Rudolph Giuliani, 2000 News

New York City mayor, withdrew as N.Y.'s presumed Republican candidate for the U.S. Senate in May, after a turbulent few weeks in which he announced that he's battling prostate cancer, separating from his wife, Donna Hanover, and relying on the emotional support of “a very close friend,” Judith Nathan, a single mother. Long Island congressman Rick Lazio quickly stepped up and replaced Giuliani in the Senate race against Hillary Rodham Clinton.