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The Darren Raddysh Deal Is Risky — But It’s Exactly the Move the Leafs Needed to Make: Leafs Morning Take
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Nick Alberga
Jun 19, 2026, 13:30 EDTUpdated: Jun 19, 2026, 12:53 EDT
John Chayka isn’t messing around.
After trading Joseph Woll and Simon Benoit to Philadelphia and hiring Jim Hiller as head coach, the Maple Leafs were back in the headlines on Friday morning, completing a sign-and-trade with the Tampa Bay Lightning for Toronto native Darren Raddysh.
Naturally, that’s where the conversation started on the Friday edition of Leafs Morning Take. The timing couldn’t have been better, either, with NHL insider David Pagnotta filling in for Jay Rosehill as co-host.
As mentioned, it’s been a busy week for the Maple Leafs, and truthfully, it feels like it’s only going to continue—even after this bombshell move. Toronto sent a 2026 fifth-round pick in exchange for Raddysh’s rights, allowing them to sign the 30-year-old defenceman to an eight-year contract. In total, the deal is worth $68 million, carrying an average annual value of $8.5 million. Without question, there’s risk attached to a contract like this. That said, it’s the type of swing the Leafs desperately needed to take. If you’re going to reshape the roster and try to change the trajectory of the organization, sometimes you have to be willing to bet big.
After that, we recapped Game 4 of the Calder Cup Final a bit. Unfortunately, the Marlies blew a 3-1 third period lead and fell 4-3 in OT against Chicago. That said, they’re still up 3-1 in the series. Game 5 goes tonight —also in Toronto.
After we discussed what the Leafs could potentially do next, Dennis Bernstein stopped by to break down the Raddysh news, and he was firmly in favour of the move. Bernstein said the contract didn’t surprise him at all, adding that he believes it’s fair value for a player who could produce around 15 goals and 65 points annually. The longtime Los Angeles based broadcaster and writer also weighed in on Morgan Rielly’s future, suggesting Anaheim as a potential landing spot, while agreeing that moving Matthew Knies would make little sense unless the Leafs were blown away by a king’s ransom offer. To wrap things up, Bernstein shared his thoughts on the hiring of Jim Hiller, admitting he was surprised by the decision and still has plenty of questions about how the fit will work in Toronto.
What a week it’s been. There was no shortage of talking points, and something tells me we’re only getting started. As always, whatever happens—and whenever it happens—we’ll have you covered. Enjoy the weekend, and be sure to join us on Monday as we kick off draft week and continue breaking down what’s shaping up to be a fascinating offseason for the Maple Leafs.
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