Reports are surfacing that negotiations between William Nylander and the Toronto Maple Leafs could drag into September and the two sides aren't close on a new deal that would keep one of the four young forwards in Toronto for the foreseeable future.

NHL insider Elliotte Friedman recently noted he felt the Toronto Maple Leafs and forward William Nylander are still a ways apart on a contract extension for the young winger. Friedman was on Sportsnet 960 this past Thursday and noted that a number of articles had been written about this negotiation dragging into September and he suggested that might be accurate.

Friedman seems to think the biggest hurdle is the pending decision to sign Nylander to a bridge deal or long-term contract. He explained, “If I was Nylander, I might be the kind of guy who would bet on a bridge deal," likely suggesting as such because there is every indication Nylander could have one or two really strong seasons in Toronto and boost his value. Friedman added, "But I think Toronto has kind of tried to negotiate the waters with three guys at once, and it’s not easy.”

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The risk for the Maple Leafs is signing Nylander to a short-term deal and then him exploding offensively playing alongside Auston Matthews. Should Nylander hit 70-80 points, he might price himself out of any salary Toronto can afford. Friedman then speculated the Leafs are trying to avoid this situation and trying to navigate how to keep all four guys — Nylander, John Tavares, Auston Matthews and Mitch Marner. When it came to Nylander, the statement was, "the last I'd heard, it wasn’t that close.”

The only chance GM Kyle Dubas has of keeping his young core together is by explaining to the three remaining future signees that Tavares potentially left $15 to $20 million on the table to sign with the Maple Leafs. If he can convince them to do the same, perhaps Toronto can keep everyone. That process has to start with Nylander.

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