Maple Leafs: A Week of Three Questionable Decisions

Charles-Alexis Brisebois
Maple Leafs: A Week of Three Questionable Decisions
Credit: Minas Panagiotakis/Getty Images

The Maple Leafs have been in the news this week—for several reasons.

And when you take the time to analyze it all, you realize that the three major decisions (the first ones made by John Chayka and Mats Sundin as club leaders) in recent days are… questionable.

We'll use that word instead of “controversial.”

On Tuesday, the Toronto Maple Leafs decided to trade Joseph Woll. We understand that the club wanted to free up space on its payroll (we'll come back to that), but it didn't go over well with the fans.

After all, the team has significantly weakened its goaltending. And since the organization clearly wants to continue competing, management couldn't afford to do that.

Then, the hiring of Jim Hiller as head coach two days ago also left fans wanting more. After all, he's a coach who has historically faced the same problem as his team: he struggles to get past the first round.

Yeah…

And just like that, overnight, the Maple Leafs managed to secure the services of Darren Raddysh. We might as well take the day off on July 1—there'll be nothing left… but that's another story.

He's expected to earn around $70 million—an eight-year deal averaging just under $9 million per year. He'll sign with Tampa Bay before the contract is traded for a late-round pick.

Raddysh would have become a free agent in two weeks. And let's just say he deserves a solid pay raise, considering he was making $975,000 in 2025–2026.

Have you ever seen a 30-year-old get a contract nine times bigger once he hit his thirties?

We can all agree that on the ice, the Maple Leafs will be better with Raddysh than without him in 2026–2027. No one doubts that, since he's a good defenseman.

But since when is ONE good season (out of nowhere) worth that much money?

(Credit: Hockey DB)

The Toronto native will be under a lot of pressure, and he's just gotten himself into a crazy situation. After all, the Maple Leafs' future doesn't look bright.

Auston Matthews might be on his way out… Morgan Reilly is expected to leave… the core is getting older and hasn't won anything… Max Domi is too injured to be ready for the start of next season…

A GM's job is to think long-term. And in the long run, when Raddysh starts to slow down (he's already 30) and the Maple Leafs haven't won anything with a core that's eventually going to fall apart, the new defenseman will be a liability.

He doesn't have great speed to begin with… what will he be like in four or five years?

The team needed to improve defensively, yet it let a good goaltender go to make room on the roster for an offensive defenseman who will never replicate his 2025–2026 season.

Instead of rebuilding right now, John Chayka went out and signed another contract that will tie everyone down in the medium term, when a rebuild becomes inevitable.


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You can't compare Lane Hutson's contract to that of the new Maple Leafs player because the Canadiens defenseman was far from full free agency at the time he signed.

But I'll say this: if Toronto knew how to develop defensemen, the team wouldn't need to overpay for guys like Darren Raddysh in their 30s.

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