Since the announcement of their respective hirings was made on May 3, the incoming braintrust has completely shredded the roster as part of a much-needed new look led by two-time Stanley Cup-winning goaltender Sergei Bobrovsky. The signing of the 37-year-old Wednesday capped off a huge 59-day span on the job in which a significant chunk of the franchise has received a much-needed face lift.
“Certainly a player of Sergei Bobrovsky’s caliber, I think, sends a message that we're serious about moving this team ahead and getting back on track, and you know, trying to take it to another level,” Chayka said Wednesday night.
“I think if you look at the full picture, we're a much more dynamic team today than we were 24 hours ago,” he added.
Not to mention eight weeks ago.
That’s when Chayka and Sundin came in vowing there’d be change for a team that missed the Stanley Cup Playoffs for the first time since 2016 last season.
You’ve got to hand it to them: Whether their moves inevitably work or not, they’ve practiced what they preached.
When the Maple Leafs surprisingly won the NHL Draft Lottery just 48 hours after Chayka and Sundin took over, it seemed to solidify the direction the franchise would head in.
There would be no rebuild.
Only a retool.
All thanks to a ping pong ball with a No. 12 on it.
It proved to be the lucky charm in the lottery that gave the Maple Leafs the chance to select highly coveted forward Gavin McKenna No. 1 at the 2026 NHL Draft in Buffalo on Friday.
The opportunity to land an NHL-ready prospect like McKenna was a catalyst for ensuing decisions to win now, especially with captain Auston Matthews having just two years remaining on his contract. It’s a window management has decided to go all in on.
“We wanted to be the best possible team we could for this year,” Chayka said.
Here’s how they’ve reconstructed the roster in the past eight weeks.
Coming in (10): Bobrovsky, defensemen Darren Raddysh, Emil Andrae; forwards McKenna, Nick Paul, Jack Roslovic, Colton Sissons, Teddy Blueger, Brandon Duhaime and Zack MacEwen.
Heading out (7): Goalies Joseph Woll, Dennis Hildeby, Samuel Ersson; defensemen Brandon Carlo, Simon Benoit; forwards Matias Maccelli, Nicholas Robertson.
That’s not including the replacing of Craig Berube with Jim Hiller as coach.
The flurry of activity comes with plenty of concern.
Take Raddysh, for example. The 30-year-old was acquired in a sign-and-trade with the Tampa Bay Lightning on June 19 and is under contract for eight seasons, a gamble for a player who almost doubled his career point total this season with 70 (22 goals, 48 assists) in 73 games after having just 73 (13 goals, 60 assists) in 176 previous NHL games.
Then there’s Bobrovsky, who is the biggest high-risk, high-reward wager of them all.
First off, he’ll be 38 years old when the 2026-27 season kicks off in September. All the while, his career-worst .877 save percentage last season with the Florida Panthers ranked 26th among the 27 goaltenders who started at least 40 games, topping only Kevin Lankinen (.873) of the Vancouver Canucks.
Chayka seems unfazed by those numbers. Looking through his blue-and-white-colored glasses, he sees a competitor with an unequaled work ethic who is on a mission to prove he’s one of, if not the top goalie, in history (although the likes of Martin Brodeur, Dominik Hasek and Patrick Roy might have a say in that).
“Sergei is a real game-changer for us in terms of the stability, the consistency, the durability,” Chayka said. “Obviously, the resume speaks for itself. He could possibly end up being the best in that position of all time. And to be able to secure a player like that for this team that's looking to break through, we feel like it was the right player at the right time, not just on the ice, but certainly off the ice, with the mentorship, the professionalism, again the championship pedigree.
“We thought about it from all different angles. The full package just made a lot of sense. And you always have your own opinions, but to actually be able to land a player of that caliber, you know, he's looking to win. I think it says a lot about the organization, says a lot about the ownership, and a lot about the player and the player’s leadership.”
Bobrovsky captured back-to-back Stanley Cup championships as a member of the Panthers in 2024 and 2025. He has won the Vezina Trophy and earned NHL First Team All Star recognition on two occasions (2013, 2017) as a member of the Columbus Blue Jackets.
Chayka went as far as to say there is no other goalie in the NHL he’d rather have when a team’s season is on the line.
“As we think about it, if we're going into a Game 7, we're thinking about goalies and how important that position is. In a position like that, is there another goalie in the world that we'd want a net for us? And the answer would be no,” he said. “We'd prefer to have Sergei Bobrovsky, and that was a big part of it.”
In Toronto, Bobrovsky will be reunited with Anthony Stolarz, his backup during the Panthers’ Cup run of 2024. His mentorship will also be on display with American Hockey League playoff MVP Artur Akhtyamov of the Toronto Marlies, the 24-year-old who grew up idolizing Bobrovsky.
When talking about all the transactions that have been made since he joined the Maple Leafs, Chayka stressed how the “spine” of the team -- which incorporates the goalies, up the middle on defense, then the center-ice position — has been strengthened. At first blush, it seems to be a valid point.
Now the biggest question that remains: Will McKenna give up No. 72, his long-time number dating back to his minor hockey days, to Bobrovsky, who’s hoisted the Cup on multiple occasions with that same number on the back of his jersey?
It’s a dilemma even the most diehard of Maple Leafs fans could not have imagined in late April.
Imagine telling them at that time that McKenna and Bobrovsky would be playing for Toronto at the start of the 2026-27 season?
They would not have believed you. Or in this team.
Now, thanks in part to the efforts of Chayka and Sundin, they are starting to, even with the accompanying risk.
