9. O.J. Simpson
We all know about Simpson’s legal woes. The former NFL star’s landmark murder investigation trial and subsequent armed robbery conviction years later cost him millions of dollars. After initially walked free, Simpson expected to return to his old life. However, he soon discovered that it wasn’t that easy. He became a social pariah and this severely damaged his earning potential.
Furthermore, the judge ordered him to pay over $35 million to the victims’ families of the people that he definitely didn’t murder. While he is technically in the hole for this, he may never actually pay because of Florida. State laws enable him to keep his home from creditors and enjoy his NFL pension as well as social security payments. It could have been much worse for the notorious former star.