The Toronto Maple Leafs aren’t done shaking things up just yet. Hours after shipping Joseph Woll and Simon Benoit to Philadelphia, the team is reportedly working behind the scenes on a sign-and-trade that would bring defenseman Darren Raddysh into the fold.
NHL insider Elliotte Friedman dropped the news late Wednesday night, saying Toronto and the Tampa Bay Lightning are hashing out the framework of a deal for the 30-year-old pending unrestricted free agent. The full return details and contract numbers haven’t surfaced yet, but Friedman expects it to come together by morning.
Raddysh just wrapped up a career year in 2025-26. He put up 22 goals and 70 points from the blue line, which is the kind of production that makes teams pay attention even if he’s not a household name. For a Leafs team that’s been looking for depth on the back end and maybe another right-handed shot on the power play, Raddysh fits a need.
This is where it gets a little tricky. Because Raddysh is an unrestricted free agent, the Leafs can’t just trade for his rights the normal way. That’s where the sign-and-trade structure comes in. Tampa essentially lets Toronto negotiate a fresh contract, then executes the trade after the new deal is signed. It’s a common workaround in the NHL to help teams manage cap space while still getting value for a player they’re about to lose for nothing.
The Lightning are in a tight spot cap-wise — they always are these days — and Raddysh probably priced himself out of their range after that breakout season. So instead of letting him walk July 1 for zero return, they’re working with Toronto to squeeze something out of it. Smart business, even if it means watching a guy go to a division rival.
Toronto’s front office has been aggressive this offseason. Trading Woll and Benoit was already a notable shift, clearing cap room and signaling they’re willing to move pieces most fans assumed were part of the core. Adding Raddysh would give the Leafs another puck-moving option and a guy who can eat minutes. He averaged over 22 minutes a night last season and showed he can drive offense from the point.
So what’s the hold up? Probably just finalizing the contract length and AAV, plus whatever Tampa gets back in the swap. It could be a draft pick, a prospect, or a roster player. Friedman didn’t specify, and the teams haven’t confirmed anything publicly yet.
This is a developing situation. Expect more details to leak out once the ink dries.
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