Jack Roslovic’s Reset: Toronto Might Unlock a Version Oilers Couldn’t

Jack Roslovic had to wait until October 8th, 2025 to sign his last contract. The Edmonton Oilers — who ultimately inked him to a one‑year, $1.5 million AAV deal — were literally in the middle of their home opener against the Calgary Flames when the signing became official. It was announced during the second intermission, just before the Oilers blew a late lead and lost 4–3 in a shootout.

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Roslovic’s Season in Edmonton

Roslovic delivered a productive year in Edmonton. He played 69 games, scoring 21 goals and adding 15 assists for 36 points. He nearly matched his career‑high of 22 goals while playing 12 fewer games than the seasons in which he previously hit that mark.

He fit well as a one‑shot scorer — something the Oilers have been searching for — and he showed flashes of chemistry when placed alongside Connor McDavid or Leon Draisaitl. His defensive game, however, remained inconsistent, and Kris Knoblauch’s strict defensive demands led to Roslovic bouncing up and down the lineup. Still, he made franchise history in November, scoring overtime winners in back‑to‑back games, becoming just the second Oiler ever to do so.

But once again, the playoffs told a different story. Roslovic’s postseason struggles continued, echoing the year prior when he was a regular healthy scratch for the Carolina Hurricanes. He played all six playoff games for Edmonton but managed only a single assist.

Toronto Maple Leafs Bound

This offseason, Roslovic didn’t have to wait long. On July 1st, he signed a two‑year deal with the Toronto Maple Leafs worth $4 million AAV — a significant raise from his Edmonton contract. He arrives in Toronto with familiarity: he knows Auston Matthews well and effectively replaces Matias Maccelli, whom the Leafs let walk to the New York Islanders.

When asked on TSN’s Overdrive 1050 about why he chose the Leafs, Roslovic offered:

“Mixture of everything… they 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 really good style of hockey that’s exciting. And just wanted to be a part of it.”

The Leafs aren’t exactly new, but winning the draft lottery and selecting first overall certainly injects that young, vibrant energy he’s referring to. Toronto is one of the most polarizing markets in hockey, and Roslovic will experience that intensity immediately.

His connection with Matthews is real. The two played together on the U.S. National Under‑18 Team from 2013–2015, and reuniting was clearly a major factor. Roslovic, when asked about playing with Matthews again:

“Excited to get pushing with [Matthews], being able to play, pick up some things.”

Will It Work?

The big question: does Roslovic fit with the Maple Leafs?

I believe he does. The prior chemistry with Matthews matters, and if Jim Hiller leans into that connection, it could click quickly. The concern is how Roslovic adapts to Hiller’s system, especially with early projections placing him on the top line. He never fully secured that role in Edmonton, so how Toronto deploys him will be one of the more intriguing storylines heading into camp.

Roslovic is a legitimately useful player. He can finish, he can transport the puck, and when Edmonton finally gave him power‑play reps, he produced. He should see more consistent PP time in Toronto, which is exactly what he needs — more touches, more involvement, more chances to dictate pace. That’s when Roslovic is at his best.

With familiar faces around him, more opportunity, and a full preseason to settle in, Roslovic has a real chance to hit a level he hasn’t reached before. The question becomes whether he can eclipse that 22‑goal mark and push toward 25. It’s a fair bet — and one the Maple Leafs are banking on.

Next: Boudreau’s Blunt Warning: Maple Leafs’ Overhauled Roster Still Flawed