9. Scottie Pippen
As you likely well know Scottie Pippen spent his entire career playing second fiddle to the greatest baller of all time, Michael Jordan. It wasnt a bad place for him to be in, though! In an era when contracts werent as lucrative as they are today, Scottie managed to rake in a whopping $120 million. However, he hasnt been wise with his financial decisions since retiring and has largely blown through his savings. Whoops!