Something the Leafs' new GM said, or didn't say, to the media last week could blow back on William Nylander

Something else Treliving mentioned on Thursday is also interesting. He mentioned that he has a good relationship with Matthews' agent, Judd Muldaver. He did not say the same or mention anything about Nylander and his agent Lewis Gross. That is likely because his relationship with Gross is strained after the Johnny Gaudreau contract debacle last off-season. Gaudreau is another of of Gross' clients and said that he wanted to stay in Calgary the entire season and up to the very last moment during negotiations before taking less money than he was offered in Calgary and bolting to Columbus instead.

Gaudreau and Gross left Treliving in a difficult position in Calgary and likely tarnished their relationship to an extent. It would not be surprising if Treliving goes into negotiations with Nylander skeptical that a deal even gets done after what happened last off-season. It also means that Treliving could avoid having another Gaudreau situation and deal Nylander before his modified no-trade clause kicks in on July 1st.

While it would be a huge loss for the Leafs' top-6, the return for Nylander could yield them a fine return and could free up more cap space to add a pair of middle-six forwards to the group. It will be a very busy month for Treliving as he decides what his plan for the future of the Leafs will be and whether or not he wants to go down the road of tense negotiations with Gross again.

There's also the matter of what Nylander will want on his next deal. Obviously, the near $7M per season he's making now would be a pipe dream for the Leafs on his next deal. Given where he finished this year, with 87 points, that total sits just 7 points back of where Mitch Marner finished back in 2019 just a few months before signing his massive 6-year deal worth a staggering $10.893M per season (which then inflated to $10.9M when the league minimum salary increased). As such, it wouldn't be an unreasonable request from the Nylander camp to pursue a deal between $10M and $10.5M - especially with the cap expected to rise by a much larger denomination than normal next summer.

With Lewis Gross often squeezing teams for every last dollar, Treliving may just want to wash his hands of that entire situation. It shouldn't come as a surprise to anyone if that's exactly what he does.