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Maple Leafs' move for Darren Raddysh is first big risk of offseason

Defenseman Darren Raddysh. David Kirouac-Imagn Images

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Maple Leafs' move for Darren Raddysh is first big risk of NHL offseason

By Adam Gretz | Last updated Jun 19, 2026 7:50 PM ET

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The Toronto Maple Leafs are facing a massive offseason when it comes to the short-term and long-term outlook of their franchise. After shockingly missing the playoffs in 2025-26, the Maple Leafs completely cleaned house this offseason by firing general manager Brad Treliving and head coach Craig Berube, replacing them with John Chayka and Jim Hiller, respectively.

Now that new duo has to figure out how to rebuild a team that badly underachieved and has several holes all over its lineup.

Some lottery luck helped by giving them the No. 1 overall pick in this month's draft.

They also have a healthy amount of salary cap space to play with.

They started spending that cap space on Friday with a sign-and-trade deal that saw them acquire defenseman Darren Raddysh.

The Maple Leafs sent a fifth-round pick to the Tampa Bay Lightning for Raddysh's free agent rights, and then signed him to an eight-year, $68 million contract that carries the maximum term length (eight years) and an $8.5 million salary cap number per season.

It is the first major, blockbuster player move of the NHL offseason, and it is a massively risky move for the Maple Leafs.

Why Darren Raddysh is a risky move for Maple Leafs

On the surface, Raddysh makes a lot of sense for Toronto.

The Maple Leafs desperately need to upgrade their defense, and Raddysh was going to be one of the top players in a very thin and weak unrestricted free agent market.

He is also coming off a career year that saw him score 22 goals with 70 points in 73 games, making him one of the most productive defensemen in the NHL this past season.

Along with the production, he brings one of the league's hardest slap shots that could help add an entirely new dimension to their power play and open up more opportunities for that unit.

That's the good news.

So what's the downside?

Well, there are a few potential issues.

TRADE: We’ve acquired defenceman Darren Raddysh from the Tampa Bay Lightning in exchange for Toronto’s fifth-round selection in the 2026 NHL Draft
— Toronto Maple Leafs (@MapleLeafs) June 19, 2026

The first is that Raddysh is a late-bloomer when it comes to his stardom in the NHL, and did not become a full-time player until he was 27 years old. His age-27 and 28 seasons were solid, but nothing overly spectacular. It was not until this past season that he truly broke out in a contract year.

That is always a potential red flag.

Can he sustain that level of play again over another full season? And can he do it again outside of Tampa Bay's system? Especially now that he is going to be 30 years old when this new contract begins?

There is always a risk with long-term contracts in free agency because you are paying top dollar for players that have likely already played their best hockey for somebody else. The best-case scenario is that Raddysh gives Toronto three or four years of high-level play before his contract starts to become an albatross against the cap as he gets into his late mid-late 30s and starts to inevitably decline.

The worst-case scenario is that they find out his 2025-26 season was a fluke and he never comes close to that level of production again and they immediately regret it.

The only good news in that situation is that his contract is extremely front-loaded, so even though the salary cap hit remains consistent, the actual salary owed in the back half is significantly less. That could make it easier to move if needed.

The next big item on Toronto's offseason will be who they select with the No. 1 overall pick, and whether or not they trade young forward Matthew Knies for even more defensive help or more draft assets. Those two moves will also play a big role in what direction the team takes going into the 2026-27 NHL season.

Raddysh is a big-name start to the offseason. But the work is hardly done.

Adam Gretz

Adam Gretz is a freelance writer based in Pittsburgh. He covers the NHL, NFL, MLB and NBA. Baseball is his favorite sport -- he is nearly halfway through his goal of seeing a game in every MLB ballpark. Catch him on X @AGretz

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