Insider shares some good news and bad news on Matthews and Nylander extensions

"I'm not convinced Matthews signs by Saturday but everyone here is convinced he will sign. The Leafs have an idea of what the number is and what it's going to be. I think it's going to be 4-5 years. I think the number comes in around $13M," Friedman hypothesized.

The good news here is that the Leafs and Matthews' camp are far into contract talks and both sides have an understanding of where each other are on terms and dollar amount. It is no surprise that Matthews is going to become the NHL's highest paid player. Signing a 4-5 year deal allows him to collect one final and massive payday at the end of this extension that will take him to the end of his career.

Unfortunately for Leaf fans, Friedman did not deliver the same positive news when it came to Nylander's extension.

"I don't think there's a handle on Nylander yet. They've exchanged numbers but they're not close. What is the Leafs' comfort level with Nylander? There's a lot of work to do on this contract. They wanna keep him. There isn't any doubt about that. The other thing is that no body on this team has taken a cut. Everyone's maxed out and that's where Nylander is going say 'why should I if no one else is?', but I think it starts with a 9."

Friedman makes a very good point in that Marner and Matthews had not taken a major discount on their current contracts and with Nylander coming off of a 40-goal, 87 point season there is no reason for him to take a pay cut either to stay in Toronto. Friedman also mentioned the Leafs would like to have Nylander sign for under $9m per season, but that will be difficult.

It has been and will continue to be a busy few weeks for Treliving as he tries to fill out the roster around the "Core 4" and get contracts done for Nylander and Matthews, but we shouldn't expect either of those to be done on Saturday when they are both eligible to officially sign them.