Toronto Maple Leafs general manager John Chayka is going for it these next two seasons, as win-now mode is alive and well. While he’s already made significant changes to the Leafs’ roster, ahead of training camps opening in September, Chayka likely has another move, or two, up his sleeve.

Joseph Woll and Simon Benoit were traded to Philly. Brandon Carlo was shipped out to St. Louis. Dennis Hildeby was dealt to Tampa Bay. Nick Robertson was sent to Pittsburgh. Chayka loves to wheel and deal, so, who’s next? Here’s three Maple Leafs’ trade candidates to keep an eye on as we move to the back nine of the NHL offseason:

After what felt like an imminent trade ahead of the NHL Draft and free agency opening, Morgan Rielly’s trade talks have fizzled off in a major way. There was a ton of chatter about how Rielly submitted a list of teams, where the four clubs were all in the Western Conference, and it felt like there was a legit shot at Rielly being moved, specifically to the San Jose Sharks.

The Sharks pivoted to Darnell Nurse, and since then, Rielly’s trade market has seemed eerily quiet. Most insiders are saying the same things when it comes to the potential of a deal, that Chayka is open to it, Rielly prefers to stay in Toronto, and if a deal does transpire, don’t expect to see the Leafs retain any of his remaining salary, or add a trade sweetener to the package.

Chayka believes Rielly still has lots of game left in the tank, and isn’t interested in paying a premium to facilitate the move. Rielly’s owed $7.5 million AAV for four more seasons, and his no-movement doesn’t convert to less until July 2028, when he’ll submit a list of 10 teams he can choose to avoid. Does Rielly’s tenure make it to 2028?

The awkward conversation between Chayka and Rielly has taken place, there’s a picture painted of exactly where the veteran defenceman prefers to play, and for now at least, Rielly remains a Leaf. He continues to be linked to the Seattle Kraken and Vancouver as both teams have close to $20 million in cap space, but it certainly feels like a bit of a longshot for either team to take a flyer on Rielly.

Emil Andrae in, Darren Raddysh in, Troy Stecher returning on a two-year deal, and former first-round pick Ben Danford is making serious strides in his development. Add all of this up and the writing is on the wall for Philippe Myers to be given a change of scenery.

The 29-year-old right-handed veteran has been given a ton of opportunity to flourish, and create himself a bigger role with the Maple Leafs, but unfortunately for Myers, he’s fumbled the bag. Myers has dressed in 75 games for the buds in the past two seasons, averaging 14:32 of ice-time last year, and the inconsistent outputs have given Chayka no choice but to ensure there’s plenty of depth at the bottom of his blueline.

At 6-foot-6, Myers seems to always leave you wanting more. The flashes of brilliance and the short spurts of production make it seem like there’s something bigger brewing, but, then a bad turnover or horrible decision with the puck, a lack of physicality or aggression in the dirty areas of the ice, and very quickly, Myers morphs into an AHL defenceman, on the bottom pair of an NHL team.

With more opportunity, and consistent minutes for a longer stretch, perhaps Myers could carve himself out a role somewhere. But for now, with Danford excelling throughout the Calder Cup run for the Toronto Marlies, and showing off a toolbox that appears to be close to NHL ready, and with Andrae being only 24 and full of untapped potential and versatility, and then with Stecher, the savvy vet willing to do whatever it takes to help the team, Myers has quickly become the odd man out. At this point, Myers appears to be the most likely Maple Leaf to be moved before training camp.

Joshua went through the ringer in his first season as a Maple Leaf, and there’s certainly a chance he doesn’t make it to year two. Chayka’s gone out and reshaped his bottom six, created more versatility with the Leafs entire forward group, and a player like Joshua, with a limited skillset and position optionality, he’s quickly become the Leafs most likely forward to get moved this summer.

Joshua appeared in just 55 games last season, scoring 10 goals and chipping in with eight assists. He averaged just 12:14 of ice-time per game, his lowest mark in three years, and rarely saw any ice-time on either side of specialty teams. Chayka’s added Jack Roslovic, Nick Paul, Colton Sissons, Teddy Blueger, and Zack MacEwen, and one thing they all have in common is the fact they’re versatile to  play down the middle or on the wing. Joshua isn’t an effective pivot, so if he wants to hang around as a Leaf, he must shine through with his physicality, and ruggedness to be extremely hard to play against.

It will be interesting to see if Chayka moves off Joshua before the season starts, as the Matthew Knies’ trade rumors have been put to bed, and Joshua feels like the most likely forward to be dealt. At $3.2 million AAV for two more seasons, moving this contract could create some more financial flexibility to add before next season’s trade deadline, because if the Leafs are in the mix of the playoff picture, Chayka’s going for it, there’s no doubt about it. Joshua owns a 12-team no-trade clause, so he’ll have some say in the matter.

For now, trade talks have quieted down, but that doesn’t mean Chayka isn’t involved in conversations to improve his roster heading into his first season as Leafs’ GM. He loves making deals and it’s shown early on into his tenure, so if Toronto’s lead hand sees a move he feels creates better roster construction and flexibility heading into the 2026-27 season, don’t be surprised to see either Rielly, Myers, or Joshua involved.