New York's 106th mayor—and first black mayor—Dinkins wrested the mayoralty from fellow Democrat Ed Koch in 1989, but lost his bid for reelection in 1993 to Rudy Giuliani following a gloomy term marked by the Crown Heights riots and out of-control crime.
Born in Trenton, Dinkins briefly served in the Marines and went on to Howard University and then Brooklyn Law School. A key political player in Harlem as one of the "Gang of Four" with Percy Sutton, Basil Paterson, and Charles Rangel, Dinkins served as the City Clerk for a decade before becoming the Manhattan Borough President in 1985. Then, in 1989, Dinkins mounted a surprise victory over three-term incumbent Ed Koch after Koch's administration was accused of corruption and for poorly handling racial issues. However, Dinkins' time in the Mayor's office was cut short due largely to the Crown Heights riots that loomed over his administration (even though crime rates largely declined during the last 36 months of his tenure). But the damage was done, and Rudy Giuliani came out victorious in 1993. Dinkins went on to become a professor in the Practice of Public Affairs at Columbia and is still actively sought after for endorsements in New York elections. [Image via Getty]