Jack Roslovic Is the Maple Leafs' Riskiest Bet of the Summer

Jack Roslovic and the Maple Leafs made a deal that only works one way

Of everything John Chayka did in July, the Jack Roslovic signing is the one most likely to look bad in April. Two years, $8 million, a $4 million cap hit for a 29-year-old winger who has been in the league a decade and has never held a top-six job for a full season on a good team. Toronto is paying him like a solution. The evidence says he is a streak.

This is not a case against Roslovic the player. He is a legitimate NHLer with real speed and a real shot, and there are nights when he is the best forward on the ice. It is a case against the price and the role, on a roster that has almost no margin for a $4 million miss.

Toronto is roughly $2.75 million over the $104 million cap before anyone plays a game. In that environment, $4 million is not a depth signing. It is a bet.

What Toronto actually bought

Roslovic put up 21 goals and 15 assists for 36 points in 69 games with Edmonton last season, on a $1.5 million contract he signed in early October after the market passed him over. By raw production that is a good year and a bargain. It earned him the security and the raise he had been chasing since the previous summer, when Toronto was reportedly interested but could not fit him under the cap.

Look closer and the season splits into pieces. Roslovic caught fire in November — nine goals and 14 points in the month — which was also the month he spent the most time playing beside Leon Draisaitl. He was promoted to Edmonton's second line, then to the first. Production followed the linemates, as it usually does.

Then the playoffs. One assist in six games, and a nine-game goalless drought spanning the last three games of the regular season and every game of the postseason. Edmonton's own beat coverage described him as extremely streaky, capable of going invisible for multiple games at a stretch.

That is the player. Hot for three weeks, gone for three weeks, dependent on who he is playing with.

The career pattern is a decade long

Roslovic was Winnipeg's first-round pick in 2015, 25th overall. He entered last season with 526 NHL games across four organizations: the Jets, Columbus, a 19-game cameo with the Rangers, and Carolina. Four organizations in ten years is not the résumé of a player teams fight to keep.

The Carolina season is the useful comparison. In 2024-25 he scored 22 goals in 81 games — matching his career high, third among Hurricanes forwards — playing in one of the most structured systems in the league. He was good. Carolina let him walk anyway, and he sat unsigned into October.

Two teams that watched Roslovic produce at close range declined to keep him at anything near $4 million. That is not proof he is overpaid, but it is information, and it is the kind of information a rebuilding front office is supposed to weigh more heavily than the goal total.

Why the fit is awkward

Here is the structural problem. Roslovic's best NHL work has come as a complementary piece next to an elite driver — Draisaitl in Edmonton, Sebastian Aho's supporting cast in Carolina. Toronto has exactly two of those drivers: Auston Matthews and William Nylander.

So either Roslovic plays with one of them, in which case he is occupying a slot that Matthew Knies, Easton Cowan or Gavin McKenna could fill for a fraction of the money, or he plays on the third line, in which case Toronto is paying $4 million for a complementary winger who is no longer complementing anybody.

That is the whole tension of the signing, and it lands directly on the open top-six competition at training camp. Three players, two jobs, and one of them has a contract that argues for him whether or not he earns it.

The blocking problem

This is what worries me most, and it has nothing to do with Roslovic's ability.

Short camps favour veterans. The preseason is eight days long this year, Toronto plays a handful of exhibition games, and Jim Hiller has to install a system while sorting a lineup. In that environment, a coach reaches for the known quantity. Roslovic is the known quantity. He is also 29, on a two-year deal, on a team whose entire future runs through an 18-year-old and a 21-year-old.

If Roslovic opens on Matthews' wing and McKenna opens on the third line, that is a defensible October decision. If it is still true in January because nobody wants to bench a $4 million veteran, Toronto has wasted a developmental year on the most important player it has drafted since 2016. We laid out the case for McKenna's rookie ceiling this week, and it is entirely contingent on him getting minutes with people who can pass.

The same applies to Cowan, who went from healthy scratch to 20-minute nights over the course of last season and has earned an actual runway. We argued Chayka should not trade him. That argument only means something if he plays.

The case for the signing

To be fair to Chayka, there is one.

Toronto scored badly last season and finished last in the Atlantic at 32-36-14. A team that bad up front does not have the luxury of leaving 20-goal seasons on the free-agent market on the theory that a teenager might replicate them. Roslovic has scored 20 or more in two of the last three years. Whatever the process, the output has been real.

Two years is also short. This contract expires in the summer of 2028, before the McKenna and Cowan extensions become expensive, and $4 million against a rising cap in year two is not a franchise-altering commitment. It is a bridge — precisely the sort of move we described when we looked at Chayka's veteran bridge strategy for this roster.

And the Matthews connection is not nothing. The two are reported to be close, and chemistry between a centre and a winger who already trust each other is a real, if unglamorous, competitive edge. If Roslovic is the guy who finally sticks on Matthews' right side after a decade of auditions, the money stops mattering immediately.

What I would actually do

Play him with Tavares.

Roslovic's skill set — speed through the neutral zone, a shot he does not hesitate to use, an ability to find soft ice — is a better complement to a 36-year-old centre who has lost a step than it is to Matthews, who already generates his own offence. It gives Toronto a genuinely dangerous second line, it keeps a $4 million forward in a scoring role where his contract is defensible, and critically, it leaves Matthews' wing open for whichever of McKenna or Cowan wins it in camp.

That is the version where every dollar on this roster is doing something useful. The version where Roslovic gets handed 1RW in September because he is the safest answer during a short camp is the version Leafs fans will be arguing about at Christmas.

What's next

Camp opens Sept. 16 and Toronto's first preseason game is Sept. 21. Watch the line rushes in the first two days — coaches show their hand early, and Hiller will have decided the shape of his top six before anyone plays an exhibition game.

Roslovic will be fine as a hockey player. He will score 18 to 22 goals, he will have a great November, he will disappear for a stretch in February, and the underlying numbers will be somewhere between acceptable and good. That is who he has been for ten years and there is no reason to expect different.

The question is whether $4 million and a top-six job is the right price for that, on a team that finished eighth in its division and needs its young players to take over. I do not think it is. Check the contracts page and judge for yourself.