The Maple Leafs' Three Toughest Contracts for 2026-27, and What They Cost

The Maple Leafs' toughest contracts start with the one signed five weeks ago

The hardest of the Maple Leafs' toughest contracts to defend is not a legacy deal from a previous regime. It is Colton Sissons at $4.25 million per season, signed on July 1 by the general manager who is supposed to be fixing exactly this problem. Toronto is projected over the $104-million salary cap, is relying on long-term injured reserve to get compliant, and is carrying three contracts that will cost real flexibility over the next two seasons. Two of them are John Chayka's.

This is not a case that Chayka has had a bad summer. The bottom six is deeper, the crease is settled, and the club got younger in places. But cap teams do not fail because of one catastrophic deal. They fail because of three medium ones that each look survivable in isolation.

Colton Sissons: $4.25 million for a fourth-line centre

Sissons signed a two-year, $8.5-million contract on July 1 after arriving from Vegas. The cap hit is $4.25 million. He is a legitimate NHL penalty killer and a defensively responsible centre who wins faceoffs and does not get caved in. He is also, on this roster, a fourth-line centre.

The number is the issue. Toronto already committed to a bottom-six overhaul this summer — Sissons, Teddy Blueger, Jack Roslovic, Nick Paul, Brandon Duhaime — and the group is genuinely better than what it replaced, as we argued in our look at how Chayka's depth rebuild is meant to unleash the core. But paying $4.25 million for the fourth-line centre on a team that is $2.75 million over the cap is the definition of a self-inflicted constraint. That single contract is larger than the club's entire overage.

The term saves it. Two years is short enough that this does not become a millstone, and Sissons's skill set — penalty kill, defensive-zone starts, faceoffs — is the kind that ages more gracefully than scoring. But if Toronto needs to add a top-four defenceman in February, this is the money that would have paid for it.

Dakota Joshua: $3.25 million and a shrinking role

Joshua came over from Vancouver in July 2025 for a 2028 fourth-round pick, carrying a $3.25-million cap hit on the four-year deal he originally signed with the Canucks. Two years remain.

The problem is not the acquisition cost, which was nothing. It is that Joshua has not played to the salary and has been pushed down the lineup as Toronto added forwards around him. A $3.25-million fourth-liner is an awkward asset — expensive enough to matter against the cap, not productive enough to justify a bigger role, and not cheap enough to bury without consequence. We wrote earlier this summer about why he is Toronto's most obvious cap-clearing trade chip, and the offseason since has only strengthened that case.

The wrinkle is that Joshua and Sissons now compete for the same minutes. Toronto has assembled a fourth line good enough that someone useful gets scratched — a genuinely nice problem that also happens to cost $7.5 million in combined cap hits. That tension is the subject of our piece on the fourth line and who ends up in the press box.

Morgan Rielly: $7.5 million, four years, and a no-move clause

Rielly is the largest of the three and the least moveable. He signed an eight-year, $60-million extension in 2022 that carries a $7.5-million cap hit and runs through the end of 2029-30, when he will be 36. It includes a full no-move clause, with a modified 10-team no-trade attached to the final two seasons.

Rielly has been a genuinely important Maple Leaf for more than a decade and there is no version of this where the contract was unreasonable when signed. The difficulty is structural: a defenceman on the wrong side of 30, with declining foot speed, at $7.5 million, on a team whose most obvious roster hole is a top-four defenceman. The clause means Toronto cannot solve it unilaterally even if it wanted to.

Chayka has said he does not anticipate trading Rielly. Plenty of people who cover the league did not take that at face value, which we unpacked in our piece on the gap between what Chayka said and what insiders believe. The honest read: this is a contract Toronto lives with, not one it escapes.

The counterweight: what Toronto got right

A fair accounting has to include the other column. Gavin McKenna's entry-level deal — a $3.225-million maximum base with Schedule A and B bonuses over three years — is the most valuable contract on the roster relative to production, assuming he plays the way the No. 1 pick is supposed to. John Tavares at his current number is a bargain second-line centre. Jack Roslovic at $4 million after a 21-goal season is priced like depth and could play higher.

That is the point of the exercise. Toronto is not a team drowning in bad money the way it has been in past summers. It is a team with three contracts that each eat between $3 million and $7.5 million and return less than that in value, on a roster where the difference between a playoff team and a lottery team is probably two or three wins.

Why this matters at $104 million

The cap went up. The salary cap for 2026-27 sits at $104 million, a meaningful jump, and it is why Toronto could afford a summer of additions at all. But the cap rising does not help a team that spends the increase before the season starts.

Toronto's projected cap hit is roughly $106.75 million on 23 players, about $2.75 million over. The club gets compliant the usual way — Max Domi opening on LTIR, a depth forward or two starting with the Marlies — but LTIR compliance means no accrual and no in-season room. A team operating that way cannot add at the deadline without subtracting first.

Add the three contracts above and you get roughly $15 million committed to a fourth-line centre, a fourth-line winger and a 32-year-old defenceman. That is the entire margin between Toronto's current roster and one that could absorb a real addition in February.

The fix, such as it is

There isn't a clean one. Rielly's no-move rules out the biggest number. Sissons was signed five weeks ago and has negative trade value at $4.25 million until he plays well enough to change that. Joshua is the realistic candidate — two years, $3.25 million, a role the Leafs have made redundant, and a price low enough that a cap-floor team could take him without retention.

That is one move worth about $3.25 million. It is not nothing, and it would get Toronto to compliance without LTIR gymnastics. It also would not solve the top-four defence hole, which remains the actual problem with this roster and the reason the models still have the Leafs as a bubble team.

What's next

Nothing has to happen until camp. The offseason cap allows a 10 per cent overage, and Chayka can wait for other clubs' rosters to settle — particularly for the league's unsigned restricted free agents to sign, which is what unfreezes cap space across the NHL.

The tell will be whether Toronto moves a contract before the exhibition schedule begins. If the answer is no, this group starts the season in LTIR relief with no deadline flexibility, and the three contracts above become the reason. Track the full cap picture on our contracts page and the roster on the players page.