Matthews positions himself to be greatest Maple Leaf of all time with savvy extension

Nick Kypreos joins Ken Reid to discuss why Auston Matthews was looking to sign a shorter-term deal to stay with the Toronto Maple Leafs and also why he believes William Nylander won't re-sign before the start of the season.

TORONTO — The hope, the dream here is that Auston Matthews lifts the Stanley Cup in a Toronto Maple Leafs sweater, drafts a rewrite of the franchise record book, and is one day bronzed on Legends Row. The idea being that, with team success, the one-time Hart Trophy winner, two-time Rocket Richard champ has positioned himself with a good shot to go down as the greatest Toronto Maple Leaf of all time.

But what Matthews assured Wednesday — roughly a month prior to the circus of training camp’s opening media frenzy — was that he will surely go down as one of the savviest business minds in hockey’s long line of millionaire superstars.

By inking a four-year, $53-million contract extension to remain with the club that tanked to draft him in 2016 — hey, you gotta be bad to be lucky — Matthews guaranteed himself $113.97 million in total NHL earnings by the time he gets set to become an unrestricted free agent in 2028. At age 30. When the salary cap is projected to be enjoying a joyous spike.

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Maybe then he’ll opt for the maximum term, which, to our knowledge, was never a serious option on this round of negotiations with newly hired general manager Brad Treliving.

By all accounts, talks to make Matthews the highest-paid player by 2024-25 —he’ll eclipse Nathan MacKinnon’s $12.6 million AAV, which edged out Connor McDavid’s $12.5 million — were amicable throughout and centred around three-, four- or five-year options.

For the No. 1 centre — who broke his own extension news on Twitter, allowing nervous Leafs fans a sigh of late-summer relief — he gets a handsome payday, avoids ins-season distraction, and (health permitting) sets himself up lovely for another big swing at the open market in his late prime.

McDavid will surely re-raise the high bar as a free agent in 2026 (heck, Leon Draisaitl might do it in 2025), so Matthews will be negotiating in a whole new landscape come ’28.

For Treliving and the Maple Leafs, they lock up the best years of a superstar career and signal to the sport’s most tortured fan base that they’ve got at least five more years of going for it.

Of touching, as Matthews tweets, “the top of the mountain.”

On Tuesday, we could not guarantee Toronto’s contention window beyond 2024. By Wednesday evening, that window had expanded through ’28.

That’s how much true No. 1, game-breaking pivots matter.

Sure, plenty of questions will surround Matthews’ supporting cast. 

William Nylander — who wants to stay and is in no hurry to sign — leads a long list of impending UFAs on a roster that includes a No. 1 goalie (Ilya Samsonov), a top pure defender (T.J. Brodie), and a trio of one-year rentals (Tyler Bertuzzi, Max Domi, John Klingberg) who may or may not stick around for the long haul.

What Matthews’ relatively quick and reasonable re-signing does, though, is assure all current and future Leafs that this team means business.

And so does Matthews.

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