Is Brock Lesnar the smartest businessman in the history of the industry? Given his current payouts, the way he's always done whatever the hell he want, I think it's a given. Even when it's not been especially good for business (New Japan) he's held the main title and gone over. The argument is made that Lesnar would lay down for anyone, yet he rarely does.
I still feel like Hogan is, for maintaining that level of money day in and day out for nearly a decade even when all he had to offer was smoke and mirrors. Brock made some really dumb business decisions for a while there, whereas Hulk would still be a multimillionaire many times over if not for his divorce and assorted lawsuit issues. Hulk managed to convince WCW to pay him 25% of PPVs that he wasn't even on! You have to respect that a little.