Who

New York's combative, controversial former mayor watched his bid for the presidency go up in smoke earlier this year. Don't shed any tears: As long as Rotary Clubs in the Midwest are willing to pay him big bucks to hear about his "heroic" exploits on Sept. 11th, he shouldn't have any trouble paying Judi Nathan's credit card bills for the foreseeable future.

Backstory

Rudi Giuliani has never hesitated to point his finger at the bad guys—except, that is, when members of his own family are involved. Rudy's father, Harold Giuliani, was a low-level enforcer for the mob in the '50s and served time at Sing Sing for robbery and felony assault. (The former mayor has never acknowledged his father's criminal past, describing his dad as the ''finest man'' he has ever known.) Brooklyn-raised Rudy pursued a different path, of course: He briefly considered the priesthood, but decided to enroll in law school and went on to clerk for a federal judge, successfully dodging the draft before joining the U.S. Attorney's office. After a brief stint in private practice—and after conveniently changing his party affiliation to match that of the sitting president—he was appointed U.S. Attorney for the Southern District of New York, gaining widespread attention in the '80s as an aggressive young prosecutor in pursuit of organized crime figures and white-collar criminals.

Giuliani took his first shot at elected office in 1989, running against David Dinkins. He lost by a slim margin, but was luckier his second time around. In 1993, he ran on a platform that promised law and order and economic growth to a city still reeling from the Crown Height riots and a sharp recession. Giuliani prevailed and he spent two controversy-packed terms as the city's chief executive. With term limits preventing him from seeking a third term, in 2000 he decided to take on Hillary Clinton and run for the Senate. A diagnosis of prostate cancer forced him to abandon the bid, and he spent the better part of his last year in office on the front page of the Post, tangled in a messy divorce with his wife Donna Hanover. Of course, everything changed after Sept 11th. A day before, his approval rating was below 50 percent and his political future was in doubt. Within weeks of the attack, he'd been dubbed him "America's Mayor" and had been named Time's "Man of the Year."

Of note

Half a dozen books have been written about Giuliani's legacy as mayor, and pundits continue to debate how he measured up on the job. Rudy's supporters will tell you he cracked down on crime; his detractors will tell you that the drop in crime pre-dated his arrival at City Hall, was part of a broader national trend as the crack epidemic petered out, and that whatever success the city had during his administration had more to do with the tactics employed by police commissioner Bill Bratton than anything else. Fans of the former mayor will argue he improved the economy and made the city livable again. Critics will tell you that New York's economy improved thanks to the stock market boom in the '90s and that his focus on quality-of-life issues inflamed racial tensions and violated civil liberties. Rudy's supporters say that he cut the welfare rolls, slashed taxes, and was an incorruptible leader. More fair-minded observers will tell you that he left New York with a gaping deficit when he left office and will rattle off a long list of people who earned city jobs thanks to their ties to the mayor, the most obvious example being Bernie Kerik, his former driver who served as police commissioner until he resigned in disgrace.

Even his actions following Sept. 11th have long been in dispute. Rudy talks about "bold leadership" in the aftermath of the greatest attack on U.S. soil. Yet critics have pointed to countless examples of how his leadership was lacking both before and after the attacks, citing examples such as his decision to place the Office of Emergency Management in the World Trade Center even though his closest aides had warned him against the idea. But 9/11 allowed Rudy to reinvent himself. And the brand new storyline allowed him to reinvigorate his declining political fortunes.

After leaving office, Giuliani spent several years exploiting his newfound cred as the founder of a consulting/lobbying/banking firm, Giuliani Partners and Giuliani Capital Advisors, assembling a personal war chest of more than $100 million in the process. In 2007, he sold his stake to launch his bid for the presidency and embarked on the sort of campaign that he assumed would appeal to Republican voters—he focused on law and order, the battle against Al-Qaeda and illegal immigration, and touted his accomplishments cleaning up the cesspool that was once New York with the promise he'd do the same for the rest of the country. Giuliani's fear-laden campaign got off to a solid start and for much of early 2007, he was the GOP front-runner. But his candidacy toppled as primary season got underway. Perhaps his shifting positions on social issues (such as abortion, gay rights, and gun control) did him in. Or the noticeable unease he displayed on the campaign trail.

Or maybe it may had had something to do with the very frequent, very embarrassing personal revelations that seemed to pop up at every turn. Indeed, his first humiliation came before he'd even officially entered the race, when an internal document, detailing many of the reasons why he was unelectable, surfaced. Embarrassments continued to dog him on the campaign trail: There was a series of stories about his wife, Judi Nathan, his "expert on chemical disasters," and the six spouses between the two of them; the fact that his daughter suggested she was voting for Obama and that his own son wasn't on speaking terms with him; and the revelation that he used taxpayer money to go on weekend trips with Nathan to the Hamptons when he was still mayor.

Giuliani mercifully abandoned his scandal-plagued campaign in January 2008. He's now back to his old tricks at Bracewell Giuliani, the Houston-based law firm where he's a partner. And once again he's working with his old pals at Giuliani Partners, where the company directory resembles the City Hall phone list circa 1999—execs include Peter Powers, Rudy's onetime deputy mayor; Michael Hess, his former corporation counsel; Daniel Connolly, another Giuliani administration lawyer; and Anthony Carbonetti, his former chief of staff.

Rudy's back to doing what he does best: Collecting checks from the highest bidder and taking on assignments that hardly fit his image of righteousness. His firm has represented Citgo, the oil company controlled by Venezuelan President Hugo Chavez; it also was advising a casino enterprise controlled by Hong Kong billionaire Stanley Ho, who has ties to organized crime in China as well as North Korea's Kim Jong Il. And when Rudy feels like stepping out of the office, there are those $100,000-an-hour speaking gigs. Forbes estimates Giuliani collected $8 million in 2006 from his speaking engagements alone.

Personal

Giuliani's personal life is a complicated saga. His first wife was Regina Peruggi, who also happened to be his second cousin. Although they were together for 14 years, Giuliani had the marriage annulled by the Catholic church based on the claim that he hadn't known she was related to him, or that he didn't know it was a violation of church rules. (He's given differing answers over the years.) He proposed to his second wife, TV personality Donna Hanover, before his divorce from Peruggi had been finalized. With Hanover, he had two children, Andrew and Caroline.

Giuliani and Hanover's relationship crumbled when the mayor admitted to his affair with Judith Nathan in 2000. (Rudy classily announced they were divorcing at a press conference.) But the truth is, Rudy was having affairs long before Nathan came along. He had an affair with his secretary when he was married to Peruggi, and was involved with Cristyne Lategano, his former communications director, during his marriage to Hanover. It was the affair with Nathan, though, that led to a messy legal battle, and it took more than two years for Hanover and Giuliani to reach a divorce settlement. He married Judi, his third wife, on May 24, 2003. Mayor Bloomberg presided over the wedding, which was held at Gracie Mansion.

Habitat

Giuliani and Nathan live at 45 East 66th Street, the same building that's home to Nina Garcia. They also have a weekend home in Water Mill—which features a pool, wine cellar, and cigar room—and a condo in Palm Beach. They live alone: Both of Giuliani's two kids have strained relations with their step-mom and barely speak to their father. The daughter whom Judi adopted in the mid-1980s, Whitney, lives with her father.

For the record

Much of the sorid nitty gritty of Giuliani's life can be found in Village Voice reporter—and longstanding Rudy antagonist—Wayne Barrett's Rudy!: An Investigative Biography of Rudolph Giuliani. Other books in the Rudy canon include Andrew Kirtzman's Rudy Giuliani: Emperor of the City and Ed Koch's Giuliani: Nasty Man.