Maple Leafs' Three Most Challenging Contracts For 2026-27 NHL Season

The Toronto Maple Leafs have taken on a slew of new contracts this off-season. That comes from their abundance of free-agency acquisitions, trades or even Gavin McKenna’s entry-level contract that he signed on the final day of development camp on July 3.

Some contracts are better than others, and some are easy for the team to handle if a certain player needs to be moved. The constant growth of the salary cap helps with the way organizations handle the bigger contracts, and for the Leafs, it’s tough to say there is a very horrible contract that’s holding the franchise back.

Nonetheless, that doesn’t mean there aren’t challenging contracts on the team’s payroll. Whether that be how long the deal is, the salary cap hit, or even the clauses that are included for each player.

Here are the three most challenging contracts on the Maple Leafs’ roster going into the 2026-27 NHL season, in alphabetical order.

Dakota Joshua has two more years left on the four-year contract that he originally signed with the Vancouver Canucks in June 2024. Joshua and his $3.25-million salary cap hit became the Maple Leafs’ responsibility when he was traded to Toronto for a 2028 fourth-round draft pick last off-season.

The main issue with this deal is that Joshua hasn’t played up to the standard of his salary and has been bumped down the Leafs’ lineup as a result. Even with the cap rising, it’s not ideal to have a player earn above $3 million as a fourth liner, unless they provide another dimension to their game that’s rare around the league.

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It’s fair to say that Morgan Rielly hasn’t been playing up to standard over the past couple of seasons. However, he doesn’t perform much lower than how a $7.5-million defenseman should.

After all, he still logs important minutes for Toronto, averaging the second-most minutes on the team for the past two seasons at 21:08 in 2025-26 and 21:23 in 2024-25. And frankly, he’s a top-four defenseman on most teams in the NHL, despite only notching 36 points in 78 games this past year.

Therefore, the issue is not his salary. But if Toronto wanted to move off Rielly to change up the D-corps and for the veteran to receive a change in scenery after 13 seasons with the Leafs, the length of the deal and his clause might be what scares potential trade partners away, or at least from providing a sufficient return.

Rielly has four more years left on his contract, which will take him to the age of 36 when it expires. With that, he has a no-move clause for the rest of his deal, with a modified 10-team no-trade clause attached to the final two years of the agreement, according to PuckPedia.

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Colton Sissons was included in GM John Chayka’s free agency haul on July 1. The former Nashville Predators and Vegas Golden Knights center inked a two-year contract at $4.25 million per season.

For the Maple Leafs, Sissons’ contract isn’t all that back-breaking, just like much of the roster, thanks to the salary cap. However, his cap hit is a little high considering the stature of the player he is.

Sissons has never been a difference-maker offensively, and that attribute is the common denominator in paying a high price tag for a skater, even defensemen. Instead, the 32-year-old is known more for his two-way game and efforts on the penalty kill and faceoff dot. Those are still very much helpful tools to his new team, but it’s not a rare talent.

Still, his cap hit isn’t blasphemy, as he’s still an effective player. But the fact that Sissons’ salary is just about $140,000 less than what John Tavares makes – who is a consistent 30-goal scorer – is slightly puzzling, even if Tavares took an obvious pay cut.

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