Raddysh move shows new Maple Leafs regime in win-now mode

TORONTO -- If ever there were any remaining doubts that the Toronto Maple Leafs are in win-now mode, they should be erased with the team’s acquisition of high-risk, high-reward defenseman Darren Raddysh on Friday.

You don’t add a veteran like this in a sign-and-trade with the Tampa Bay Lightning that comes with a new eight-year contract -- a deal that will see him be 38 years old when it expires -- if you are in a rebuild.

You don’t bring in a late bloomer like this who almost doubled his career point total this season, accruing 70 (22 goals, 48 assists) in 73 games after having just 73 (13 goals, 60 assists) in 176 previous NHL appearances, if you are looking toward the long-term future.

In essence, you don’t take such a big gamble like this, based on such a small body of work when it comes to a player’s individual success, if you are not all in.

Which the Maple Leafs’ new management team of John Chayka and Mats Sundin is quickly showing it is, all the while without fear that its wager might implode into a giant blue-and-white disaster.

"I think the part of the value that we were most focused on was his ability to impact the game," Chayka, the Maple Leafs general manager, said of Raddysh on Friday afternoon, adding that "he’s a player that plays up against top competition and does quite well. He's a player that breaks the puck out well, he's a player that can join the rush and supplement offense, transitions well, defends the blue line well. 

“You start adding up all the elements that go into the end result of good production and kind of the robust play of all that, (and it) gave us a lot of confidence that we're getting a defenseman that we haven't had in this organization for a long time.

“For us it's an aggressive move. It's not without risk, of course, but we just felt that, given the stage we're at, and what he brings to the table, felt it was worth pursuing.”

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.

On one hand, when it comes to his impressive numbers, it would be naive not to take notice that Lightning forward Nikita Kucherov, the recent recipient of the Hart Trophy as NHL MVP this season, had the primary assist on nine of Raddysh’s 10 power-play goals and assisted on 15 of his 22 goals altogether. He’s the type of elite talent that made those around him like Raddysh better, although Matthews and Nylander will be the foundation of a respectable supporting cast for him in Toronto.

Of more concern should be the age of the Toronto blue line, yet another sign that management believes the window of winning is now. Five defensemen -- Raddysh (30), Jake McCabe (32), Oliver Ekman-Larsson (34), Morgan Rielly (32) and Chris Tanev (36) -- are 30 or older.

That doesn’t mean the Maple Leafs are done remaking the roster. Far from it.

“We continue to evaluate the market to see how we can best shape our ‘D’ for the next year,” Chayka said. “But as we sit here today, with Darren as part of that and, you know, hopefully some better health from some veteran players, we think it’s a pretty good group, and a group that’s getting a chance.

“But again, it’s one thing we continue to evaluate.”

There was plenty of head scratching around the hockey world with the hiring of Chayka, who hadn’t held a position of control in the NHL since quitting as GM and president of hockey operations of the Arizona Coyotes on July 26, 2020. There was more of it when Hiller was brought in ahead of more splashy names like Patrick Roy. And the second-guessing continued in this market with the addition of Raddysh, not because of his potential influence this upcoming season, but because of the long-term commitment the team made in what some believe is an unproven commodity.

This much is certain: In less than two months on the job, Chayka has shown he’s not shy to pursue assets he wants, whether the outside world thinks it's worth it or not. That’s why he wasn’t willing to wait for Raddysh to hit free agency July 1, instead choosing to go after him via the trade route in what he refers to as the team’s offseason priority.

“Obviously Darren, with his background, being the top potential free agent, we feel very strongly about our Plan A,” he said. “It came together pretty quickly but the opportunity, in our opinion, to secure the top free agent, is an organization win.”

For his part, Raddysh is no stranger to the hockey fishbowl that is Toronto. He’s from Caledon, Ontario, about 40 miles northwest of Scotiabank Arena, and played minor hockey with the likes of Connor McDavid and Sam Bennett. Most importantly, he chose to forgo free agency and agreed to the move to come back to southern Ontario, contrasting the growing narrative that players don’t want to come here because of the omnipresent spotlight. 

For Raddysh, it’s a hockey homecoming.

For the suddenly throw-caution-to-the-wind Maple Leafs, it’s an iffy short-term wager they’re willing to make.