If you watched the Toronto Maple Leafs season ending press conference, it’s a safe assumption that change is coming.

And with that change, the Toronto Maple Leafs may look to a familiar foe to trade with.

Prior to leaving the team, Kyle Dubas built this organization into a winner. He loved Auston Matthews, Mitch Marner, William Nylander and John Tavares, and now that he’s a member of the Pittsburgh Penguins, it’s possible that he’d be interested in bringing one of those players south.

The one issue is the no-trade-clause that all four players possess, but by all accounts, they all had good relationships with Dubas and could be interested in joining him in Pittsburgh, especially if it meant playing alongside Sidney Crosby.

Expect Kyle Dubas to Make Big Trade with Toronto Maple Leafs

Eight years ago, the Leafs made an incredible move with the Penguins to send Phil Kessel to the Penguins and it resulted in back-to-back Stanley Cup’s, so Pittsburgh’s organization could hope for the same result this time around.

Sidney Crosby has one year left on his contract, but the expectation is that he’ll sign an extension this summer to stay with the organization. Crosby, alongside Evgeni Malkin and Kris Letang will most likely retire as Penguins, so you shouldn’t expect any of those guys to be in a trade package if Toronto and Pittsburgh made a deal.

However, the one player that Toronto could be very interested in acquiring is goaltender Tristan Jarry. Alex Nedeljkovic is a pending UFA, but if he re-signs in Pittsburgh, Jarry would most likely be on the trade block and the Leafs should jump on him. With a career 2.70 GAA and .912 SV%, Jarry is an above-average goaltender and someone who would be a better option than re-signing Ilya Samsonov.

If you were to pair him alongside Joseph Woll, that could be one of the best goalie tandems in the NHL. Currently making $5.375M until 2028, Jarry’s contract is very affordable for a starting or 1A/1B goalie, so Toronto should be very interested in him.

Pittsburgh has their own salary-cap issues, so trading him straight up for Marner wouldn’t work, or wouldn’t be fair value, so I’d expect something like this to make sense. Mitch Marner in exchange for Tristan Jarry, Marcus Pettersson, 2025 First Round Pick and 2026 First Round Pick (*if he re-signs).

Toronto would be shedding Marner for a number-one goalie, a top-four defenseman and two first-round picks, which seems like fair value for a player who may not re-sign here in one year from now. Sure, this trade wouldn’t add any offense in return but you would be getting a starting goalie and a big defenseman who can move the puck well.

Any Marner trade is a loss for the Leafs, but this is one that could help both teams and give Crosby an unbelievably skilled winger to play with every night and wouldn’t hurt the Penguins too much, if they do in fact re-sign Alex Nedeljkovic.