TORONTO — Toronto Maple Leafs icons Doug Gilmour, Darcy Tucker, and Wendel Clark all sat front row, stage left.

Stage right sat Kathryn Chayka and her three young children — Capri, Monterey, and Steel — all decked out in small, box-fresh CHAYKA Leafs road sweaters, all gripping Carlton the Bear stuffies and looking up at Dad.

Dad would be John Chayka, once the youngest general manager in NHL history and today the latest GM charged with ending the drought in Toronto.

“At the end of the day, this is the most important decision that I will likely make in my tenure at MLSE,” CEO Keith Pelley had predicted.

Pelley landed on the Ontario-born Chayka and Legends Row icon Mats Sundin, who has moved his family from Stockholm to “the hockey capital of the world” (Sundin’s words).

From a Q&A on a Real Sports dais, separate scrums off-camera, an eavesdrop on a 32 Thoughts: The Podcast recording, and our own one-on-one chat with the new GM, here is what we learned about the relationship, the challenge, and where Sundin and Chayka stand on the roster…

Chayka described his hiring as “both an exhaustive and frankly exhausting process,” as he survived a series of interviews with different people and different formats.

Pelley said he spoke with 27 people about the job opening before landing on his one-two punch. Neil Glasberg of The Coaches Agency, Pelley said, did not have a vote but facilitated meetings with a slew of candidates.

The CEO also stressed that he conducted his “due diligence” on Chayka, whose Coyotes tenure included illegal testing of prospects and ended ugly, when the GM sought employment elsewhere without approval.

Pelley also shot down a rumour that Chayka was a client of Glasberg’s and that Leafs alumnus Tie Domi was involved in the process “whatsoever.”

Domi is, however, the link between Chayka and Sundin’s personal relationship. The two men met in London, through Tie, watching Max Domi’s Knights compete for a Memorial Cup while Chayka was a budding star at Western’s Ivey Business School.

“I’ve watched a lot of hockey with Tie, and I’ve been very fortunate to come across a lot of NHL players, ex-players, managers, coaches that I feel very fortunate to have learned from,” said Chayka, who speaks with Tie monthly.

“I didn’t play in the NHL. So, to understand from someone who’s done it, their perspective, the locker room perspective, the players’ mindset, it’s been incredibly valuable for me. And Tie is one of hundreds of people that I’ve learned from.”

That Chayka, as GM, and Sundin, as senior executive adviser of hockey operations, were unveiled as a team keeps the power structure vague.

Chayka is running hockey operations, yet he doesn’t view himself above Sundin.

“The best idea should win. And if that’s my idea, that’s great. But oftentimes it’s not going to be. And if it is, we got a problem,” said Chayka, who anticipates Sundin to wield a big voice in shaping the team.

Pelley desires a collaborative approach on everything.

“In fact, I don’t even think Mats knew what his contract title was until he got the contract himself,” Pelley said. “I can tell you, unequivocally, that these two gentlemen are totally focused on one thing, and that is bringing the Stanley Cup to Toronto.

“The chemistry they have is phenomenal. I think we’re in for a real treat.”

OK. So, what if Chayka has an idea that Sundin doesn’t like?

“We don’t do it,” Chayka said. “That simple.”

Auston Matthews has been noncommittal on his desire to play out the final two seasons of his contract.

“He holds a big stake in everything we do, and I want to go and listen and hear what he has to say,” Chayka said.

The former Coyotes GM has known Matthews, his family, and his agent, Judd Moldaver, since his time in Arizona. But now their relationship changes.

That connection starts anew with the shared goal of winning a Stanley Cup.

Sundin and Chayka will meet with Matthews over the next couple of weeks. They’ll make a pitch explaining Toronto’s competitive window is still open and propose a plan to bounce back from 2025-26’s disappointment.

Just as important: They will listen to the player’s thoughts on the state of the team.

“That’ll kind of help sculpt our vision a bit as well,” Chayka said. “I think he deserves some answers about where we’re at and where we’re headed, and give him a forum to provide feedback and ask questions.”

Chayka said the Coyotes spent their entire existence searching for a defensively responsible goal scorer at centre. He’s not about to let one walk out of Toronto without a fight.

“We are incredibly fortunate to have Auston. It is our job to sell him on what we are capable of in terms of reaching the ultimate goal. I know that is what is most important to him,” Chayka said.

“How we do that is not a sales job. It is more about what the vision is, what the plan is, and what concrete steps we’re going to take to get the team to where he wants it to be.”

Added Sundin, who passed the franchise goal-scoring crown to Matthews midseason: “It’s very fortunate to have a player of that calibre. And let’s hope that he’s committed to lead this team and through the next period as well.”

Chayka spoke on the phone with Craig Berube Sunday night and plans to sit down face-to-face with his inherited head coach and Sundin this week to pick Berube’s brain on what worked and what didn’t with the current roster.

The GM is open to retaining Berube, who has two more seasons on his contract.

“It’s hard to find great coaches. He’s a great coach. I was lucky to work with Rick Tocchet in Arizona. Obviously, there’s a deep friendship there, and I think they share notes and ideas on things. So, I’m not starting from zero,” Chayka said.

“I think he is a tremendous coach, a Stanley Cup coach, and a good person.”

Sundin and Chayka both identified Toronto’s blue line as an area in need of improvement. The Maple Leafs allowed 3.6 goals per game this season, more than any team in the conference.

“The way the team breaks the puck out, the way they defend, the way they move through the neutral zone, I think there needs to be a change of the mix. Or change the strategy,” Chayka said.

“Adding to the defence corps is a priority. I don’t have a crystal ball. We’ll see what the options are as they come available. But we intend on being aggressive there.”

That will demand creativity, however. Toronto’s top seven defencemen are all under contract for 2026-27, and five of them have trade protection.

“Flexibility is a real asset, and obviously we don’t have that in that position. I think we’re gonna have to make some decisions and see how we can create some flexibility. But I’m aware that they’re under contract. And again, it’s a priority for us to try to find a way to improve it.”

The biggest wow to emerge from Brad Treliving’s final trade deadline as Leafs GM was that he explored the possibility of a Matthew Knies trade.

Knies has it all — youth, size, skill, cost certainty. What he does not have is any trade protection. But Knies does have two new sets of eyes on his situation.

“Matthew Knies is like a really unique player. I think his blend of size and skating and skill is really, really hard to find,” Chayka said. “I’m not aware of what happened at the deadline or what previous regimes thought. I think Mats and I are going to go through and evaluate the roster and make some decisions.

“Ultimately, if you’re making a decision, you’re trying to get better. I think you’d be really hard-pressed to do better than Matthew Knies.”

Everyone at Monday’s podium was careful not to place a timeline on success. Chayka would not commit to a season by which he envisions the Maple Leafs as a Cup contender, nor would he promise playoffs in 2027.

The executive is smart enough to keep expectations low as he reshapes an aging roster in a speeding division.

“The optimistic, hopeful side is that this team has a lot of latent upside. A lot of the players underperformed. I think there is a lot of opportunity to get in there and find ways to do a better job with the internal group,” Chayka said.

The front office knows it must hit on trades and free agents as well as get healthy bounce-back campaigns from core pieces like Matthews and Chris Tanev.

“I just think there’s no margin for error in this market to get the ultimate job done,” Chayka said.

“Talking to some of the scouts already, there’s a belief that we can get some momentum back in this group. And I think momentum is a funny thing in sports. If we can do that, I think it’ll take care of itself.”