It’s a go-for-it-now stage that you’d have to think will sit well with the team’s veterans, specifically Auston Matthews.
From the moment Chayka was named GM and Sundin senior executive adviser, hockey operations, on May 3, questions arose concerning how they would handle the situation surrounding the Maple Leafs captain moving forward. The 28-year-old center, who has two seasons remaining on the four-year, $53 million contract ($13.25 million average annual value) he signed Aug. 23, 2023, said in April, “I can’t really predict the future.”
Reading between the lines, it seemed apparent that Matthews had concerns that the team would not be competitive if its primary focus was stocking up on draft picks and prospects in order to contend several years down the road, not right away. As such, speculation arose that he might look to be moved to a contender if that was the master plan of the incoming management team.
In the 48 days that Chayka and Sundin have been on the job, the bold move to acquire Raddysh should be the best example to date of their mantra that the future is now. Chayka said as much when asked about the Matthews situation on June 5 while attending the 2026 NHL Scouting Combine in Buffalo.
“We’ve had several conversations with him and his representatives, and what I saw was a happy captain,” Chayka said at the time. “Someone who’s got a lot of pride to be the captain of the Toronto Maple Leafs. Someone who wants to win in Toronto, which aligns with how we’re thinking about it.”
Whether or not you agree with how they’re going about it, there’s no debating that they are being proactive, if not brash, in their quest to achieve that goal. It has, in fact, been a whirlwind.
Two days after the appointments of Chayka and Sundin, the Maple Leafs won the 2026 NHL Draft Lottery and now hold the No. 1 pick in the 2026 Upper Deck NHL Draft, being held June 26-27 at KeyBank Center in Buffalo. Penn State wing Gavin McKenna would seem to be the leading candidate to be selected by Toronto, with Swedish wing Ivar Stenberg also in the mix.
Coach Craig Berube was fired on May 13 and replaced Wednesday by Jim Hiller, an assistant with the Maple Leafs from 2015-19 who was on hand to help with the development of a then-young Matthews and William Nylander. Hiller also is known for his work on the power play and certainly will welcome the addition of the booming shot of Raddysh, who led NHL defensemen in power-play goals (10) this season.
When he was hired, Chayka immediately prioritized an improvement on defense for a Maple Leafs team that finished 31st in goals against (295) this season. Included in that: quicker puck movement out of the defensive zone, including better breakout passes.
On Tuesday, Toronto traded goalie Joseph Woll and defenseman Simon Benoit to the Philadelphia Flyers for goalie Samuel Ersson, defenseman Emil Andrae and a third-round pick in the 2026 draft. The key acquisition was Andrae, who fits into Hiller’s emphasis that skating is the most important part of a team.
Now comes Raddysh, who brings with him both offensive upside and, for that matter, accompanying questions.
