1. Michael Jordan
Jordan married Juanita Vanoy in 1989 and stayed married for two years. However, two years into his marriage he was already allegedly paying $250K in hush money to mistress Karla Knafel. When the divorce decree was final in 2006, Juanita reportedly received over $150 million dollars in settlement. This made the Michael Jordan divorce the most expensive in entertainment history to date, topping the splits of Steven Spielburg ($100 million), Kevin Costner ($80 million) and Sir Paul McCartney ($60 million).
