Bad news for the Maple Leafs on the Nylander front.

This may be big trouble for Toronto.

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The Toronto Maple Leafs may have a serious problem on their hands and that problem may come in the form of talented forward William Nylander,

There has been a ton of talk around the Toronto Maple Leafs big 3 young young forwards, the aforementioned Nylander as well as Auston Matthews and Mitch Marner, and how exactly newly appointed Toronto Maple Leafs general manager Kyle Dubas expects to fit all three of them under the cap. Earlier this month Nylander himself expressed doubts during the National Hockey League's European Player Media Tour and that may have been the first sign that things were not as good as Leafs' management would have you believe.

On Thursday Sportsnet insider Elliotte Friedman was asked about the progress the organization has made in the contract negotiations with Nylander and it was the first time that I can remember an NHL insider indicating that there may be a very real roadblock here. According to Friedman the Leafs' are hoping their young stars will take a discount much in the way that star center John Tavares did by signing in Toronto for $11 million per season, but Nylander is understandably looking to get paid.

“I don’t think they’re that close,” said Friedman as per Nichols on Hockey. “I’m always scared about answering that question because I’ll say I don’t think they’re that close and then I’ll hang up they’ll be done and it’ll be evidence No. 3,246 that Friedman’s a tool, so I always worry about that.

“The last I heard, they weren’t that close. There’s been some articles around here written that don’t be surprised if it goes into September. He’s represented by Lewis Gross, and you guys remember that two years ago it was about now actually that the [Johhny] Gaudreau-Flames stalemate ended, and Gross is a Gaudreau guy. So it’s about there. I think it’s something that could go into September.”

There's an extra little wrinkle in here that wasn't touched on by Friedman and that is the current perception of the contract Gaudreau signed with the Flames. Many felt at the time that the Flames had overpaid for a young man with very little negotiating power, but given the current contracts being handed out around the league Gaudreau's deal now looks like a gigantic bargain. Gross is likely very aware of this and will likely look to avoid a similar mistake with Nylander, something that could cost the Leafs.

Perhaps the most damning comments Friedman however where the big picture comments he made regarding Toronto's big 3. Although Dubas has gone on record again and again indicating that he can and will sign all 3 players, it seems there is now some real concern regarding whether or not they can do so.

“To me the biggest question is are we talking a bridge or are we talking term. If I was Nylander, I might be the kind of guy who would bet on a bridge deal. But I think Toronto has kind of tried to negotiate the waters with three guys at once, and it’s not easy. There are four guys - with Tavares - they’d all like to keep, but I don’t think it’s always the easiest thing in the world to do it.

“But the last I’d heard, it wasn’t that close.”

Not good for the Maple Leafs.