NASHVILLE — Let’s start with Auston Matthews. 

First, if you still had any doubt, even after the public declarations: Matthews wants to stay in Toronto. He wants to win in Toronto. He wants to be a Maple Leaf.

That’s a significant positive for the team.

The complication is Matthews is not willing to go along with the status quo for players of his ilk – think Nathan MacKinnon – when it comes to his next contract. We’re told he wants to be compensated as one of the best players in the league, a 25-year-old with a Hart Trophy, two Rocket Richard trophies, and multiple All-Star Game appearances.

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The rapidly rising cap environment is the key part of that complication.

The salary cap might be the most important thing to remember about where this is going. The belief is that Matthews and his agent, Judd Moldaver, want his third NHL contract to account for a cap that should hit $87.5 million in the fall of 2024, when the new deal kicks in, and is expected to only go up from there, as much as five percent annually.

Which means a cap hit figure that will shrink over the life of the contract. 

That is why it’s likely they will be looking at a contract ranging between two and five years long. The sweet spot, for both Matthews and the Leafs, may be a five-year deal with a record-setting cap hit, higher than MacKinnon’s $12.6 million annual average value.

A five-year deal would buy up the entirety of Matthews’ prime, his age-27, 28, 29, 30, and 31 seasons. It could also shatter the previous precedent for these types of contracts. The Leafs could be looking at a number as high as $14.5 million on the cap on a five-year deal.

Which obviously seems high.

But consider the way the cap hit percentage may shrink over the life of the deal as the cap rises:

A five-year at $14.5 million per season

That cap hit percentage of 16.6 percent in year one would just about match the 16.7 percent that McDavid scored in year one of his current eight-year deal. (McDavid will get about 15 percent of the cap next season.) But it eventually falls to under 14 percent by that final season.

For comparison’s sake, John Tavares’ $11 million cap hit was worth 13.8 percent of the cap when the Leafs signed him to a seven-year contract in 2018. Even at his absolute best, he’s never come close to Matthews as a performer for the Leafs. 

The belief is also that Matthews might consider a seven or even eight-year deal, but only if the deal came with a cap hit that accounted for where the cap is going, not where it is today. 

An eight-year deal, for instance, might come with a $16 million cap hit, given how high the cap is projected to rise.

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Which, again, seems like a lot.

But by the end of the deal, the cap might be well over $120 million, making for a cap hit percentage of about 13 percent in the final season.

Now obviously a $16 million cap hit in next year’s cap climate would make things difficult for Toronto, which is why bringing the term down for a lower cap hit makes sense for both sides. A lower cap hit will help the Leafs fill out the team around Matthews. 

It’s worth noting, too, that Tavares’ $11 million cap hit will disappear from the Leafs’ books after one year of Matthews’ next deal.

The Leafs haven’t gotten too far along in contract talks just yet. And don’t be surprised if nothing is done on July 1. Matthews’ new deal should get done before the start of next season though and may begin to alter the landscape and shift the thinking for top players in the sport. 

GO DEEPER

Why Auston Matthews should take a short-term deal and change the NHL contract landscape

It’s really only in hockey that the stars, the biggest stars especially, are expected to take less. It’s part of a team-first mentality that’s hardened in the sport, especially in the salary cap era. Stars take less because they’re supposed to take less to help the team.

Matthews pushed back against that with his last deal (five years, $11.634 million cap hit) and appears ready to do so again this time around.

It’s a step toward revolutionizing the pay structure in the NHL so stars get their full worth.

But being first makes push-back inevitable, understandable even. All the more so when other stars are willing to take less in service of their teams.

Matthews may not owe it to the Leafs to take less or agree to the full term like those peers of his did. But it’s entirely reasonable to argue that the Leafs might have a better chance of ending their long Stanley Cup drought were he to follow along with his peers. 

It’s also entirely possible the Leafs take the savings they get from Matthews (if he accepts less) and spend it poorly. 

GM Brad Treliving will have to decide what the best achievable outcome is with Matthews. He and the Leafs may want the full eight years but may not be prepared to pay up to get it. A five-year deal gets them some term and a cap number that they can work with.

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As of now, the only Leafs under contract for the 2024-25 season – when Matthews’ new deal will begin – are Tavares (last year of his deal), Mitch Marner (last year), Morgan Rielly, Calle Järnkrok, David Kämpf, Matthew Knies, Pontus Holmberg, Jake McCabe (last year), Joseph Woll (last year), and Conor Timmins (last year).

William Nylander might soon join that list. Or not. 

Nylander’s agent, Lewis Gross, met with Treliving during draft week in Nashville. It wasn’t the only time they’ve spoken about Nylander’s next deal.

This one is even thornier than Matthews.

That’s because a) Nylander has a 10-team no-trade clause that kicks in on July 1, which puts a soft deadline on negotiations for the Leafs and b) seems to be seeking more money than the Leafs are willing to pay.

Nylander wants to be a Leaf. He’s told Treliving and team president Brendan Shanahan as much. He also wants to be fairly compensated, especially compared to his fellow Leaf stars who he’s, arguably, outperformed in the playoffs.

If the Leafs do want to keep Nylander, they need to find a way to make it all work under the salary cap.

But what’s the Leafs’ walkaway number for Nylander? What if Nylander seeks a cap hit in the double digits that pulls him closer to Matthews, Marner, and Tavares? If the Leafs aren’t willing to go there, or even in the range of $9-plus million, will they pivot before that no-trade clause kicks in?

In other words, will they trade Nylander on Friday? Is that even possible if you’re doing it right? Or will the Leafs grind on beyond July 1 and risk limiting the pool of suitors if they can’t come to a deal?

Might they consider letting Nylander play out the last year of his current deal, which carries a cap hit ($6.96 million) that currently ranks as the 96th highest in the NHL for next season?

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Part of the problem for the Leafs is that Nylander’s camp doesn’t appear to see July 1 as a deadline.

Next July 1, when Nylander’s current deal runs out, is their deadline. 

(Top photo: Gavin Napier / Icon Sportswire via Getty Images)