19. O.J. Simpson
After going on trial in one of the most infamous murder trials in U.S. history, the wisest thing to do would be to keep your head down. A court controversially acquitted Simpson and gave him a second chance. However, the former football star couldn’t stay out of trouble. In 2007, Simpson and a group of friends burst into Bruce Frumong’s Las Vegas hotel room and held him up at gunpoint.
Simpson alleged that Frumong had stolen some of his sports memorabilia. However, the victim, a dealer in such items, denied this, and a court sentenced Simpson to 33 years in prison for his actions. After serving for nine years, Simpson finally walked free in 2017. In sum, it was extremely foolish of him to give the court an opportunity to lock him away. They obliged happily.