Former coach touches on why Nylander is so tough to negotiate with

"I really don't think William is going to take a hometown discount," said Boudreau. "I only say that because I had his dad Michael and he held out and looking at his last contract, he held out. I think he has a value of what he thinks he worth and that he's going to get it."

It's not inside information, but Boudreau has known the Nylander family for a long time and he knows how stubborn Michael Nylander was when it came to his contract negotiations, so suggesting that it runs in the family is not a stretch by any means. Although Bourdreau didn't mention it, the other factor here is that Nylander is represented by Lewis Gross, who has a history of holding a player's current team hostage and walking his clients to free agency (see Johnny Gaudreau for an example). You can bet that Brad Treliving does not want to go down that route again so if no extension is in place soon, Nylander could find himself in another jersey come opening night.

In discussing Nylander's situation, Boudreau also touched on Auston Matthews extension saying, "And Auston, take him as long as you can get him. If you can get him for 8 years sign him for 8 years. If you can only get him for 3, sign him for 3. When healthy and he wants to play, he's a top 3 player in the league and maybe higher."

We know that it is highly unlikely Matthews signs for 8 years, but Boudreau is right. Whatever term Matthews approaches the Leafs with, they should at least consider it, depending on how flexible the 25-year-old is on the salary attached. It doesn't mean he doesn't want to stay, it means he is setting himself up to cash in on a bigger contract when the cap rises to new heights over the next few seasons.