The Maple Leafs may have let a real bargain window slip by with Easton Cowan.
That’s the kind of edge contenders chase in a hard-cap league: getting premium production before the price tag catches up. Toronto hasn’t exactly made a habit of living in that sweet spot during the Auston Matthews era, and Cowan looked like a player who might have given the front office another chance to cash in early.
The timing is the catch. A new NHL CBA takes effect on September 15, and one of the biggest changes is the maximum length of contracts.
Right now, teams can give their own players up to eight years and unrestricted free agents up to seven. Under the new rules, those limits drop to seven years for re-signing a current player and six years for UFAs.
That’s why players such as Montreal Canadiens winger Ivan Demidov and Philadelphia Flyers winger Tyson Foerster moved early this summer on eight-year deals. It was their last shot at that extra year of security.
Toronto, though, doesn’t have anyone in the final year of a current contract who could have been extended before the rule change. That includes Cowan, who is heading into the second season of his three-year entry-level deal.
And that’s where the missed opportunity lives.
Cowan already looks like a player who could return serious value at his current cap hit, with the upside to become a top-six winger as soon as next season. The fantasy for the Leafs would have been locking him into something like an eight-year deal at a $6.5-million AAV - the kind of contract that can look like a coup if the player develops, and a headache if he doesn’t.
There’s risk either way. If Cowan tops out as a 40-point winger, that deal could age badly. But if he becomes the kind of player who forechecks relentlessly, chips in 20 goals a year, and keeps Toronto in the fight every night, it could turn into one of those contracts teams brag about for years.
Instead, that door is closed. His deal runs through the end of the 2027-28 season, which means the best Toronto can do now is a seven-year extension down the line.
That might still be a smart bet. But if Cowan keeps climbing and posts something like 60 points on a good team, he’ll almost certainly be thinking about maximizing his value rather than trading that for extra security.
So yes, it’s an opportunity lost. Just not one the Leafs could realistically have forced.
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