John Chayka has already put his stamp on the Maple Leafs this offseason. Toronto landed the No. 1 pick in Gavin McKenna, added size and depth up front, and reworked the blue line. Even after that, though, there are still a few obvious places where the roster can be strengthened, and three teams stand out as realistic trade partners once the season gets closer.
That doesn’t mean a deal is around the corner. It just means Chayka looks prepared to strike if the right name surfaces.
One of the clearest fits is in Calgary, where center Morgan Frost keeps popping up in trade chatter. The Flames are deep into a rebuild, and Frost is in the final year of a manageable contract after a career season that produced 22 goals and 43 points. Calgary GM Craig Conroy has made it clear he’s open to moving players who don’t fit the long-term picture, which puts Frost squarely in the conversation.
Daniel Austin of the Calgary Sun wrote:
“Given the opportunity that lies ahead of him, Frost will surely want to put up big numbers this year and earn a bigger deal. It may be worth it for the Flames to give him that opportunity. Their salary cap isn’t an issue going forward, so if he has a great year they’ll be able to reward him.”
source - ‘Five questions for the Calgary Flames in the dog days of summer’ - Daniel Austin - Calgary Sun - 08-11-2026
If Frost blows up this season and starts looking like a player who wants to test the market, Calgary could be better off moving him while his value is high. For Toronto, he would fit a major need. The Maple Leafs are still looking for center depth behind Auston Matthews and John Tavares, and Frost checks a lot of boxes.
Pittsburgh is another situation worth watching. The Penguins have Bryan Rust and Rickard Rakell out there in trade talk already, though the market hasn’t met the price Dubas wanted. Then there’s Erik Karlsson, who is in the final year of his contract and could become a real decision point if Pittsburgh slides out of the playoff picture.
If the Penguins aren’t in position to contend, dealing one of those veterans before they can leave for nothing would make sense. For Toronto, Karlsson is the most intriguing of the bunch, especially after the Leafs were in on Zach Werenski if he didn’t stay in Columbus. Karlsson could become a fallback option.
There are obvious hurdles. His willingness to move matters.
So does the cap. So does the price.
He’s 36, but he still brings real value as a puck-moving defenseman on the right side. He likely wouldn’t replace Darren Raddysh on the power play, which limits some of what he can do, but a pairing with Morgan Rielly would be interesting.
It’s not the kind of name most Leafs fans would automatically circle, and there are reasons to be cautious. Even so, Chayka could test the waters with a lowball offer that includes salary going back, just to see whether Pittsburgh or Karlsson would take it. Rust and Rakell, meanwhile, are already known quantities in terms of what it would take to pry them loose.
Then there’s Werenski, the player Toronto was clearly prepared to pursue. That possibility disappeared when he pivoted back and did a 180 on his decision to leave the Columbus Blue Jackets. For now, the trade that might have been is off the board.
But not necessarily forever. If Columbus struggles and Werenski decides he’s not ready to commit to a franchise that can’t seem to get its ducks in a row, Toronto would be ready to jump back in. He’s the reigning Norris Trophy winner, and only a few defensemen offer that kind of impact.
The Leafs would be willing to pay a steep price if Werenski came available and was open to signing an extension. Matthew Knies would likely be part of the conversation, along with other players the team would normally treat as untouchable. Chayka, it seems, already had an offer in mind before Werenski changed course, and there’s no reason to think that basic framework would change much if the door opens again.
In Other News...
Maple Leafs Blue-Line Plan Changed Over One Price They Wouldn't Pay
Zach Werenski loomed as one of the biggest blue-line swings the Maple Leafs were willing to consider, especially with Toronto reportedly among the clubs he had interest in and the only Canadian team on that list. The Blue Jackets, though, asked for a steep return, with Matthew Knies among the pieces they wanted back, and that quickly pushed the discussion into territory Toronto was not eager to enter.
So the Leafs backed away from the bigger splash and kept their young forward in place, a decision that changed the shape of their defense plans. Instead, Toronto moved in another direction on the back end, settling on Darren Raddysh on a long-term deal and giving the roster a different kind of commitment as the offseason picture took a new turn. [Read more 🡒]
Oilers Face A Big Zach Hyman Successor Debate
The buzz around Matthew Knies has only grown as the Maple Leafs keep searching for ways to shape their future, and his name has now surfaced in a hypothetical deal that would send him to Edmonton as a long-term answer for the role Zach Hyman once filled. It is the kind of proposal that forces both teams to weigh present value against future certainty, with Toronto looking at whether moving a young winger of Knies profile could fit a bigger roster plan.
On the Oilers side, the conversation is about how much they would have to pay to land a player they could build around for years, especially in a market where premium winger trades have not come cheaply. The framework being discussed includes multiple pieces and a protected 2028 first-round pick, which shows the kind of price tag these kinds of swings can carry even before anyone decides whether the fit is worth it. [Read more 🡒]