This offseason is shaping up to be one of the most chaotic in the history of the Toronto Maple Leafs. With the team officially out of the playoffs and the Brad Treliving era now in the rearview mirror, the focus has shifted to what feels like a massive retool.
If the rumours and internal rumblings are even close to true, the front office and the roster could look completely different by the time training camp rolls around in September.
A New Front Office Vision
The first order of business for MLSE President Keith Pelley is fixing the front office structure. After they let Brendan Shanahan go in the summer of 2025, Pelley opted to go without a President of Hockey Operations. However, now, after his press conference, it seems that the organization wants to bring that role back and have it completely separate from the general manager. So, after hiring a search firm to help, expect the Maple Leafs to at least explore a push for a proven executive like Tom Fitzgerald or Mike Gillies to take over as President of Hockey Operations. Once that piece is in place, the team is expected to lean more toward a data-centric approach, with someone like Sunny Mehta being the most obvious choice to step in as GM.
This new management group are more than likely going to move on from head coach Craig Berube after his system has failed to click. While they could make a strong push for the highly-coveted David Carle, there is a real chance they fall short because he seems adamant about staying in the NCAA. This means they could end up going with a more familiar option like Manny Malhotra to run the bench.
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If Malhotra is the successful candidate to take over as the Maple Leafs’ bench boss, he could have a chance to be in the same organization as his son. If the Maple Leafs land a top-five pick in the upcoming NHL Draft and pick fourth or fifth, they could decide to draft his son, Caleb Malhotra. This would be a very cool, full-circle moment for him. As he returns to the team that he was an assistant coach for parts of four seasons.
Maple Leafs’ Offseason Moves
The blue line is where the most drastic changes are going to happen. In a move that would signal the end of an era, the Maple Leafs could look to trade Morgan Rielly. The trade would need to be with a team he is open to that can take on his contract. They could also explore moving Simon Benoit to a team like the Montreal Canadiens, or another contender in exchange for a draft pick. To fill that void, the Maple Leafs could take a big swing by signing hometown kid Darren Raddysh to a seven-year, $49 million contract ($7 million AAV). They could also look at reuniting with Timothy Liljegren, which, paired with Ekman-Larsson, could create a good second offensive pairing.
In goal, the team could decide to stick with Joseph Woll as the future. That could make Anthony Stolarz the odd man out, potentially leading to a deal with a team like the Edmonton Oilers, who are desperately in need of a reliable goalie. It would also open the door for Dennis Hildeby to step into a full-time backup role, which feels like something they have been building toward anyway. Up front, the new regime could prioritize speed and skill. Nicholas Robertson should return on a short-term bridge deal (2-3 years) in the $2-3 million range, while Calle Jarnkrok and Troy Stecher should walk in free agency.
Mattias Maccelli could also be on the move. Although he has been good in the second half of the season, it is not worth paying the increase in pay for a middle-six forward, who didn’t help move the needle. So, the team might decide to flip his RFA rights for draft capital, and if they can get back what they paid for him, which was a third-round pick, it would be a great return. As for Dakota Joshua, he served his purpose, but he is replaceable in the bottom six, at a much cheaper AAV. The Maple Leafs should try and trade him to the Philadelphia Flyers, where he can play under Rick Tocchet, for a fourth-round pick. It may be a bit under market value, but the goal here is to clear cap space and moving Joshua does that.
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With the cap space freed up from trading Joshua, Rielly, Stolarz, and Benoit, the front office can essentially spend as freely as possible to try and get this club back on the right track. If they do this while having clear and honest communication with Auston Matthews and William Nylander, it could very well be the reason why they want to stay for at least one more season. They just need to prove to the top stars that they are willing to push through the retool and get back to the team they were in a short period of time.
So, to help with that, the Maple Leafs need to be aggressive in free agency. After hypothetically, signing Raddysh to $7 million per season. They’ve shown the rest of the free agent class they are willing to spend money. Their forward targets should be Charlie Coyle to provide more reliable depth down the middle and reuniting with Bobby McMann, a player they never should have gotten rid of. Their depth signing would be to target Beck Malenstyn, a pesky bottom-six forward who loves to hit but can also score 20 points per season.
For their last big signing, it comes down to Patrick Kane and Anthony Mantha. In this situation, the preference would be Mantha, since he is younger and is one point behind Alex Tuch for the most points in the free agent forward category (61 points). That said, if Tuch does hit the open market, he should be their first option. However, it seems like the Buffalo Sabres are going to re-sign the hometown kid.
Here’s a preview of what their opening night lineup could look like for the 2026-27 season.
Forwards:
McMann – Matthews – Knies
Mantha – Tavares – Nylander
Robertson – Coyle – Cowan
Malenstyn – Domi – Lorentz
Extras: Groulx, Quillan
Defense:
Raddysh – Carlo
McCabe – Tanev
Ekman-Larsson – Liljegren
Extras: Myers
Goalies:
Woll
Hildeby
Maple Leafs Need to Acquire Draft Picks
Realistically, the goal is simple. Trade players on the team who are not part of the future but can still bring back value on the open market. For example, if they were to deal Rielly, they could get a second- or third-round pick, plus a late-round pick and potentially even a player like Curtis Douglas to be a depth forward or minor leaguer. The catch would be that they would need to retain up to 50% of his contract, which is doable with the cap set to rise again this summer.
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In fact, all the trades they make involving players like Rielly, Stolarz, and others should be for draft picks rather than NHL-caliber players or mid-tier prospects that they don’t see a future for. Their main focus should be to ice the best team possible through free agency while also trying to restock their draft pick cupboards as quickly as possible so they can add prospects and younger talent over the next few drafts.
