Abstract: A system and method for conducting a lottery operate by offering a lottery ticket at a price that is somewhat higher than the price of a standard lottery ticket. All or some of the extra amount is used to pay a premium on an insurance policy or otherwise fund a tax reimbursement pool that will be used to reimburse any lottery winner or winners who purchased the higher-priced ticket for at least a portion of the amount of taxes withheld from the prize winnings. In the event that the tax reimbursement is considered income of the winner under applicable law, the winner could also receive a second reimbursement for the tax on the amount of the first tax reimbursement. A reiterative tax reimbursement cycle could, but does not necessarily, continue until the tax liability of the winner is merely pennies.