Auston Matthews extension means Maple Leafs must be aggressive, creative in pursuit of elusive Stanley Cup

Anyone hoping for drama in the 2024 NHL offseason was sorely disappointed on Wednesday when Auston Matthews announced he had signed a four-year contract extension with the Maple Leafs. Now, the Maple Leafs have five years to win big while one of the best players on the planet is in blue and white.

After landing his massive four-year extension, Matthews is under contract with the Leafs through 2027-28. In that time, Toronto will pay him just north of $64.6 million, and I feel very comfortable saying that Matthews will be worth every cent that hits his bank account.

Matthews, the former No. 1 overall pick, has established himself as a top-five player in the league. Since his rookie season in 2016-17, Matthews has scored 299 goals. No other player has lit the lamp more over that span. His 542 points in 481 games rank 11th in that time, and he still might have another gear in him.

All of this means the Maple Leafs know they have a five-year window to do whatever it takes to snap their 56-year Stanley Cup drought. Players like Matthews don’t exactly grow on trees, and not going all-in with a generational player on the roster would make the Maple Leafs the NHL’s Los Angeles Angels.

In trying to make the most of the next five years, Toronto general manager Brad Treliving will have the chance to be as aggressive and creative as he wants, given some of the decisions he will have to make between now and 2025.

The Maple Leafs will probably take one more big swing at the Cup with its current roster makeup in 2023-24. Under contract along with Matthews are John Tavares, Mitchell Marner and William Nylander. Beyond that, there are some big questions, regardless of whether Toronto breaks through next season.

As things stand, the Maple Leafs have a shade over $54 million committed to 12 players for the 2024-25 season, according to CapFriendly. Assuming the salary cap does jump up to $87.5 million next summer, that would leave Toronto with around $33 million to fill out the rest of the roster.

If Treliving intends to keep Nylander around past this season, there is a good chance that nearly a third of that money will go toward signing the 40-goal scorer to a long-term extension. That said, Nylander isn’t the only notable player set to hit unrestricted free agency in 2024. The complete list is pretty staggering.

That group doesn’t even include defenseman Timothy Liljegren and forward Nic Robertson, who are slated to be restricted free agents at the end of the upcoming season.

The Maple Leafs’ next five years, outside of Matthews, seem a little bit murky as we forecast what the roster might look like in 2024-25 and beyond. That isn’t necessarily a bad thing, though. As talented as the current core is, it has produced 21 playoff wins in the last seven seasons. That won’t cut it in Toronto, and Treliving needs to do everything in his power to change that while Matthews is still one of the best hockey players on this spherical rock.

The Maple Leafs need to explore every option at their disposal, including moving on from at least one of the “Core Four.” That is especially true if Nylander, who is due for a substantial raise after his 40-goal season in 2022-23, does re-sign with the franchise.

At that point, captain John Tavares could potentially become a trade candidate. Following the 2023-24 campaign, Tavares will be 33 with one year left on his contract at $11 million. It might make sense for Treliving to deal Tavares to another team in order to free up money and add draft capital to make another splashy move.

With the salary cap set to go up by roughly $5 million next season, perhaps Treliving could afford to keep Nylander and Tavares in the fold. Tavares clearly has plenty of game left, but could Treliving still build an adequate supporting cast around his stars?

What about Marner, a two-way superstar in his own right? Marner has two years left at $10.9 million on his current contract, which also expires following the 2024-25 season. Signing Marner to an extension will eliminate a large chunk of cap space if he gets anything close to his market value. Would that make Treliving more apt to move him if the right offer comes along next offseason?

It is also important to remember that Treliving might have to completely remodel the blue line after the upcoming season. Morgan Rielly, Jake McCabe and Conor Timmins are the only three defensemen under contract beyond 2023-24, and the latter two will have just one year left on their respective deals.

Treliving will need to make a priority out of finding a top-pairing defenseman to go along with Rielly, and that won’t be cheap, whether in free agency or on the trade market.

Looking ahead to next year’s NHL free agent class, which was dulled a bit by Matthews’ extension, there is at least one tantalizing option for Treliving and the Maple Leafs. Steven Stamkos, who grew up just outside Toronto, is currently slated to hit free agency. Would he be willing to take a hometown-ish discount to help the Leafs capture an elusive Stanley Cup if the team falls short again in the 2024 playoffs?

The Lightning will make a big push to keep Stamkos in Tampa for his entire career, but if the two sides can’t get a deal done, the rumor mill might catch fire in Toronto. Keep in mind that Treliving isn’t afraid to swing for the fences. He was the Calgary Flames’ general manager when, around this time last year, he traded Matthew Tkachuk to the Florida Panthers in exchange for Jonathan Huberdeau and MacKenzie Weegar.

Despite some questions surrounding other players, Matthews is a certainty. There will be no “will he, won’t he” throughout the 2023-24 season, much to the chagrin of those who love a good soap opera. Matthews is locked in for the next five years. Now it’s time for Treliving to use every cent, modicum of draft capital and salary cap loophole at his disposal to deliver a Stanley Cup to Toronto.