Yeah there's some kind of insurance you can buy that covers potential losses due to contests. I never knew about it until I read the article about the guy in Chicago. It does make sense though. How many contests would huge corporations like McDonald's or Coke have if there wasn't a way to recoup the losses? It's not like they need the publicity.
The same type of insurance is used at golf tournaments. You know the case where the prize for a hole-in-one is a car, etc. Same thing for the football through the tire at the bowl game for a million, the half court shot for the money, etc.