3 Maple Leafs Deal With Best Sideline Prospects – Hockey Writers –

The Toronto Maple Leafs are in good shape when it comes to their contracts. Having passed on recent salary increases, only a few of the union’s signees appear to be full-payers and do not receive collective bargaining agreements.

Looking at some of those contracts, what are the chances that these deals will look bad in retrospect? How many of them have a real chance to go sideways?

Sergey Bobrovsky – $21 Million

The big gamble this summer was Toronto revamping their offensive line and moving with an aging veteran who was coming off a down season. Sergey Bobrovsky received a three-year deal with Toronto with an AAV of $7 million. It’s been a good turnaround and some form for the 37-year-old. This was the goaltender the Florida Panthers decided to move on to, despite taking them to two Stanley Cup championships in consecutive seasons.

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

This isn’t just about adding a Hall of Famer whose best days are behind him. 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 season with the Edmonton Oilers, Jack Roslovic did what he did and disappeared from the playoffs. What strikes him is that he is not a great player and collapses when the number is high. Skilled but soft, there’s a good chance he’ll provide points for Toronto, but disappear 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 for last season. Will he provide the scoring depth Toronto wants and needs? Or, will he continue to be inconsistent and unreliable on the defensive end of the ice?

Darren Raddysh – $68 Million

The home run hit was infielder Darren Raddysh. Locked in from the start of free agency, the Maple Leafs decided to jump early and trade him, with an eight-year extension in the bag. $8.5 million seems about right considering the 22 goals and 70 points he put up in 2025-26. However, it was the only time he came 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 will be able to do again and again. They better be, because eight years is a long time.

If his big season was his alone, the Leafs guaranteed a ton of money for a player who didn’t have the record he deserved.

Will These Deals Bite Maple Leaves?

As most teams do in free agency, the Maple Leafs took a risk here. Bobrovsky was one of the best for a long time. Is it now? It didn’t look like that in the game last season. Jack Roslovic is talented, but will he crack under pressure? Raddysh looks like he might have come off last season, but what if that one season was a mess when all the conditions were right?

Nearly $100 million in Maple Leafs John Chayka’s contracts have not been awarded. This season will tell us that you spent the money wisely.