Michael Jordan & Juanita Vanoy: ~ $168 Million Settlement

Former Chicago Bulls star player Michael Jordon got married to former model Juanita Vanoy in 1989, during his second season. By 2002, there were rumors swirling that they were splitting up. The pair tried making it work for 4 more years, before finally divorcing in 2006.

Media started speculating that he cheated on her plenty of times, and she was done with his philandering ways. However, in a joint statement, the couple said that they had mutually and amicably decided to split up. So, 17 years of marriage cost Jordon $168 million in settlement plus $2.1 million in only legal fees!