept. 19 with the season opener taking place in Toronto on Sept. 29 against the visiting Montreal Canadiens.
