Friedman on Nylander, Leafs: 'I don't think they're that close'

The Toronto Maple Leafs landed John Tavares to open free agency, but the team still hasn't been able to lock up core pieces like restricted free agent William Nylander to a new contract.

The 22-year-old Swede was one of several topics asked of NHL Insider Elliotte Friedman during a Thursday afternoon radio hit on Calgary’s Sportsnet 960.

“I don’t think they’re that close,” indicated Friedman. “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 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.

“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.”

The Leafs signed Tavares to a seven-year, $77 million contract July 1, and Friedman alluded to both Auston Matthews and Mitch Marner being eligible to sign contract extensions with each player in the final season of his contract.

As Thursday’s radio segment continued, Friedman was asked about the challenge facing general manager Kyle Dubas in projecting getting those three young talents under contract.

“I would assume by now he’s got a pretty good idea of what it’s going to cost him,” said Friedman. “I do think they’ve talked with all three representatives because Marner and Matthews are eligible to sign extensions. So I do think he has an idea of what they’re all looking at.

“I’m sure Toronto’s pitch is, ‘Look, John Tavares left a lot of money on the table.’ He probably left about close to $15 million on the table from San Jose, and when you factor in the Islanders could have offered him the eighth year, what are we talking about here - maybe 20?

“So I think their pitch is going to be, ‘Look, John Tavares took less than he could have to play here, and if we’re going to win we all have to do that.’

“I said on radio in Toronto yesterday the one thing that’s kind of out of their control was Matthews had the agent switch right before, and you never know how that’s going to impact everything.

“I just think that you’re in a situation where you’re trying to say to guys, ‘One guy took a bit of a paycut, now we’re all going to have to do it,’ and you have to negotiate all of that.”