The Toronto Maple Leafs have put themselves in a solid spot with their contracts, at least on paper. By getting ahead of the recent rise in salaries, most of the organization’s signings don’t look like the kind of deals that will haunt them later. But a few of them carry real downside if things turn the wrong way.
The biggest swing came in goal. Toronto overhauled its goaltending and bet on Sergei Bobrovsky, a 37-year-old coming off a down season, on a three-year deal worth $7 million annually. That’s a hefty price for a veteran at that stage of his career, especially after the Florida Panthers moved on from him even though he helped them win two Stanley Cup championships in back-to-back seasons.
That alone makes the deal worth watching. If Florida knew something Toronto doesn’t, the Leafs could end up learning the hard way that Bobrovsky’s best hockey is already behind him.
And this isn’t just about age or decline. Toronto also moved on from both Joseph Woll and Dennis Hidleby to make the change, leaving Bobrovsky and Anthony Stolarz as the tandem.
That’s a gamble.
Jack Roslovic is another contract that could swing either way. He comes to Toronto after a strong regular season with the Edmonton Oilers, but the playoff version of Roslovic is a different story.
The criticism has followed him for a while: plenty of skill, but not much evidence that he delivers when the games matter most. He can score, sure, but there’s a real question about whether he disappears when the pressure rises.
At $4 million per season, Roslovic isn’t an outrageous investment. Still, that’s a noticeable jump from the $1.5 million the Oilers gave him last season. Toronto is banking on depth scoring, but it also has to hope he stays consistent and holds up defensively.
Then there’s the biggest commitment of the bunch: Darren Raddysh. Toronto made him a priority early in free agency, traded for him, and already had an eight-year extension ready to go. The $8.5 million average annual value looks reasonable on the surface after he posted 22 goals and 70 points in 2025-26.
The problem is that production was new territory for him. Before that, his career high was 37 points.
The Maple Leafs are betting that last season in Tampa was the real version of Raddysh, the one that finally got a full runway and delivered. If that was the outlier instead, Toronto just locked in a massive deal for a player who didn’t have much of a track record to support it.
So yes, there’s risk here. Bobrovsky is the aging veteran gamble.
Roslovic is the streaky scorer who has to show up when it counts. Raddysh is the big-money bet on a breakout season that may or may not be repeatable.
Altogether, John Chayka handed out nearly $100 million in contracts. Whether those deals age well will come down to this season.
In Other News...
Canadiens Rumors Just Put The Leafs In A Brutal Spot
The chatter around John Tavares comes at a tricky time for Toronto, because the Maple Leafs still view him as a valuable center and have not lined up an obvious answer if his name keeps surfacing in trade talk. Montreals reported interest only adds to the pressure, since any serious discussion involving a player of Tavares stature would force Toronto to weigh present-day value against a future without much certainty down the middle.
For the Leafs, the problem is not just what Tavares means on the ice, but how thin the fallback plan looks if things ever moved beyond speculation. The organization would need to sort through replacement options and decide whether the return could justify opening that hole in the lineup, which is why this kind of rumor always lands with extra force in Toronto. [Read more 🡒]
Maple Leafs May Have Misread A Marner Replacement All Along
Matias Maccelli arrived in Toronto as a low-cost swing for a team always looking for another layer of skill, but his role never really matched the upside that made the move interesting in the first place. The Maple Leafs brought him in from Utah for a third-round pick, then mostly parked him in the bottom six, a usage pattern that left little room for him to show whether he could be more than a depth piece in a lineup built around Auston Matthews and the top six.
Even so, there were brief signs that Maccelli could still help a team with more room for offense. He spent only 92:34 alongside Matthews across 49 games, and after the Olympic break he put up 7 goals and 14 points, the kind of stretch that suggests there may have been more to unlock with better deployment. Instead, Toronto moved on, and the question now is whether the Leafs simply never gave him the runway to become the kind of complementary scorer they were hoping to find. [Read more 🡒]
Maple Leafs May Be Ignoring Their Best Auston Matthews Fix
A familiar Maple Leafs puzzle is back in focus, and it starts with Auston Matthews and William Nylander. The two have already shown they can drive play together, and the idea of putting Nylander back on Matthews left side has real appeal for a team still searching for the right mix around its captain. Torontos offense has often looked its best when those two are on the same page, and the case for revisiting that pairing is easy to understand.
The bigger question is what comes next on the other wing, because the Leafs still have not settled on a proven top-six right winger this offseason. Jack Roslovic is part of the conversation, helped by his previous time alongside Matthews and the fact that the fit was encouraging enough to merit another look. If Toronto can keep the defensive structure intact, a Matthews-Nylander-Roslovic look would give the club a chance to chase more offense without sacrificing too much balance. [Read more 🡒]