Treliving will look to avoid a Gaudreau situation, likely to move a member of the Core 4 before risking free agent walk
Even before Brad Treliving took over as the Leafs' new GM, all of the talk was about Auston Matthews and his extension. There was some chatter about William Nylander's contract status as well, but compared to Matthews', the Nylander chatter has been minimal.
Now that Treliving is GM, however, discussions around a Nylander extension have picked up, but not for the right reasons. Last off-season Treliving went down to the wire trying to negotiate a new contract for Johnny Gaudreau before he bolted to Columbus. Gaudreau is represented by Lewis Gross, who also represents Nylander. Nylander's last extension went down to the final minutes of December 1 in 2018 before he would've been ineligible to play that season. A deal was struck within minutes of that deadline and now, Nylander's deal looks to be a steal. Now entering the final year of that deal, negotiations will begin on another extension.
Given what Gross put Treliving, the Flames and Flames fans through last off-season, you can be sure that he will not let it happen with Nylander this off-season. If Nylander isn't signed to an extension this summer, you can almost guarantee that Treliving will trade the Leafs forward, as The Athletic's James Mirtle points out, to recoup some assets instead of letting he and his agent, Lewis Gross, do what Gaudreau did last year.
