Kyle Dubas could be preparing to extend Ryan O'Reilly

The Leafs traded a lot of draft capital to complete the deal, sending their own 2023 first round pick, a third round pick (OTT) as well as a 2024 second round pick to St. Louis along with Adam Gaudette and Mikhail Abramov. The Leafs also sent a 2025 4th round pick to Minnesota for helping to broker the deal and make the money work.

Given that this trade goes against everything Kyle Dubas said a couple of weeks ago about giving up a first round pick for a rental, could there be an extension in the works for O'Reilly and/or Acciari already? It's quite possible, and if not, there is a strong possibility there will be extension talks down the line. O'Reilly is a Toronto kid and could follow in the footsteps of Mark Giordano, who signed a 2-year sweetheart extension this past summer.

O'Reilly wouldn't come nearly as cheap as Gio, but could agree to sign for less than the $7.5M cap hit that he's carried since 2016-17. He just turned 32, so he has some quality hockey years left. Would he have any interest in playing out the rest of his career as a Leaf? Could something like 5 years at $4.5M per season make sense for O'Reilly to be able to play at home and pursue multiple Stanley Cups? It's certainly possible. Stranger things have happened.

With Alexander Kerfoot a pending UFA and making $3.5M this year, imagine replacing Kerfoot on the roster with O'Reilly for $4.5M - a slight increase of just $1M per season. Imagine the extra value you'd get out of that additional $1M. It's certainly something worth thinking about.