How many terms did Marion Barry serve as mayor of Washington, D.C.?
Marion Barry served four terms as mayor, even though his third was marred in 1990 by a criminal case that by most measures should have ended his career. FBI agents had conducted a sting operation in which Barry and a girlfriend were arrested for drug possession. The arrest was caught on film and broadcast ad nauseum on television, as was the footage of the mayor smoking crack. Barry served six months in federal prison, and upon his release he ran for a city council seat, using the slogan "He May Not Be Perfect, But He's Perfect For D.C." He won his fourth term as mayor two years later.
SOURCE: Former Mayor's Victory Worries Many in Capital | New York Times