Ten Things You Might Not Know About Rudy Giuliani

You may think you know a lot about Trump's star lawyer, but there are a lot of facts you probably never heard.
Published November 05, 2018 | 5 min read

“America’s Mayor,” as he was once called, has led a colorful, controversial life in public service and private enterprise.

Known as the nation’s most recognizable mob prosecutor, a hero to many New Yorkers following the Sept. 11 terrorist attacks, and now Donald Trump’s personal lawyer, Rudy Giuliani commands headlines, both for his admirable successes and execrable transgressions.

Now, with his emergence as a key player in the ongoing Trump investigations, Giuliani deserves fresh scrutiny.

Here’s our list of Rudy’s greatest hits:


Seizing on a disregarded crime-fighting law signed by Richard Nixon in 1970, one that was not intended to prosecute gangsters, Giuliani employed the RICO act to lock up New York’s most powerful wiseguys. Indeed, the first use of this legislation didn’t come until 1979, when Rudy’s predecessor at the Southern District of New York brought a financial fraud case against the longshoreman’s union leader. But Giuliani saw how the measure provided harsh jail sentences for those who committed multiple felonies — newly dubbed “racketeering” — and allowed the feds to confiscate assets. So he made it his weapon of choice, hammering the mob bosses of New York’s five families. His efforts culminated in the Mafia Commission Trial of 1985, which involved indictments, convictions or life sentences for virtually the entire gangland top echelon, including Gambino godfather Paul Castellano and the heads of the Bonanno, Lucchese, and Colombo families. Organized crime never recovered.


Giuliani’s prosecutorial success was hard to square with an astonishing revelation by the late great investigative reporter Wayne Barrett in 2000: Rudy’s father was a mob associate who served 18 months in prison for armed robbery after he ripped off a milkman at gunpoint in 1934. Harold Giuliani and an accomplice came across the delivery man as he was collecting payments from customers in an Upper East Side apartment building in 1934, pointed a gun at him and snatched $128.82 from his pocket, Barrett reported in the Village Voice. In the late 1940s, when Rudy was a young boy, his dad took a bartending job with his father-in-law, Leo D’Avanzo, who owned a tavern where he ran a loan-sharking and gambling operation. Harold, quick to throw a punch, carried a baseball bat when collecting debts for D’Avanzo, Barrett reported. None of this Giuliani talked about. For years, he pointedly avoided questions concerning his father, who decades earlier had lied to the judge in that robbery case, giving his name as Joseph Starrett. After the story broke, Rudy said of Harold, who died of prostate cancer in 1981 at age 73, “I miss my father every day of my life. And he’s a very, very important reason for why I’m standing here as the mayor of New York City.”


In 1968, a few months after Rudy got his law degree from NYU, he married a woman he’d known since childhood in The Bronx, Regina Peruggi, who was the daughter of his father’s first cousin. Rudy once claimed he didn’t know they were cousins. He later stated, wrongly, that they were third cousins. Either way, there’s nothing illegal about such an arrangement. Even first cousins can marry in New York. She and Peruggi, who was president of Kingsborough Community College until 2014, split in 1982 after 14 years of marriage. With the two being Roman Catholics, and the church being against divorce, the couple managed to get an annulment — by arguing that the church had never granted a dispensation for them, as second cousins, to wed.


When Rudy hired Bill Bratton to run the NYPD in 1994, he made a great choice. Crime, which had been soaring, dropped dramatically under the new commissioner, who employed crime stats and aggressive community policing to make the city safer. The only problem? Bratton became a media darling, which people close to the mayor recognized as a threat to the publicity-loving Giuliani. Rudy began to jab at Bratton behind the scenes, grilling him over his $350,000 book contract and reminding the police chief who was who’s boss. But the kicker? Time magazine put Bratton on a cover in 1996, under the headline, “Finally, we’re winning the war against crime. Here’s why.” The coverage infuriated Giuliani, and Bratton resigned under pressure after just 27 months on the job.


Long before the Black Lives Matter movement, police shootings of unarmed men of color shocked the nation, including in New York under Mayor Giuliani. One of the most galling involved Patrick Dorismond, a 26-year-old security guard and father of two who was off duty and enjoying a night out at a bar when an undercover officer approached and asked if he could buy pot from him. Dorismond got offended, loudly proclaiming he wasn’t a drug dealer, and a scuffle ensued, which ended when cop Anthony Vasquez fatally shot him in the chest. Amid the outrage that followed, Rudy, who was running for U.S. Senate, backed the cops and tried to demonized Dorismond, releasing his sealed juvenile record (which had one minor violation at age 13) and falsely claiming in a TV interview that the victim “spent a good deal of his adult life punching people.” He said Dorismond “was no altar boy.” That also was untrue. It turned out that 30 years after Giuliani graduated from prestigious Mayor-Bishop Loughlin high school in Brooklyn, Dorismond attended the same Catholic school. And served there as an altar boy.


Sure, it was all in jest, but this playful video clip of Giuliani, dressed in drag and pretending to be scandalized when the future president mashed his face into Hizzoner’s fake cleavage, comes off as not quite so funny in light of the claims of 19 women who say Trump sexually attacked or mistreated them. “Oh, you dirty boy, you!” his female alter ego, Rudia, exclaims. “I thought you were a gentleman!” The mayor loved the get-up — bouffant blonde wig and push-up bra — which he donned for performances at the Inner Circle talent show, in which members of the City Hall press corps and mayoral staff zinged each other with skits and musical numbers. He even reprised Marilyn Monroe’s sexy serenade to John F. Kennedy, “Happy birthday, Mr. President.” The mayor being comfortable with his girlish side endeared him to many New Yorkers, who cheered Rudy when he marched eight times in the city’s Gay Pride parade, and when he spoke admiringly of his gay couple friends with whom he lived in 2001 during marital troubles with Hanover. It didn’t last. Giuliani let down his same-sex supporters when he refused to back gay marriage, then put away his wig and gown for good, preferring $5,000 Brioni suits, a close-crop cut and designer glasses.


Thanks again to a Barrett expose, this time in his book, “Rudy! An Investigative Biography of Rudolph Giuliani,” the public learned new details about the mayor’s extramarital flings and his romantic bungling. “Rudy!” reveals that he’d hooked up with his mayoral press secretary Cristyne Lategano, after which his wife, Donna Hanover, slammed her as a homewrecker and forbade Lategano from any contact with their children. The lovebirds were hardly skilled at hiding their affair. They’d share sodas and pizza slices, and Lategano, just 28 when she got hired, would fuss over over his appearance, at one point telling her boss, “ ‘Oh, you look like a bunny rabbit,’ ” according to Barrett. On Father’s Day 1995, the two snuck into his City Hall suite for a three-hour rendezvous, just after Giuliani informed reporters that he was off to play some ball with his son, Andrew. Rudy also carried on a secretive affair with divorced nurse Judith Nathan, whom he later married. Barrett claimed that it was women, not Giuliani’s prostate cancer, that ended his bid for the U.S. Senate.


There were many reasons why New Yorkers turned against Giuliani, whose popularity sunk to a 40 percent approval rating in the year prior to 9/11, including the brutalizing of immigrant Abner Louima in a precinct bathroom and the shooting of unarmed Amadou Diallo. It didn’t help that Giuliani’s tax breaks for the rich and a slew of patronage hires saddled the city with millions in unnecessary labor costs and led to a $4.5 billion deficit. But the real turning point might have come when Rudy declared war on Chris Ofili, an award-winning artist from Africa known to incorporate dried elephant dung on his paintings. Ofili’s piece, “The Holy Virgin Mary,”  which hung at the Brooklyn Museum of Art, infuriated Giuliani, who called it “sick.” He vowed to cut off the $7 million in funding the city provided to the museum, a third of its total budget, unless they pulled it off the wall, and threatened to evict them. The museum filed a federal suit in response. Many in New York got angry that Rudy would intrude on artistic freedom of expression, and Giuliani took a beating in the polls. He was wrong about the painting’s worthiness. “The Holy Virgin Mary,” which before coming to New York had been purchased by Charles Saatchi and exhibited in London and Berlin, sold in 2015 for $4.6 million.


Bernard Kerik took an unorthodox path to become head of New York’s police department. A high school dropout and Army MP, he worked for and got fired from a security job in Saudi Arabia, ran the Passaic County jails in New Jersey, and joined the NYPD in 1986, doing undercover drug investigations, making detective and getting assigned to a Justice Department narcotics squad. But it was his relationship with Rudy that carried his career. The two tough-talking crime fighters and devout Catholics, who first met in 1989, cemented their bromance in 1993, when Giuliani was running for mayor and hired Bernie to be his driver. They hit it off. A year later, Rudy gave him the No. 2 job at the city’s Corrections Department, which Kerik took over in 1998. In 2000, Hizzoner made him police chief, the only time the department had a commissioner whose highest prior rank was third-grade detective. The two stood together following the 9/11 attacks, and shared the resulting adulation. But there was a dark side to Kerik, and many red flags. It turned out that he liked freebies. Kerik got $225,000 to renovate his Bronx apartment from a company doing business with the city. He took tens of thousands in bribes while serving as the jail’s boss. And in 2003, there was a $250,000 interest-free loan from an Israeli billionaire that he didn’t report, which the feds determined was a bribe. All told, Kerik pleaded guilty in 2010 to eight felony charges, including tax evasion, and was sentenced to four years in jail. At one point in 2006, he was briefly held at the Manhattan Detention Complex, which Giuliani had renamed Bernard B. Kerik Complex after his friend in 2001. It might have been the only time an inmate was locked up in jail with his name on the building.


For Giuliani’s foes, the blindside he had for Kerik was a gift that kept on giving. To be sure, president George W. Bush liked Bernie. In 2003, during Operation Iraqi Freedom, Bush appointed him interim Interior Minister of the country. Yet when the job of Homeland Security head became available in 2004, Rudy weighed in with the White House and “made a call,” according to Kerik, advocating strongly for his former chauffeur. Bush went along. Still, that a former federal prosecutor, New York mayor and security consultant at the highest level didn’t realize his close pal was on the take and had hired an undocumented worker as a nanny was hard for many to believe. The nanny issue forced Kerik to withdraw his nomination for Homeland, and the resulting scrutiny revealed Kerik’s corruption. Embarrassing the president isn’t the best way to endear oneself to the party in power, and Giuliani’s bid to get the GOP nomination — which many believed was a strong possibility — evaporated.

If you’d like to read more, we recommend this excellent piece by Jack Newfield in The Nation.

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