Disney World, Mountain bikes, a full kitchen of black and decker appliances, free tires, $100 of groceries...
He would also enter his friends and family into them too. His sister also won the black and decker appliances from one of his entries for her.
He actually won the Nintendo 64 console I have.
He would sit in the back of the chapel, or high priest class and fill out 3x5 cards with names and addresses during church. Lots of people thought he was taking notes...but he was prepping his sweepstakes entries.
He got a regular sweepstakes newsletter and would go through and highlight the ones he thought were worth entering.