"He's put the money in the bank to set his family up for a long, long time. For him, he can look at shorter deals. It leaves flexibility for him to not get locked into a bad situation.
If the cap keeps going up and up and he remains a top player in the game, that'll be beneficial for him financially. I'm not going to say an 8-year deal can't happen, but it doesn't seem likely. He's more inclined to take something in the mid-range, whether that's 3, 4, or 5 years.
It's in the Leafs' best interest to get him signed as long as they can because of what he means to the Leafs, and Shanahan has said in the past he would like some of these guys to be lifelong Leafs. So the Leafs will pitch him on an 8-year deal, but I think it'll be a tough ask at this stage because he's already made that money, and no one knows how much the cap is going up."