F. Lee Bailey, the superstar lawyer who was part of O.J. Simpson’s defense team, has filed for bankruptcy in federal court in Maine in an attempt to discharge a federal tax debt of nearly $5.2 million, the Portland (Maine) Press Herald reported today. Debts to the Internal Revenue Service are not normally discharged in bankruptcy proceedings, but Bailey said on Friday that they can be after a period of time and as long as he has complied with certain conditions, such as filing and paying his taxes on time since the original taxes and penalties were assessed. He owes the money from a dispute over his reportable income from 1993 to 2001. Bailey was disbarred in Florida in 2001 over his handling of shares of stock owned by a client who pleaded guilty to drug smuggling and money laundering. That stock also led to the dispute with the IRS, which said Bailey owed $1.9 million because of his failure to report some of the stock proceeds as income. With interest and penalties, the IRS filed liens against Bailey totaling $4.5 million, which has since grown to nearly $5.2 million.
