Few public officials – with the possible exceptions of Louisiana Gov. Huey Long and Boston Mayor James Curley – have politically survived so many flagrant run-ins with the law and polite society for so long as Washington's Mayor Marion Barry.

The nation's capital had been abuzz with reports of the mayor's possible use of illegal drugs and numerous extramarital affairs for years before a January 1990 FBI sting aimed at Barry finally revealed the truth for all to see. While the police operation seemed like entrapment to some, Barry was arrested at the Vista International Hotel after he indisputably bought and smoked crack cocaine with a longtime paramour turned informant.

The FBI filmed the incident to convince doubters, not to mention a federal grand jury, which indicted Barry on a cluster of cocaine and perjury charges. Despite the admission by Barry's own lawyer that the mayor had used drugs, a deeply divided, racially mixed jury deadlocked on most of the counts in August 1990, convicting Barry of a single misdemeanor charge of cocaine possession.

The case badly strained race relations, and local African Americans directed their ire not just at white prosecutors but also at white-owned media, especially The Washington Post, which had been strongly critical of Barry.

Barry was sentenced to six months in prison and lost both his position as mayor and his city council seat. But he won back a council seat in 1992 and was reelected mayor in 1994.