The same person is eligible to win that award year after year after year.
I mean c'mon! How much would PHUN FUN fun would that be to have contestants vying for that prized prize? Having it be an ENORMOUS monetary prize would bring out all the seedy needy greedy money-hungry hoors and we could celebrate them for their despicabliity as well as their avarice. Why not? What could it hurt? Everyone says so.