If he's after every last dime he can make, he'd be better off signing short term (1-2 years) and then getting a new max/supermax deal. Yes, he'd sacrifice some security, but, since maximum term of a contract is only 4-5 years, not very much. In the NBA, just like in the NHL, max/supermax deals are tied to percentage of the cap. And the cap in the NBA has been increasing like crazy. The difference between the two leagues is that NBA stars get max deals routinely, where as we haven't seen it happen in the NHL yet.