The risk in signing Raddysh
There’s often a warning label in free agency that comes with paying a player for what they’ve already done rather than what they could be capable of. Critics of this contract will tell you that the Maple Leafs should have prioritized finding the next Darren Raddysh and letting somebody pay the price for his best seasons, and because of how much of a late-bloomer Raddysh is, the Leafs would not want to find themselves in a situation where they’re stuck paying him north of $8 million annually if he’s going to regress to the mean and hover around the 40-point mark instead. If that happens, it’s going to be a cap nightmare for the Leafs, and one that could interfere with their abilities to extend young future core pieces including Easton Cowan, Ben Danford, and their upcoming first-overall pick (presumably Gavin McKenna).
Why it’s worth it for the Maple Leafs
There is one thing and one thing only that matters to Leafs fans and their city – winning a Stanley Cup. With Auston Matthews and William Nylander both creeping up on their 30s and still without even a Conference Final appearance, we’re well past the days where worrying about the future trumps the expectations of the present. The Leafs have underperformed more than any other team over the past decade, partially due to bad luck but mostly due to a tendency to disappear in important playoff games. At this point, the bar is a Stanley Cup, and they won’t be earning any props for making a Conference Final or even making the Cup Final.
Darren Raddysh, acquired and signed 8x$8ishM by TOR, is a top-pair offensive defenceman with an old school clap-bomb from the point, strong puck-moving all over the ice, and solid stick-work defensively. #LeafsForever
There’s also a legitimate argument to be made that we would have seen Raddysh’s breakout season happen sooner if he wasn’t stuck behind Victor Hedman for two years. Hedman only played 33 games for the Lightning last season, which freed up a spot on the Lightning’s top power play unit and also opened the door to more ice time at 5-on-5. His Corsi rating hovered just above 50% in both 2024-25 and 2023-24, and had the third-highest expected-goals percentage on the Lightning in 2023-24.
In the end, the Raddysh trade and subsequent signing is the exact type of big swing the Leafs need right now. Brad Treliving was a very conservative general manager – he only made two trades in his first eight months on the job with the Leafs and they both involved depth players. The Leafs were also one of the worst puck-possession teams by a long shot in 2025-26, and you don’t need analytics to tell you that they couldn’t make a breakout pass last season. Signing Raddysh addresses both of these issues, and it took Chayka one month to address an issue that the Leafs struggled to figure out while Treliving was here.
Will this contract look terrible in six years? Possibly. Does it matter right now? Absolutely not. They’ve needed a player like this on their back end for a long time, and while nobody should be planning any parades on the basis of this signing alone, signing him gets them closer to where they need to be. If the Leafs don’t win in the next couple of years, then they’re likely headed for a rebuild regardless. If they do win, nobody is going to be saying “yeah you won a Cup but that contract is gonna be really hard to move”.
If nothing else, this move shows that the Leafs are well aware of what went wrong last season and what they need to do to fix it. And if the Leafs can get a 60+ point defenceman with a howitzer from the point that can help revolutionize a stagnant power play, then the gamble will be worth it all day.