Jack Roslovic didn’t need much convincing to see the appeal in Toronto.
The Maple Leafs had just gone through a rough season, but Roslovic still viewed them as a fit worth choosing over other contending options. Familiarity mattered. So did the sense that the group around him could still win.
Roslovic signed a two-year, $8-million deal on the first day of free agency this past summer, and the move brought him back alongside Auston Matthews. It also added a forward with a proven scoring touch after a 20-goal season, giving Toronto another option to support its stars up front.
He also gives the Leafs flexibility. Roslovic can move up and down the lineup depending on what Jim Hiller needs, which fits neatly into John Chayka’s win-now approach built around short-term additions aimed at immediate results.
On TSN OverDrive on Aug. 13, Roslovic laid out why Toronto stood out even after a disappointing year. He pointed to the mix of old and new, and to a style he believes can still compete.
"They've been a team that you could say didn't have their best year last year. But it's a team that is new, it's young, it's vibrant, it's ready to win. A couple familiar faces around, a really good style of hockey that's exciting, and I just wanted to be a part of it."
He also said the influx of new players should help build a stronger bond inside the room, with established names and newcomers blending together.
"With some new faces around, it creates a little bit more in the department of camaraderie. I think we're all super excited about being able to do that, and I think that the core group that's been here for many years is excited about it as well."
"The ability to keep on pushing as fast as we can start pushing the ship with them, it's gonna be really fun."
Roslovic’s confidence lines up with the way Toronto attacked the offseason. Chayka’s roster building has leaned heavily toward the next two years, with most of the summer’s contracts set to expire in 2028. Only Darren Raddysh, Nick Paul, Sergei Bobrovsky, and Brandon Duhaime are signed beyond that point.
That short window makes the goal pretty clear: win soon, while the group is in place to maximize Auston Matthews and still leave room to try to re-sign him when his contract expires.
There may be another layer to that timeline as well. The 2028 window also leaves the Maple Leafs space to re-evaluate the roster around Matthews and Gavin McKenna after the next two seasons.
For Toronto, it’s a calculated gamble after years of playing it safe without fully tearing things down. For Roslovic, it’s a chance to be part of a team built to push now, with his scoring, versatility and familiarity with Matthews all fitting the plan.
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A closer look suggests Toronto may want to slow down on all three judgments. NHL tracking data points to Tavares being less cumbersome than the public narrative says, McKenna could have more room to grow into a role instead of being rushed into the spotlight, and Cowan might be worth a look down the middle if the Leafs want to explore different options. None of that settles the camp questions, but it does make the early roster debates a little more interesting than the usual guesswork. [Read more 🡒]