He’s coming to an end of a $100 million contract plus endorsements. If he values winning over money, he’ll leave money on the table so there’s room to sign players to get them over the hump. If he values money over winning, then the team is what it is.
I think he’ll sign but it won’t be for 8 years, it’ll be more like 4 or 5. If they win a cup or two over that time and are still contenders, maybe he extends. If not and the team regresses, then he asks for a trade.
Other posters can laugh and scoff but the above is for not anyways, either way. As long as Gary is commissioner, a Canadian team has no hope in winning it. They’ll make the finals but no closer.