Jeff O’Neill isn’t ready to hand the Maple Leafs a clean bill of health just because their offseason looks busy on paper.
Toronto general manager John Chayka has spent his first summer on the job trying to reshape a team that stumbled through a miserable 2025-26 and missed the NHL playoffs. Plenty of people around the league have liked the look of the moves. O’Neill, though, is urging a little restraint.
The former Maple Leafs winger and longtime Toronto media voice made his case during a recent appearance on TSN’s OverDrive with host Bryan Hayes and guest host Jonas Siegel. Asked which Leaf he’d most want to hear from when the team reports for the new season, O’Neill didn’t hesitate.
“Auston Matthews.”
What he wants to know first is simple: where Matthews stands physically. From there, O’Neill widened the lens and talked about what happens when star players spend year after year in the same place without a Stanley Cup to show for it. Using Connor McDavid as an example, he said those players can get “grumpy” and “impatient,” then eventually “grizzled” as the NHL grind wears them down and they’re “not in a great mood.”
That led him to the core question hanging over Toronto.
“I wonder about these guys that have been around this team (Leafs) for so long.”
O’Neill specifically pointed to Matthews, William Nylander, Morgan Rielly, and John Tavares, wondering whether they’d come into training camp carrying a chip on their shoulder. He answered his own question by saying they probably wouldn’t because “it’s just not really in their personality.” Instead, he suggested the more familiar version of camp might be the one Toronto has seen before: the same positive tone, the same professional answers, the same affection for one another.
Both Hayes and O’Neill agreed it would be a welcome change if some of the Leafs’ key players arrived with a fiercer edge.
Hayes then asked the bigger roster question: “Has there been enough change to make this feel different in terms of projecting next season?” He ran through the list of changes - Chayka, Jim Hiller, Darren Raddysh, Sergei Bobrovsky, and Gavin McKenna - and wondered whether enough had actually been reset to create a true fresh start with so many familiar faces still tied to the team’s recent past.
O’Neill’s answer was blunt.
“I think it's a complete roll of the dice.”
He said he appreciated that Chayka recognized changes were necessary and that some players needed to move on because the team simply wasn’t good enough. “They had to kind of flush things out, get some different faces on there.”
Still, O’Neill doesn’t believe new names automatically solve old problems. He brought up the Vancouver Canucks as a cautionary example, noting the parallels between Quinn Hughes in Vancouver and Matthews in Toronto. In his telling, the Canucks added players to keep Hughes happy, only to see him traded after he said he wouldn’t re-sign there.
Toronto, O’Neill said, is trying to do something similar around Matthews over the next two years.
“They (Leafs) brought in a bunch of different faces, but it just doesn't automatically work.”
For him, the challenge is how quickly all of the pieces can start fitting together. New players, old players, chemistry, trust - it all has to come together fast.
“It is, honestly, it is a coin flip. Like, it could be outstanding and it could just fall flat.”
He said that’s the risk with a major overhaul done on the fly, especially when so many moving parts are involved and the group doesn’t know each other well yet. And in his view, the opening stretch matters a lot.
O’Neill stressed the importance of the first 20 games and the danger of getting buried early in the standings.
He finished by circling back to the same point: Toronto has plenty of question marks, even after the offseason shakeup. He did say he likes that the Leafs were willing to make changes and bring in different players. But the summer headlines, he warned, don’t guarantee anything once the games start.
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