The Toronto Maple Leafs have maintained signing William Nylander is a priority. But with an extension not yet finalized, there’s a chance Nylander is holding out with a desire to test free agency. As Nick Kypreos and Justin Bourne (and guest Sam McKee) discussed during a recent show, Nylander’s agent, Lewis Gross might be advising waiting. “…maybe they just want to go to UFA,” McKee argued.
Bourne added that Gross’ clients have a history of going to free agency. Only an overpayment for Nylander might avoid that now. It poses not just a short-term problem as it pertains to Nylander. The situation could linger longer term regarding the future of Mitch Marner.
There is more at risk here than just losing Nylander, suggests the two hosts. Bourne explained the scary part is that the Leafs could lose both Nylander and Marner. The team might be alright with losing one, but not both. He notes:
“…if you lose Willy Nylander, like let’s say you’re like okay, we value the cap space or we were going to trade him at the deadline, or whatever, if you don’t have Nylander on your roster, and then it’s Mitch Marner’s turn for negotiation. You’re screwed, because you can’t lose them both.”

He adds that losing Nylander gives Marner all sorts of leverage. “Mitch has you up against a wall at that point where you’re saying we gotta keep one of our elite wingers, our game breakers, our guy who plays the most minutes, you know, and so that changes things were …”
Would Marner use that in negotiations to secure himself a better deal? His agent would undoubtedly play that card.
Should The Maple Leafs Trade Nylander for a Winger Then?
Ideally, signing Nylander solves the problem of losing him and Marner playing the loss against the team. It keeps the core intact and means the club won’t have to scramble for replacements. But if that isn’t in the cards, GM Brad Treliving has a decision to make.
If a deal can’t be reached between the Maple Leafs and Nylander, should Treliving focus on replacing him in trade with a winger? Not only would that help replace the player going out, but it potentially limits some of the negotiating power Marner might have. If they believe Marner holds the team over a barrel it might be a smart strategic move to make it so he can’t argue that if Toronto already has another winger ready to go.
Then again, going that route potentially leaves the Leafs with holes in other areas of the roster.
Next: Maple Leafs May Move Around Max Domi to Upgrade Center Depth

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