3 Maple Leafs Deals with the Best Odds of Going Sideways – The Hockey Writers – Toronto Maple Leafs

The Toronto Maple Leafs are in a good position when it comes to their contracts. Having gotten ahead of the recent spike in salaries, only a couple of the organization’s signings appear to be the team paying full freight and not getting a team-friendly deal.

If we look at some of those contracts, what are the chances these deals look bad in hindsight? How many of them have a real chance to go sideways?

Sergei Bobrovsky – $21 Million

The big gamble this summer was Toronto revamping their goaltending situation and going with an aging veteran who was coming off a down season. Sergei Bobrovsky got a three-year deal with Toronto with an AAV of $7 million. It was a good chunk of change and some term for a 37-year-old. This was a goaltender the Florida Panthers decided to move on from, despite his taking them to two Stanley Cup championships in back-to-back seasons.

Do the Panthers know something the Maple Leafs don’t? Perhaps, and if so, there’s a chance that Toronto finds out the hard way that Bobrovsky’s game is only going to go downhill from here.

This isn’t just about potentially adding a Hall of Famer whose best days are behind him. It’s that the Leafs moved on from both Joseph Woll and Dennis Hidleby to make this change. Leaving the Leafs with Bobrovsky and Anthony Stolarz is a gamble.

Jack Roslovic – $8 Million

Coming off a strong regular season with the Edmonton Oilers, Jack Roslovic did what he does and practically disappeared in the playoffs. The knock on him is that he’s not a big-game player and that he crumbles when the stakes are higher. Skilled but soft, there’s a good chance he provides scoring for Toronto, but vanishes when they need him most.

And while $4 million per season isn’t a huge chunk of change, it’s not the $1.5 million the Oilers signed him to last season. Will he provide the depth scoring Toronto wants and needs? Or, will he continue to be inconsistent and unreliable on the defensive side of the ice?

Darren Raddysh – $68 Million

The home run swing was defenseman Darren Raddysh. Locked in on him from the outset of free agency, the Maple Leafs decided to get an early jump and traded for him, with an eight-year extension in the bag. The $8.5 million seems fair given the 22 goals and 70 points he put up in 2025-26. However, it was the only time he’d ever come close to that kind of production.

Raddysh’s previous high was 37 points, and the Maple Leafs are banking that what he brought last year in Tampa when given the opportunity is what he’ll be able to do again and again. He’d better be, because eight years is a long time.

If his big season was his one and only, the Leafs just guaranteed a ton of money to a player who arguably didn’t have the track record to deserve it.

Will These Deals Bite the Maple Leafs?

As many teams do in free agency, the Maple Leafs have taken some risk here. Bobrovsky was among the best of the best for some time. Is he now? It didn’t appear that way from last season’s play. Jack Roslovic has skill, but will he crack under the pressure? Raddysh looks like he might have broken out last season, but what if that one season was a bit of a fluke where every single condition was right?

It’s almost $100 million in contracts Maple Leafs GM John Chayka handed out. This season will tell us if he spent the money wisely.