John Chayka has already turned the Toronto Maple Leafs over at a dizzying pace, and yet the biggest question hanging over the team is whether he still has one more major swing left.
Four months into the job, Chayka has remade the roster in a hurry. Since arriving in May, he has moved Joseph Woll, Simon Benoit, Brandon Carlo, Nick Robertson, and Dennis Hildeby, while also letting Matias Maccelli and Calle Jarnkrok leave in free agency. On the way in, Toronto added Sergei Bobrovsky, Darren Raddysh, Colton Scissions, Emil Andrae, Jack Roslovic, Nick Paul, Brandon Duhaime, and even drafted Gavin McKenna.
That kind of turnover naturally fuels the idea that another blockbuster is still coming. Around the league, Morgan Rielly, Dakota Joshua, and Oliver Ekman-Larsson have all been mentioned as names still in play, with Rielly the biggest of them.
Even with Chayka hinting the defenseman is staying, the chatter has not gone away. People around the league describe Chayka as someone who “loves making deals,” and the expectation in some circles is that another significant move could still land before training camp opens in September.
There have also been other names tied to Toronto. The Maple Leafs were linked to Zach Werenski when he briefly became available out of Columbus, and some have wondered about Dylan Larkin, even though Toronto is not on his preferred list.
But there is a strong argument that the big splash has already happened. The Woll trade with Philadelphia was a major one.
The Raddysh move was a serious swing. Drafting McKenna could reshape the future, and signing Bobrovsky was the kind of gamble that can define an offseason either way.
The market also appears to be narrowing. Chayka has made it clear Rielly is not being moved, and trade talk around him has cooled. With the Werenski noise out of Columbus having fizzled and the player pivoting back to wanting to stay with the Blue Jackets, the obvious blockbuster target no longer seems to be there.
There’s also the matter of timing. Toronto does not need to force another massive move right now when there’s always the chance to strike in-season instead.
If Chayka wants flexibility, that matters. One more giant trade would close off the possibility of pouncing later on a player who becomes available then but is not available now.
So if this is a verdict, it tilts toward ending. Chayka will keep looking, and the Maple Leafs will keep their eyes open, but at the moment there does not seem to be a blockbuster on the verge of happening.
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Easton Cowan has already built a rare postseason rsum before even settling into the NHL conversation in Toronto. He won the Memorial Cup with the London Knights in 2025, then added the Calder Cup with the Toronto Marlies in 2026, giving Leafs fans a glimpse of a prospect who has been around winning from the start.
Now there is a chance for something even stranger, and maybe unprecedented, if the Maple Leafs can finish the job in 2027. A Stanley Cup would give Cowan three straight championships in three different seasons, a run that is notable enough on its own and unusual enough that it is not even clear whether anyone has pulled it off before. [Read more 🡒]
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Maple Leafs Suddenly Look Like A Team Fans Should Fear Again
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It is the kind of broad roster makeover that can change the feel of a team quickly, especially for a club coming off a year that fell short of expectations. On paper, the mix gives Toronto more options up front, more stability on the back end and a new look in goal, which is enough to make the Leafs appear far more dangerous than they did a season ago, even if the real answer still has to wait for the games to start. [Read more 🡒]
