What will it take for him to re-sign? 4 years? 5? 6? more? How much will it take in $$$? 5m per year? 6m? 7m? more? He will be 33 when he starts playing for that contract. I think Chevy bends way over to re-sign him up to a certain point. He has proven with Ladd that he won't overpay older players, captain or not. I'd give him 7.5m x 4 years if he signed this summer but I doubt he takes that. How much is too much? How much would his ask be before you say trade him? When do you trade him? We could be in a similar spot next year. Do you trade a Blake Wheeler from a cup contending team? Chevy will earn his money in the next two off seasons, that's for sure.