It's Hard Not to Root for the Maple Leafs, Darren Raddysh

2 min read• Published September 13, 2026 at 5:04 p.m.
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There are plenty of ways to describe Darren Raddysh becoming a $68-million Maple Leaf. The simplest way to put it is this: nobody saw it coming. Not Raddysh himself, exactly. He always believed he could play. But there was a time when other people had pretty much stopped believing it for him. In his fifth professional season, playing in Hartford, Raddysh found himself having conversations he never expected to have. Was hockey really going to be his career? Was this the right path? Where was all this going?

Those are pretty serious questions for a 25-year-old hockey player. They are also the kind of questions that can make a person look honestly at himself.

Related: The Maple Leafs May Spend October Figuring Out What They Have.

Raddysh took a long, honest look at his career. And then he kept playing.

That is the part of this story that makes the Maple Leafs' decision to give him an eight-year, $68-million contract so fascinating. The money is enormous. The expectations will be enormous. But the journey to get there is almost more interesting than the contract itself.

Raddysh wasn't drafted. He wasn't some highly touted prospect whose NHL arrival was simply delayed. He spent years trying to convince people he belonged. He played in the AHL. He moved between organizations. The Blackhawks moved on from him. The Rangers moved on from him. And still, he kept going. There is something wonderfully stubborn about that.

Eventually, the Tampa Bay Lightning gave him the opportunity he had been waiting for. Last season, he finally got his first big NHL chance and made something of it. He scored 22 goals and put up 70 points, numbers that suddenly made everybody notice the player who had been there all along.

Now Raddysh is a Maple Leaf, and he's making $8.5 million a season.

Think about that for a moment. The man who once wondered whether hockey would be his career will make more in one season than he earned during his first nine professional seasons combined. That's quite a turnaround.

Maybe the best lesson in the Raddysh story isn't about perseverance, although there is plenty of that. It's about the danger of deciding too early what somebody can become. Raddysh was overlooked for years. He wasn't flashy enough. He wasn't considered a prospect. He wasn't a great skater. The hockey world had essentially placed a label on him.

He just refused to believe it. And now, at 30, Darren Raddysh is finally getting the opportunity he spent a decade chasing.

Funny thing about hockey. Sometimes the long way turns out to be the right way.

Related: The Maple Leafs Have a Different Kind of Problem This Season