John Chayka and Mats Sundin were brought on board to reroute the Toronto Maple Leafs into a better direction, and it’s going to take significant roster changes to make that happen. The offseason retool is coming, Chayka has confirmed in his early days on the job that he won’t be afraid to make bold moves, and Sundin could have some awkward conversations coming with some of the organization’s longest tenured players.

Gavin McKenna or not, the top pick is someone the Maple Leafs are going to welcome with open arms, but that doesn’t change the fact there’s still multiple holes throughout Toronto’s lineup that need to be addressed, and some bold offseason trades will certainly help reallocate some resources moving forward.

Here’s five Maple Leafs who are prime offseason trade candidates now that the Chayka/Sundin era has begun:

This is finally the summer, right? Rielly’s the longest tenured Maple Leaf on the current roster, he’s been here through a ton of ups and downs, and right now, his game is as far ‘down’ as it’s ever been. Rielly’s contract is retool nightmare fuel, as he’s signed for $7.5 million AAV through 2030, and owns a full no-movement clause until July of 2029.

That’s way too long to keep Rielly and his declining game in the mix. He’s lost a step, and it’s impacting his defensive zone coverage a ton when it comes to quick short bursts or ensuring he’s in the proper positioning throughout a cycle. Rielly’s also declined tremendously when it comes to creating offense, moving the puck out of the d-zone and starting breakouts.

Chayka and/or Sundin need to approach Rielly for a list of teams he’d accept a trade to. While many believe western Canadian teams could appeal to Rielly and his young family, one team to keep an eye on would be the San Jose Sharks. They have only two NHL defenseman signed for next season, they have to spend this summer just to get to the salary floor, and they have the most promising up-and-coming roster in the league.

Would a 2026 second-round pick straight up for Rielly, and his entire remaining contract be a deal we see at the NHL Draft? It feels like if the Leafs move Rielly, they should get an NHL-proven third-line center option for him, as moving Rielly for ‘future considerations’ is not going to sit well with Auston Matthews, William Nylander, and company.

Matthews and Nylander both asked for two puck-moving defencemen during their exit meetings, and with Jake McCabe, Chris Tanev, and Oliver Ekman-Larsson locks to come back next season, Benoit will certainly find himself in trade talks.

The 27-year-old rugged blueliner has just one season left on his deal at $1.3 million AAV, and Benoit doesn’t own any trade protection. He dressed in 73 games this past season, chipped in with six assists, landed a whopping 194 hits, while blocking 114 shots, but with the focus on adding skill and mobility to the Leafs’ back end this summer, Benoit’s primed for a change of scenery.

Put it this way, it’s very likely only one of Benoit, Rielly, or Brandon Carlo will be returning next season. Chayka’s made it clear the defensive depth is something he has top of mind, and with a steady push from Nylander and Matthews during their intro meetings, the month of June could be a big month on the trade market for the Leafs’ new GM.

With Gavin McKenna likely en route to Toronto, Nick Robertson could finally get his wish and have his trade request granted this offseason. Robertson’s been through the ringer with the Leafs since being a second-round pick in 2019, and after another inconsistent season when it came to his playing time and usage, don’t be surprised to see some kind of divorce coming in the very near future.

Robertson is a pending restricted free agent, so there’s many different routes this separation could go, but it would just be wise for Chayka to try and cash in on moving Robertson for either a young defenceman with some untapped potential, or a third-line center, who can help create an identity for the Maple Leafs’ bottom six.

Robertson appeared in 78 games last season, scored 16 goals, and 32 points, and a key development piece was the fact Robertson was more efficient with his energy, more physical overall, and his attention to defensive detail in all three zones took major strides.  Unfortunately for the shifty winger, there’s another shifty winger coming, who is loaded with 10x the potential. The Maple Leafs shouldn’t keep Robertson for a potential third-line role, and should listen to Matthews and Nylander, and find some more bite for the bottom six.

Maccelli is in the same boat as Robertson. It’s very unlikely now that there’s a spot for Maccelli in this Maple Leafs’ lineup next season, considering they’re going to add a top-six forward for under $1 million AAV. Yes, there’s bonuses and all of the fine details, but there’s a much lesser chance now that Maccelli gets a long-term contract offer he’s looking for.

Maccelli’s also a pending RFA, he had a great end to the season, but frankly, his attention to detail in all three zones was worrisome this season. As far as vision goes and making high-risk passes, Maccelli takes the cake. But, as a bottom-six winger now in Toronto, that’s not going to fly at all, and neither in his lack of size and physicality.

McKenna in, Maccelli out, it’s bound to happen and a wild turn of events over the course of the last week. We’ll have to wait and see how it plays out with his qualifying offer, but at this point, it’s much more likely Maccelli is playing for a different organization once training camps open in September.

There’s a few reasons Stolarz should be the goaltender moved this summer and it has everything to do with his injury troubles, being five years older than Joseph Woll, and eight years older than Dennis Hildeby. Yes, his contract is harder to move than the others based on the fact his four-year extension is now just kicking in at $3.7 million AAV, and he does own a 16-team no-trade clause, however, $3.7 million for a 1-B goaltender is still a very good price in today’s market.

Stolarz has been bold in Toronto. He’s stood his ground on and off the ice, he’s called out the team multiple times when he doesn’t like what he’s seeing in front of him, however, with Hildeby’s one-way contract kicking in, and with Woll locked in for two more seasons at just $3.6 million AAV, it feels like Chayka will navigate some trade conversations involving his goaltending depth.

The flip side? Toronto’s defense core and defensive structure was dismal last season, so what if they made significant changes to the blueline, the bottom six, and perhaps even the structure, or coaching strategy, could Stolarz get back to his winning ways?

Leafs Nation, prepare yourselves, there’s some change coming this offseason, and if Chayka’s transaction history is any indication, each move will grab your attention, and have you pondering if things will work out or not. Chayka’s been bold with his deals, they’ve been frequent, and heading into the NHL Draft, and with free agency looming shortly after, expect to see significant change coming, and it starts with facilitating some deals.

Chayka’s not taking the job to make friends around the league, he wants to win a Stanley Cup, and he’s ready to reconstruct the Maple Leafs’ roster to do so.