Popular radio host believes that Brad Treliving is using a brilliant negotiation tactic on Matthews, Nylander

"I'm just thinking here, maybe there's a chance the Leafs are the ones holding this up. That they're trying to convince him to change his mind on that. That Matthews has said 'I'll sign right now for 3 years, 4 years, whatever the price is' and it's the Leafs buying their time trying to convince him to come off that...There is a chance that could be what is happening here is Matthews is saying 'I'll sign right now for 3, 4, 5, years at this price' and the Leafs are saying 'can we meet up again and try to convince you for 6+ years?'"

The entire time that Matthews has been eligible to sign his extension, everyone has believed that he is the one holding things up and that he holds all the cards. While he may hold all or most of the cards, Brad Treliving has the experience that Kyle Dubas had lacked when negotiating with superstars and is showing it now in not giving into their first or second set of demands and offers to one another. There's an old saying, "if you have time, use it". It appears as though Treliving intends to use the time he has to ensure that he gets these deals right.

The Leafs and Matthews and Nylander will want to get these extensions sorted out before training camp begins to avoid the circus and having to answer questions about this all season long, becoming a massive distraction to the team and players themselves until they are signed. That's not a distraction that anyone needs in an important season, so maybe this is purely a negotiation tactic by Treliving to persuade Nylander and Matthews into blinking first.