Cost: $20,000,000 

Evander Holyfield's craft involves repeated Mike Tyson upper cuts to the head, so we're not shocked by his inability to do simple math. The brain can only take so much bleeding. He bought a house that has 109 rooms, two bowling alleys, and costs $155,000 in annual taxes. Combine the cost of heating 54,000 square feet with child support for a dozen kids and you have an express pass to the front of the soup line. J.P. Morgan ultimately foreclosed on the palace and sold it at auction for $7.5M, a hit more painful than a James "Buster" Douglas roundhouse punch.