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1999 Chicago mayoral election

The 1999 Chicago mayoral election took place after Richard M. Daley, the incumbent, decided not to seek a third term. Carol Moseley Braun, a former U.S. Senator, ran as a Democrat and was a prominent contender. However, Daley's brother, William M. Daley, entered the race as the Democratic candidate, leveraging strong political connections. The election primarily became a contest between William Daley and independent candidate Ray Wardingley. William Daley won comfortably, becoming Chicago's mayor and continuing his family's political legacy. The race highlighted Chicago's deeply ingrained political network and the influence of established political families.