The Toronto Maple Leafs could have a major issue brewing right beneath their feet. Several superstar players are up for contract extensions this season. And, the tug of war between teams and agents isn’t letting down.
The most notable examples are Connor McDavid and Kirill Kaprizov. They’re seemingly keeping their respective clubs hostage with their rumored contract demands. McDavid and Kaprizov are the proverbial canary in the coal mine.
Depending on what terms they get from their respective clubs, other major stars like Jack Eichel, Artemi Panarin, and Martin Necas, to a lesser extent, could reap the benefits of potentially record-setting deals.
With the perspective in mind, is it too soon to worry about Auston Matthews’s next contract? The Maple Leafs’ captain is entering the second year of a four-year extension signed last summer.
Now, there doesn’t seem to be any sort of warning light on the dashboard signaling that Matthews could bolt. There hasn’t been any sort of dilemma with Matthews as there was with Mitch Marner.
In hindsight, it now makes sense why Matthews opted for a four-year deal instead of a max-term eight-year pact. His agent knew the cap would rise substantially by 2027. So, that timeline fits perfectly with Matthews’s impending free agency in 2028.
The cap will spike to $113.5 million ahead of the 2027-28 season. Right when Matthews would be eligible to sign an extension. Matthews will be 30 by then, and potentially looking at one final max-term deal. Per the new Collective Bargaining Agreement (CBA), that would be a seven-year deal if he re-signs in Toronto.
With that in mind, the Maple Leafs must be thinking several moves ahead. The club has to be wondering how much it will take to keep Matthews in Toronto.
Matthews’s next contract with Maple Leafs depends on his playoff success

Auston Matthews’s next contract with the Toronto Maple Leafs will largely depend on his playoff success. Sure, if he breaks 70 goals, that could be something highly valuable. Another Hart Trophy, Art Ross, scoring title, 100-point seasons, all of that is fantastic.
It’s what Maple Leafs fans want from their captain.
But at the end of the day, it will be the club’s playoff success that will determine how much Auston Matthews gets paid on his next contract. Assuming the Leafs finally get over the hump and bring a Stanley Cup to Toronto, Matthews could get more money than Kaprizov and McDavid.
Multiple Cups from now till 2028 would easily make Matthews the highest-paid player in league history.
But the opposite could also happen. The Leafs could flame out year after year until 2028. Such a situation would tank Matthews’ value, not just in Toronto, but also for other clubs.
Unless a team believes that Auston Matthews is worth $18 million AAV despite not having won a championship, he’s not going to get his payday.
Yes, Matthews took a massive gamble on himself and the Leafs by signing a short-term deal. It’s partly the reason why Marner cashed out when he did. Instead of betting on himself, he set himself up for life now.
Matthews didn’t do that. He made a major bet on his ability and the Leafs’ fortunes in the next three seasons. For the sake of every member of Leafs Nations, the gamble has to pay off.