When Rudolph Giuliani first ran for mayor of New York in 1989, he made a critical mistake. Assuming that he'd be running against the blue-collar, socially conservative Democrat Ed Koch, Giuliani cast himself as a liberal. Playing against his tough-guy image, he spent his first months on the campaign trail talking about the victims of homelessness and AIDS and drug abuse, causes that united elite liberals and poor minority voters while leaving the city's shrinking middle class cold. The prosecutor who brought down mob boss Anthony "Fat Tony" Salerno and Wall Street renegade Ivan Boesky tried to reinvent himself as...