The Toronto Maple Leafs have a two-year window to go all-in on contention regardless of Gavin McKenna's entry-level contract situation. John Chayka doesn't have his first-round pick in the next two drafts available to him, which leaves no reason to sink back to the bottom of the standings, and Auston Matthews has just two years remaining on his current deal. It has never been more of a win-now mode for the Maple Leafs.
The flexibility of McKenna's contract in the team's top six is a great luxury. Add in Easton Cowan also potentially owning a top-six spot in the lineup over the next two seasons on his entry-level deal, and the Maple Leafs have a level of flexibility that they haven't seen in a long time.
The problem that remains for Toronto is that some of their other contracts are anchors. If Chayka decides to keep Morgan Reilly in the organization, and no other moves to get rid of salary are done, the flexibility that McKenna and Cowan offer doesn't mean a whole lot. They have zero players on expiring contracts heading into the 2027 offseason, which means that in these next two years the salary cap savings will only come from the cap rising if they don't trade any big salary players.
Darren Raddysh, Sergei Bobrovsky, Colton Sissons, Jack Roslovic, and Nick Paul make up $27 million in annual value towards the salary cap. With a lack of UFA talent on the board this offseason, it was really close to the best that Chayka could have done, but it is a bit concerning that McKenna and Cowan's entry-level window is being tied to these players.
The Maple Leafs front office has been very active so far.
— Leafslatest (@Leafslatest) July 2, 2026
How do you rate the Leafs’ offseason so far, based on the players and coach OUT vs. the players and coaches IN? 🤔#LeafsForever pic.twitter.com/5lUj5VUjs2
The two biggest rumors in trades this offseason have been Matthew Knies and Morgan Reilly, which would open another $15.25 million up for Chayka to improve the team further. The question the new general manager has to ask is whether he can improve the team with that amount of money, or whether the loss of both players would leave a bigger hole than everyone thinks.
Toronto is in danger of staying mediocre and walking McKenna and Cowan right to their next deals. With the value of contracts to young players getting higher and higher, it'd be a dangerous game for Chayka not to maximize this window with two top-six players on entry-level deals.
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