Once he was considered to be one of the most brilliant lawyers in modern times, now 20 years after he helped set O.J. Simpson free, he has fallen considerably. Although Bailey is now 84 years old, many legal professionals speculate that he would still be practicing law, if hadn’t been disbarred in 2003. Bailey has filed bankruptcy more than once since the ‘trial of the century.’ He’s currently working in a small office above his girlfriend’s beauty salon in Maine. He was disbarred in both Florida and his native Massachusetts, in 2001 and 2003.
The charges that got Bailey disbarred ranged from petty theft to defrauding a government entity. He tried several times to regain his law license, but was unsuccessful each time. Bailey said Simpson called in 2008 when he was arrested for the bungled hotel room robbery in Las Vegas. The football great wanted legal advise. Bailey being disbarred couldn’t really give him any. The Boston’s Stranglers former attorney told Simpson to fire all of his lawyers,”you’ll fry with that crew.” Simpson didn’t take Bailey’s advise and received a 33 year sentence.
Bailey believes anyone associated with Simpson’s criminal trial in 1995 is cursed, he calls it the ‘Simpson curse.’ Aside from Bailey’s problems, Johnnie Cochran died of a brain tumor in 2005 at the age of 67. Robert Kardashian died in 2003 at the age of 59 from esophageal cancer, after a very short battle with the illness. In 2005 Robert Shapiro’s son Brent Shapiro died of a drug overdose at the age of 24. Bailey owes more than 5 million dollars to the IRS for unpaid taxes, and filed bankruptcy as a reprieve from the debt. Bailey says the IRS has been relentless in their attempts “to get blood from a stone.”