A system and method for conducting a lottery for at least one item are provided. The method includes, for each of a plurality of buyers, receiving a buyer's declared valuation for each of at least one item being offered in a lottery by a seller, the item having an assigned non-deterministic probability of being allocated to the buyer, providing insured prices for outcomes of the lottery which are a function of the buyer's declared valuation of the at least one item, randomly drawing an allocation of each of the at least one item to a respective one of the buyers, based on its assigned non-deterministic probability, and allocating the insured prices to the buyers based on respective outcomes of the random drawing.