Right now the Maple Leafs are in a league of their own as they currently have zero expiring contracts on their projected roster as they head into free agency in 2027.
Toronto did a lot of work overhauling their lineup this offseason, adding players such as Darren Raddysh, Nick Paul, Sergei Bobrovsky, Colton Sissons, and Gavin McKenna. It's a much more balanced and defensively sound group that will help relieve some of the tougher minutes the stars needed to play.
A lot of their deals came with the intention of winning now and the multitude of two and three-year deals that were signed give credence to that mentality. Only Raddysh is signed as a long-term player, with everyone else's contract expiring in either 2028 or 2029.
That gives the Maple Leafs a very important advantage as they head into the summer of 2027 - they currently have no projected free agents and everyone is under contract.
While 2028 is a different story with a total of 15 UFA's, the team can relax comfortably for the next two seasons knowing that they have their roster locked up. That means the entire core of Auston Matthews, John Tavares, William Nylander, and Matthew Knies have another two seasons together, and they get more than a year to work with the new pieces.
Cost certainty is a big factor with a rising cap and Toronto knowing what they are paying their players and how much it'll cost them against the projected cap gives them an advantage over other teams because they can plan ahead and budget sooner.
Again, this is based on the projected roster so there is still a possibility a last minute signing or waiver claim on an expiring deal can make the team but as of now - they are the only team with everyone all signed through 27-28.
There is a caveat to this though, as Toronto traded their ability to be flexible in their future for the stability to win now. That means that if this experiment doesn't work out and the Maple Leafs fail to make the postseason or are eliminated early yet again - they're most likely stuck with these deals.
That's $16.5-million put aside to the revamped bottom-six and if they aren't able to fill the roles they were signed to fill, then it's going to be harder to move them and give Toronto some dead money.
The additions also aren't exactly young either. Sissons is 32, Blueger is 32, Bobrovsky is going to be 38 this year, so there isn't a lot of growth potential for Toronto's signings - it's do or die for them right now.
If John Chayka decides to strip things down that means more trades (and potentially more lost assets), waiver claims, buyouts, whichever method necessary because they have to get off those deals somehow.
They can still find deals for those players despite it being harder, and there is still a way for the team to change the roster over internally with some of their AHL players if they were to make trades so they aren't limited when it comes to bodies.
Toronto's commitment to winning now and making sure that Auston Matthews has a better chance in the playoffs gave them two solid seasons with players they can allow to grow and build chemistry together.
But they also may have prevented themselves from moving off if it doesn't work out, and they're betting a lot that these changes make a difference than not - but it's far from guaranteed and they'll have to seriously rethink their plans.
Do you think the Maple Leafs are prepared to change if they don't make the playoffs in 2026-27?
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