Grading Darren Raddysh sign-and-trade between Maple Leafs, Lightning

The Toronto Maple Leafs and Tampa Bay Lightning connected on a sign-and-trade involving Darren Raddysh on Friday. The deal got close overnight and was confirmed in the morning, sending Raddysh to Toronto. After a career year, the Maple Leafs believe Raddysh can help their powerplay significantly. But did they overpay? Let’s take a look at the grades for both Raddysh and the new Toronto GM, John Chayka.

For Raddysh, this was an easy decision. Not only did he just sign a contract worth a guaranteed $68 million, but he gets to go home. Fans have dug up some of the defenseman’s old tweets, supporting the Leafs and even ragging on some former players. One gave Dion Phaneuf some blame for a 2013 loss, and he was far from the only one to sound that alarm. Raddysh gets to play for his hometown team, but did not take a discount to do it.

Before the 2025-26 season, Raddysh was a relatively anonymous defenseman on the Lightning’s back end. But he took over the powerplay when Victor Hedman went out, and dominated. Of his career-high 70 points last year, 26 came on the man advantage. Combine that with a weak free agency class, and Raddysh earned a lot of money this season.

According to Puckpedia, Raddysh has never made more than $1 million in a season. Now, he will earn $8.5 million each season for the next eight years. That alone shoots his grade up to the top of the class. Add in some of the elite offensive talent he will get to play with on the powerplay, and he gets even more credit. The concern for anyone is how Raddysh will do without Nikita Kucherov. But Auston Matthews isn’t a bad replacement.

Raddysh grade: A+

John Chayka’s first big swing as Maple Leafs GM

The Maple Leafs’ hiring of John Chayka as their next general manager was controversial, to say the least. In his lone attempt to run an NHL team, he cost the Arizona Coyotes draft picks and got himself suspended. His ban expired, but he was still not courted by any team. It was Toronto that called up the man running Tim Horton’s and Wendy’s locations across Canada to run a hockey team.

The Maple Leafs needed a new coach, so Chayka took the easy first move and fired Craig Berube. Then, he ran a lengthy search to land on Jim Hiller, who has a long history of running powerplays across the NHL. His first massive player acquisition was Raddysh, the breakout powerplay star of last season. There is no doubt that Chayka has targeted the man advantage as a place to improve.

That alone is not a bad thing, but the term and money it took to land Raddysh make it a poor move. Raddysh turns 31 next season, and his contract runs well beyond his prime. While the salary cap has gone up and $8.5 million is not what it once was, it still makes him one of the highest-paid defenders in the league. Targeting Raddysh wasn’t dumb, but this contract is baffling.

Raddysh, Alex Tuch, and Mason Marchment are among the players who will get eye-popping salaries this offseason. That alone doesn’t bring the team’s grade down. If Raddysh was the last player to add to Toronto’s championship puzzle, that would be one story. But they had the fifth-worst record in the league last year.

This will be a contract that weighs down the Maple Leafs’ salary cap for years. If it takes one dollar away from Auston Matthews, it’s an automatic F. But the math works out now where they could both be around, so the Leafs get a D+ for this move.

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