Since their appointment was announced on May 3, the new brain trust has completely gutted 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 caps a huge 59-day spell in his tenure, during which much of the squad received a much-needed facelift.
“Certainly, I think a player of Sergei Bobrovsky’s caliber sends a signal that we’re serious about moving this team forward and getting back on track and you know, trying to take it to another level,” Chaika said Wednesday night.
“I think if you look at the big 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 said there would be changes for the team, which missed the Stanley Cup playoffs for the first time since last season in 2016.
To their credit, whether their actions worked or not, they practiced what they preached.
When the Maple Leafs unexpectedly won the NHL Draft Lottery just 48 hours after Chayka and Sundin took over, it seemed to solidify the direction the franchise would be headed.
There will be no recovery.
Refurbishment only.
And it’s all thanks to a ping pong ball with the number 12 on it.
It turned out to be a lottery charm that gave the Maple Leafs a chance to select coveted forward Gavin McKenna with the No. 1 pick in the 2026 NHL Entry Draft in Buffalo on Friday.
The opportunity to acquire an NHL-ready prospect like McKenna was the catalyst for subsequent decisions to win now, especially with captain Auston Matthews only having two years left on his contract. This window management decided to go all in.
“We wanted to be the best team this year,” Chayka said.
Here’s how they’ve rebuilt the lineup over the past eight weeks.
Will appear (10): Bobrovsky, defenders Darren Radysh, Emil Andre; forwards McKenna, Nick Paul, Jack Roslovic, Colton Sissons, Teddy Blueger, Brandon Duhaime and Zach McEwen.
Out (7): Goalkeepers Joseph Wall, Dennis Hildeby, Samuel Ehrsson; defenders Brandon Carlo, Simon Benoit; forwards Matthias Macchelli, Nicholas Robertson.
That doesn’t include Jim Hiller replacing Craig Berube as coach.
The flurry of activity is causing a lot of anxiety.
Take, for example, Raddysh. The 30-year-old was acquired in a trade with the Tampa Bay Lightning on June 19 and is under contract for eight seasons, a risk for a player who has nearly doubled his career point total this season with 70 (22 goals, 48 assists) in 73 games after just 73 (13 goals, 60 assists) in 176 previous NHL games.
Then there’s Bobrovsky, who represents the biggest high-risk, high-reward bet of them all.
Firstly, he will be 38 years old when the 2026/27 season starts in September. However, his career-worst .877 save percentage last season with the Florida Panthers ranked 26th among 27 goalies with at least 40 starts, ahead of only Kevin Lankinen (.873) of the Vancouver Canucks.
Chaika does not seem to be bothered by these numbers. Looking through his blue-and-white glasses, he sees a competitor with an unrivaled work ethic who is on a mission to prove that he is one of, if not the best goalie in history (though players like Martin Brodeur, Dominik Hasek and Patrick Roy may have a say in that).
“Sergei is a game changer for us in terms of stability, consistency and longevity,” Chaika said. “Obviously the resume speaks for itself. He may well end up being the best of all time at the position. And to be able to provide 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 only on the ice, but certainly off the ice, with the mentorship, the professionalism, again, the championship reputation.”
“We thought about it from different angles. The total package made a lot of sense. And you always have your own opinion, but to actually be able to get a player of that caliber, you know he expects to win. I think it says a lot about the organization, it says a lot about the owner, and it also says a lot about the player and his leadership.”
Bobrovsky won back-to-back Stanley Cups with the Panthers in 2024 and 2025. He won the Vezina Trophy and was named a first-team NHL All-Star twice (2013, 2017) with the Columbus Blue Jackets.
Chayka even stated that there is no other goalie in the NHL that he would rather have when a team’s season is on the line.
“When we think about it, if we’re going to play Game 7, we think about goalies and how important that position is. In a position like that, is there another goalie in the world that we want to score on? And the answer is no,” he said. “We would have preferred to have Sergei Bobrovsky, and that was a big factor.”
In Toronto, Bobrovsky will reunite with Anthony Stolarz, his backup during the Panthers’ 2024 Cup run. His mentorship will also be demonstrated by American Hockey League playoff MVP Artur Akhtyamov of the Toronto Marlies, a 24-year-old player who grew up idolizing Bobrovsky.
When talking about all the trades that have been made since he joined the Maple Leafs, Chaika highlighted how the team’s spine has strengthened, which includes goaltenders, center defense and then the center position. At first glance this seems true.
Now the biggest question that remains is: Will McKenna give up No. 72, his longtime number dating back to his minor hockey days, in favor of Bobrovsky, who has hoisted the Cup multiple times with the same number on the back of his jersey?
It’s a dilemma that even the most die-hard Maple Leafs fans couldn’t imagine in late April.
Imagine being told then that McKenna and Bobrovsky would be playing for Toronto at the start of the 2026-27 season?
They wouldn’t believe you. Or on this team.
Now, thanks in part to the efforts of Chaika and Sundin, they are beginning to do so, even with the attendant risks.