Since the Leafs were eliminated by the Florida Panthers in the second round of the playoffs in May, much of the off-season has been spent wondering if and when Auston Matthews and William Nylander will sign extensions. As far as we know, the Leafs and Matthews have been much closer than the Leafs and Nylander, but we still await the moment pen is put to paper.
After a lengthy hiatus, TSN's Chris Johnston returned to his podcast "The CJ Show" and provided a bit of insight into the Matthews and Nylander extensions. Johnston said over the last month that it has been fairly quiet between the Leafs, Matthews and Nylander. CJ stated that he believes Nylander is hesitant to be the first to sign again due to the pay gap that arose the last time he, Matthews and Mitch Marner signed extensions one after another. He reiterated that Matthews is going to sign, but wants to win and is figuring out the best way to help the Leafs do so.
CJ believes that the Matthews extension will very likely occur very close to the timeframe thaf Nathan MacKinnon's extension was announced last off-season, signing on the eve of training camp. Neither Matthews nor the Leafs want to enter training camp with all of the Toronto media fixated on his extension talks.
From what CJ has reported, it would not be surprising if Nylander signs shortly after, once he sees Matthews' cap hit so he can better position himself. As long as Nylander isn't married to the idea of locking down a deal for $10M+, perhaps we'll see both deals announced before training camp gets under way.
