Having been a high-ranking lawyer in the U.S. Department of Justice in Washington, D.C., before that, Giuliani first gained national prominence as the federal U.S. Attorney for the Southern District of New York. In that position he prosecuted numerous high-profile cases, including indictments of leading Wall Street figures Ivan Boesky and Michael Milken for insider trading. Giuliani attracted some criticism for arranging very public arrests of people, then dropping charges for lack of evidence instead of going to trial.
Giuliani first ran as the Republican candidate for mayor in 1989 but he lost the contest to succeed Ed Koch to Democrat David Dinkins. In 1993 he successfully ran against incumbent Dinkins in an election that divided the city, primarily on racial lines (especially after the intervention on Dinkins' behalf of President Bill Clinton).
In his first term as mayor, Giuliani pursued an aggressive and hugely successful policing policy resulting in declines in virtually every category of crime. Such policing efforts led to an increase in the distrust of police by blacks and other minorities. Among the better-known incidents of police brutality during the Giuliani mayorality are the killing of unarmed Amadou Diallo in a storm of 41 bullets and the brutalization of Abner Louima while in custody.
Giuliani pursued similarly aggressive real estate policies. The Times Square redevelopment project saw Times Square transform from a run-down center for businesses ranging from tourist attractions to peep shows to a high-price district filled with stores and theaters oriented towards families, including the MTV studios and a massive Disney store and theater. Giuliani throughout his term pursued the construction of new sports stadiums in Manhattan, a goal at which he did not succeed, though new minor league baseball stadiums opened in Brooklyn, for the Brooklyn Cyclones, and in Staten Island, for the Staten Island Yankees.
Giuliani, after being elected, avoided one-on-one interviews with the press, preferring to only speak to them at press conferences or on the steps of City Hall. Giuliani made frequent visits to The Late Show with David Letterman television show, sometimes appearing as a guest and sometimes participating in comedy segments. In one highly publicized appearance that took place shortly after his election, Guiliani filled a pothole in the street outside the Ed Sullivan theater.
He ran an aborted campaign for U.S. Senate in 2000 against Hillary Rodham Clinton, withdrawing because of prostate cancer and the fallout from his relationship with Judith Nathan. (He was married at the time to Donna Hanover, but they later divorced, and in late 2002 he became engaged to marry Nathan. He and Hanover have one son and one daughter.) He married Judith Stish Nathan in May 2003.
Since the September 11, 2001 Terrorist Attacks on the World Trade Center, Giuliani has been widely hailed for his calm and effective leadership in the crisis. For this, he was named TIME magazine's Person of the Year for 2001 and was given an honorary knighthood by Elizabeth II of the United Kingdom on February 13, 2002, entitling him to style himself "Rudolph Giuliani KBE".