Connor Bedard’s new deal is the kind of contract the Toronto Maple Leafs ought to study closely.
The Chicago star signed a five-year, $75 million contract this offseason as a restricted free agent, and the structure says plenty about where the NHL is headed. Bedard is coming off the best season of his career, posting 30 goals and 45 assists in 69 games for more than a point per game. Even with the debate around whether he has fully lived up to the hype, he produced at a high level on a team where his linemate, Andre Burakovsky, was traded for a sixth-round pick this offseason.
The bigger point for Toronto is what this deal does to Bedard’s future. It takes him to unrestricted free agency at 25, and if Chicago isn’t contending by year three or four of the contract, there’s a real chance he could be looking elsewhere.
That’s the warning sign for the Maple Leafs, because Auston Matthews is on a similar path. He is a free agent two years from now, and if this season goes badly, he could try to force his way out of Toronto in one form or another without a long-term commitment in place.
The NHL’s rising cap is changing the math for stars. Salaries are climbing every year, and over the next five to 10 years, players making more than $20 million a season is going to become normal.
In the old flat-cap setup, the smartest play was often to lock in long term and secure as much money as possible. Now, the leverage is shifting.
Players want flexibility, too. They want control over where they end up and the ability to avoid a Dylan Larkin-type situation.
Reportedly, Chicago wanted an eight-year commitment from Bedard, but Bedard preferred something shorter. The compromise landed at five years, which bought out only one year of unrestricted free agency.
That kind of deal makes sense for elite players in this market. Why tie yourself down for eight years at $15 million if, four years from now, you might be worth more than $25 million? That is the calculation stars are making now.
Matthews could follow the same playbook when he negotiates next. Two years ago, he signed a four-year, $53 million contract with Toronto.
He is in the prime of his career, and another short-term deal would set him up to cash in again when the time comes. The next two seasons already have a known cap number, and star salaries are expected to rise sharply over that stretch.
After that, the cap is not confirmed, but the expectation is that it will keep climbing.
For Matthews, a short-term contract at a high AAV would mean another major raise on the next deal instead of settling for a longer-term arrangement that pays less on the back end of his career. That is the appeal for young stars right now: more leverage, more money, more control.
Toronto will spend for a player like Matthews. That part is never really in doubt.
The tougher question is whether the Maple Leafs can convince him to stay through the rest of his prime if they have another rough season. Ring chasing has become a real trend over the last two seasons, with players eyeing places like the Minnesota Wild, Vegas Golden Knights, and Florida Panthers.
The Maple Leafs have long been one of hockey’s destination teams, but they still haven’t put together a major postseason run in the last decade. If Matthews leaves as a free agent or pushes his way out in a trade, that becomes an even harder problem to solve.
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If Rielly remains in Toronto, the path forward may look different than it has in past seasons. A lighter load could actually work in his favor, both by giving him more room to contribute offensively and by easing some of the pressure that has followed him, while the coaching staff continues to sort out pairings and power-play usage with several new options in the mix. [Read more 🡒]