Growing Up Giuliani

On Sept. 16, 1992, the police in New York City held a rally that spun out of control. The cops wanted a new collective-bargaining agreement, and they were angry at Mayor David Dinkins for proposing a civilian review board and for refusing to issue patrolmen 9mm guns. More than a few of them tipsy or drunk, the cops jumped on cars near city hall and blocked traffic near the Brooklyn Bridge. According to some witnesses, they waved placards crudely mocking Mayor Dinkins, the first black mayor of New York, on racial grounds, while at the same time chanting "Rudy! Rudy! Rudy!" to welcome Rudy Giuliani, the crime-busting former U.S. attorney who had arrived in their midst to shore up his political base.

It is not clear Giuliani knew exactly what he was getting himself into—he later denied that he did—but video shows him wildly gesticulating and shouting a profanity-laced diatribe against Dinkins. The next day the New York newspapers were sharply critical of Giuliani (a Daily News editorial called his behavior "shameful"), and Dinkins, years later, accused him of trying to stir up "white cops to riot." At the time, Giuliani refused to back down or apologize for his remarks, saying only: "I had four uncles who were cops. So maybe I was more emotional than I usually am." Giuliani's performance that day lost African-American voters, some permanently, but it guaranteed the informal backing of the Patrolmen's Benevolent Association, the policemen's union, which helped him get elected mayor in 1993.

Giuliani has long had a soft spot for cops—even, in some cases, for bad ones. On the one hand, Giuliani has been a crusader against outlaw policemen, as well as mobsters, pornographers, drug dealers, crooked businessmen and politicians and death-dealing jihadists. He now offers himself as the presidential candidate who would deliver us from evil, from terrorism abroad and corruption at home. On the other hand, he was the man who appointed Bernard Kerik, now under indictment for various federal crimes, including tax evasion, to be his police commissioner, and later pushed him to become the nation's secretary of Homeland Security. (Persistently accused of ties to mobbed-up businessmen, Kerik has always protested his innocence of any criminal wrongdoing, but he pleaded guilty in the Bronx last year to ethics violations while serving as Giuliani's corrections commissioner.) Giuliani is a dramatic—and self-dramatizing—moralist. But as an intelligent, sensitive man with a solid Roman Catholic education, he knows there is sometimes a fine or blurry line between saint and sinner. He has been able to reconcile the rigidities of doctrine with the vagaries of human nature. He has long believed in the power of redemption, and he puts great faith in the virtue of loyalty. He does not shy from confrontation, but seems to welcome and even create conflict, especially if there are cameras nearby. His theatricality can be excessive, and not just because he has been known to dress up in drag as a spoof. Kerik has written that when he was welcomed into Giuliani's inner circle—in a clearly staged ceremony, with a kiss on the cheek from each member—he felt like a "made man." Leaving aside Kerik's unfortunate Mafia analogy, there is an intensity and intimacy to Giuliani that can be unsettling. He has an authoritarian streak, as well as a penchant for secrecy and dependence on loyalists, that may remind voters of the current chief executive.

The real Rudy is probably as complex and certainly as passionate as the operatic Rudy who shows up at cop rallies. He can be hero or hypocrite or both at once; he has a ripe sense of his own, and his nation's, magnificence and destiny roughly on par with that of Winston Churchill's, whose works Giuliani recommended to his schoolmates, along with his favorite operas by Verdi. Just as Churchill's character was shaped by the myths of his forebears in his ancestral home, Blenheim Palace, seat of the Duke of Marlborough, Giuliani's was forged by the moral ambiguities of his upbringing and the eternal American melodrama of rising above one's past while honoring, or at least accepting, it. Giuliani was born into an immigrant enclave—mostly Italian-American, some Jewish—in East Flatbush, Brooklyn, a neighborhood of looming dark churches and rows of modest brick and brownstone houses, far from the Manhattan skyline. Four of Giuliani's uncles were, indeed, policemen, as were four of his cousins. But another uncle was Leo D'Avanzo, a loan shark and a bookie with mob connections, who operated out of a bar named after another uncle—Vincent D'Avanzo, a policeman who acted as a frontman for the bar. Rudy's cousin, Leo's son Lewis (a.k.a. "Steve the Blond"), was a ruthless hood who later did time for armed hijacking and selling stolen cars.

The proximity of good and bad, even in Giuliani's own family, seems to have given rise to his inflexible public code but more relaxed personal one—a bifurcation that will only become more important in the next 10 weeks or so, as generally conservative Republican primary voters decide whether to trust this unconventional figure with their nomination. (When asked about the reporting in this story, Giuliani deputy communications director Maria Comella declined to comment.)

Working behind the bar at Vincent's for long stretches of time was Rudy's father, Harold. According to Wayne Barrett's biography "Rudy!," indispensable to all Giuliani profiles, Harold kept a revolver and a baseball bat with him in case the customers became too rowdy. Barrett writes that Harold Giuliani moonlighted as the "muscle" for his brother-in-law, using the bat and his fists to collect debts. A would-be boxer who was hampered by nearsightedness, Harold served more than a year in Sing Sing Prison for mugging the milkman.

Giuliani has said he did not learn about much of his father's past until he read about it in Barrett's book in 2000. As a boy—an only child—Giuliani was smothered with love and attention (and called "the Little Prince" by relatives). When Rudy was 7, Harold moved his family from Brooklyn to Garden City, a middle-class, virtually all-white suburb on Long Island. Harold later told one of Rudy's teachers that he wanted to get his son "away from some relatives that he didn't particularly care for, and so Rudy could have a solid bringing up without any temptations to break the law." Though in 1951 East Flatbush was still relatively untouched by the great postwar migration of Southern blacks to Northern cities, white flight had begun in Brooklyn. Tony Mauro, a college classmate of Giuliani's who lived in nearby Crown Heights and whose family moved to Garden City in 1950, recalls his father's accounts of real-estate agents' scaring residents by warning of diminishing property values and crime.

Middle-class Catholic families sent their children to parochial schools if they could. Public school, as depicted in a popular 1955 movie, "The Blackboard Jungle," was a place where pupils had their lunch money stolen—or worse. At Catholic schools, students wore uniforms and stood when teachers entered the room, and they received daily religious instruction. Rudy won tuition-free admission to Bishop Loughlin Memorial, a fortresslike high school run with an iron hand by the Christian Brothers. When some students played the Everly Brothers' "Wake Up Little Susie" at a school dance, one of the brothers smashed the record over his knee and announced, "We'll have none of that filth playing here."

Sophomore year, Giuliani's homeroom teacher was a Christian Brother named Jack O'Leary. Giuliani was more of a talker than a scholar. "I hit him once," O'Leary tells NEWSWEEK. "He was talking in class, and unfortunately—the custom of the time, if someone was fooling around you gave him a whack—and that's what I did." Giuliani quieted down. About a year later, in the school auditorium, O'Leary ran into Giuliani's parents, who introduced themselves. "They said, 'Do you remember the time you hit him?' And I said, 'Yes I do'," O'Leary replied. "And they said, 'We want to thank you because it made all the difference'." Sports teams were revered at Bishop Loughlin. Pudgy and not particularly athletic, Giuliani had to look for other outlets. With O'Leary, he formed an opera club. While other teens were jitterbugging and slow-dancing to the Everly Brothers, or trying to, Giuliani was listening to Verdi's "Otello," immersing himself in the beauty of Italian high-culture tragedy and romance.

He was also learning how to be a pol. John F. Kennedy ran for president in the fall of 1960, Giuliani's senior year, and Giuliani was thrilled and moved by the handsome and eloquent young man who was rising above old prejudices to become the first Catholic in the White House. Giuliani persuaded some other boys to skip school and go to a Kennedy rally in Manhattan. ("I saw him! I saw him!" he said to O'Leary when he returned to class.) Giuliani managed a friend's campaign that year, hiring a U-Haul with a loudspeaker to cruise outside the school, but his highest office was hall monitor. He seemed to enjoy wearing a badge and disciplining students for minor infractions, such as talking during a fire drill. "He had a stern look," says Jack J. Rengstl, another former Loughlin student. In the yearbook, in the usual "Most likely to …" categories, he was voted "Class Politician."

Giuliani was jovial and thick-skinned, says George Schneider, the boy for whom Giuliani served as campaign manager ("He volunteered," says Schneider). "Rudy was slouching in a chair and had his foot in the aisle," recalls Schneider. "The teacher said, 'Hey, fat boy, get your foot out of the aisle.' Everyone laughed, including Rudy. He was unfazed. Then the teacher came down [the aisle] and cuffed him in the head." Giuliani "couldn't figure out what he had done," Schneider says, and seemed a bit stunned.

Corporal punishment was routine at Bishop Loughlin. Adolescent anarchy was a fearful thing; the Brothers beat it out of kids. Some students were afraid. "When you see someone picked up by the shirt and tie and punched in the face, or other teachers throwing chalk across the room—it was very scary," says Joseph Sicinski, who was Giuliani's classmate.

At Bishop Loughlin, Giuliani was a catechist, a student who instructed younger children in Catholic doctrine. Giuliani was not remarkably pious, but like many dutiful boys of his time and background, he seriously considered the priesthood. (He would later joke to friends that he gave up his priestly ambitions because "celibacy ain't for me.") But Giuliani wound up applying for a college scholarship "to study law or medicine," the classic roads of upward mobility for the sons of immigrant families.

O'Leary, who had grown close to the Giulianis and often dined with them, recalls that Giuliani gave up the seminary for another, more personal, reason. Near the end of Giuliani's senior year, his father had a nervous breakdown. At a state park on Long Island, a policeman walked into a men's bathroom to find Harold Giuliani, with his pants down around his ankles, doing deep knee bends. Harold was arrested for loitering. It was all an embarrassing mix-up. He had been constipated and he was trying to expedite a bowel movement. Harold also stopped showing up at his job as a school custodian. O'Leary says Giuliani felt he could not leave his family for the enforced isolation of the seminary.

Always, the Manhattan skyline shimmered. After high school, Giuliani joined the flood of Long Island commuters into Gotham, to Penn Station, where he transferred to the uptown subway to the distant Bronx. There he was enrolled at Manhattan College, another strict and demanding institution for strivers run by the Christian Brothers. Of the 744 students in his class, three were black and four were Hispanic. Blackballed by the fraternity favored by jocks and campus "big men," Giuliani joined a smaller frat he helped revive. It soon had 30 members. He honed his political skills (this time he had campaign buttons made) and was elected class president.

Under the Christian Brothers' tutelage, Giuliani was exposed to the Christian Aristotelianism of Saint Thomas Aquinas. As writer John Judis recently noted in The New Republic, "Catholic thinkers do not see liberty as an end in itself, but as a means—a 'natural endowment'—by which to achieve the common good." Many years later, at a forum on crime, Giuliani said, "Freedom is about authority. Freedom is about the willingness of every human being to cede to lawful authority a great deal of discretion about what you do." Asked to explain what he meant, Giuliani replied, "Authority protects freedom. Freedom can become anarchy." Judis notes that Norm Siegel, then executive director of the New York Civil Liberties Union, said afterward that he was "floored" by Giuliani's definition of liberty and authority. "But anyone who studied philosophy at a Catholic college would not have been surprised by Giuliani's words," writes Judis.

Giuliani's politics in the 1960s were fairly liberal. He was influenced by Robert Kennedy, but perhaps more by RFK's law-and-order side and penchant for power than his leanings on civil rights. Though Giuliani was in college and law school during the tumultuous student revolutions of the '60s, he was untouched by flower children, and he avoided antiwar rallies. He didn't want to get arrested and jeopardize his emerging ambition: to become a prosecutor.

It's unlikely that the young Giuliani wanted to become an Inspector Javert, the sort of I-am-the-law type of prosecutor who righteously condemns wrongdoers. Giuliani was sophisticated enough to have read Victor Hugo, and his colleagues say he was fair-minded, if zealous and extremely hardworking as a young lawyer. But it is a sure bet that Giuliani wanted the thrill of standing up for the "people" in court or signing his name on a legal brief "for the United States of America."

The best way to compete against the Ivy League hotshots vying for the position of assistant U.S. attorney was to clerk first for a federal judge. Giuliani was hired by Lloyd MacMahon, known as a cranky coot who favored working-class go-getters from second- and third-tier law schools. Addressing lawyers in his courtroom as "morons" and "boobs," Judge MacMahon was not bashful on the bench. "Call your next liar," he once growled at a defense lawyer. His arbitrariness and high-handedness got him reversed so often in the court of appeals that he was pronounced one of the nation's "worst judges" in an American Lawyer magazine survey. But MacMahon fearlessly put away mobsters and communists, and he was a good mentor to Giuliani. When Giuliani's draft deferment ran out in 1969, the judge intervened personally to get his clerk another deferment. (Giuliani had dropped out of Air Force ROTC, citing a slight hearing impediment, and told colleagues that Vietnam did not meet the Catholic definition of a "just war.") Then MacMahon helped get Giuliani his dream job as an "AUSA," a junior prosecutor in the most prestigious of all U.S. attorney's offices, the Southern District of New York—Manhattan.

In the early '70s New York City was in the midst of its worst police scandal in decades. The Knapp Commission, appointed by Mayor John Lindsay, had unearthed scores of cops on the take, accepting bribes and selling drugs, sometimes stealing cash off corpses. In 1972 the French Connection case broke—somehow, nearly 400 pounds of heroin had vanished from the police property clerk's room. Giuliani's involvement in the case is revealing of his character as shaped by his family roots.

Giuliani was working with a dirty cop who had turned informant. Having grown up in a household of cops, Giuliani was comfortable with New York's Finest, even when they weren't. Unlike FBI agents, who could be cautious and bureaucratic, New York City police officers were willing to take risks. If that meant bending the rules to meet the necessities of the street, then so be it.

Bob Leuci had done more than bend the rules. As a member of an elite group of 60 detectives known as the Special Investigative Unit (SIU), Leuci had taken money from dope dealers, done some illegal wiretapping and routinely paid informants with seized drugs. In the midst of the Knapp Commission probe, "Babyface," as he was called, decided to cooperate with the Feds, wearing a wire as he went undercover to meet with corrupt law-enforcement officials and lawyers. The French Connection case had broken, and prosecutors suspected that Leuci knew more than he was telling. It was up to Giuliani to get him to talk.

By befriending Leuci and winning his trust, by swearing never to abandon him, Giuliani succeeded. Leuci had not been involved in the French Connection case, but he was able to finger a new slew of "bad guys." Tom Puccio, the U.S. attorney in Brooklyn, would later say that he and Giuliani had played "bad cop/good cop" with Leuci, but Giuliani seemingly refused to look cynically at his role. He knew that a judge had once called SIU detectives "princes of the city," and to Giuliani, Leuci was still a prince—albeit a fallen one. Giuliani, Leuci said, believed in redemption.

Giuliani understood that it was "something like penance in the Roman Catholic Church—it was part of that 'I did something bad, now I need to do something good'," Leuci tells NEWSWEEK. "Rudy recognized that whole Catholic guilt stuff. I think he was smart enough to know he could play to it." Leuci was suicidal at the time and he later said that if Giuliani had pushed too hard, he would have killed himself. Instead, Giuliani befriended Leuci, talking about family, about how much he honored his father. It has never been entirely clear how much Giuliani knew about the shady past of his dad and other family members, but Giuliani was able to convey empathy and understanding about moral ambiguity. At the same time, Leuci says, "I wouldn't want Rudy as an enemy, I'll tell you that. He's not a guy that rests."

Loyalty has always been the greatest virtue to Giuliani, sometimes trumping all others. By loyalty, Giuliani's critics contend, he means "loyalty to Rudy." Disloyal subordinates learned this the hard way, even if they thought they were serving some higher master, like truth and justice. By the early '80s Giuliani had risen to claim a top job in the Reagan administration Justice Department. At the time the department was investigating McDonnell Douglas, the aircraft manufacturer, for making foreign bribes. Without telling career prosecutors who had been working on the case for months, Giuliani met with McDonnell Douglas defense lawyers. The career prosecutors were upset that a top official had gone over their heads, and wrote a letter to Giuliani expressing "shock" and "dismay" and warning that his secret meeting with the defense could undermine the prosecution's case. The letter leaked. Giuliani summoned the prosecutors, Michael Lubin and George Mendelson, to his office—and exploded.

"As far as I'm concerned, we were watching a madman," Lubin told Jim Stewart for his book "The Prosecutors." "I've never heard or seen anything like it, even in the movies. He ranted and raved for a full twenty minutes." Giuliani, who later dropped criminal indictments against four McDonnell Douglas executives as part of a plea agreement in which the company paid $1.2 million in fines, dismissed Lubin and Mendelson as "jerks." With petty vindictiveness, he withdrew a special Justice Department commendation awarded the two prosecutors. (A later internal Justice review found no wrongdoing on Giuliani's part.)

Giuliani's critics have long complained that Giuliani surrounds himself with yes men, or "Yes Rudys," as they are called. Loyalty is not always a two-way street for Giuliani, either in his family or professional life. Giuliani's fraught relationship with former New York senator Alfonse D'Amato is a case in point.

In 1982, Associate Attorney General Giuliani traveled to Miami to handle a complex case concerning the legal status of boatloads of Haitian refuges. While he was in Miami he met a TV newscaster named Donna Hanover. Giuliani's first marriage was effectively over by then—Giuliani had married Regina Peruggi, his second cousin, in 1968, but they were bound for divorce. He was smitten by Hanover, who was as vivacious as Giuliani, and he wanted to follow her to New York, where she was looking for a TV job. But Giuliani's Justice job kept him in Washington, D.C.

D'Amato tells NEWSWEEK that Giuliani went to the New York senator to ask a big favor: would D'Amato nominate Giuliani to be U.S. attorney in New York? D'Amato was in an awkward position: the job is a plum, and a committee of top lawyers had already put forth another candidate. Still, D'Amato was impressed with Giuliani, and he felt a bond as a fellow Italian-American. He gave Giuliani the nod.

At first the two men were fast friends. They garnered headlines (and a certain amount of mockery) by donning shades and traveling to Harlem to make a buy-bust. The publicity stunt was supposed to show how seriously the government took the war on drugs. It certainly suggested a budding political alliance.

But the relationship soured. In 1988 Giuliani began preparing to step down as U.S. attorney for a possible run against incumbent Sen. Daniel Patrick Moynihan. By then D'Amato was under an ethics cloud. As a member of the Senate Banking Committee, D'Amato had close ties to the securities industry. Giuliani had made a big show as the scourge of Wall Street, arresting analysts and brokers suspected of stock fraud and forcing them to take "perp walks" before the cameras. Giuliani said it would be irresponsible for him not to be concerned about the selection process, given the ongoing investigations into D'Amato's friends in the securities industry. Meanwhile, Giuliani was maneuvering to put one of his own deputies into the job and gossiping to reporters about D'Amato's alleged ethics problems.

D'Amato "went through the roof," says a former aide, who requested anonymity to describe the details of the D'Amato-Giuliani relationship. To his aides he began shouting profanities about Giuliani. ("I'm going to kill the f–––ing c–––––––er!" he said, the aide tells NEWSWEEK.) To his partisans Giuliani had not double-crossed D'Amato but rather showed moral rectitude by distancing himself from a crony of Wall Street inside-traders. During the 1989 mayoral primary D'Amato called his selection of Giuliani "the biggest mistake I ever made" and described his former protégé as an "amoral" political opportunist. The blood feud continued: when D'Amato ally George Pataki ran for governor of New York in 1994, Giuliani endorsed liberal Democrat Mario Cuomo. Giuliani explained that "ethics will be trashed if the D'Amato-Pataki crew ever get control." Contacted by NEWSWEEK last week, D'Amato said he no longer wanted to talk about his old feud, but he is throwing fund-raisers for Fred Thompson and coaching him on how to debate Giuliani.

Loyalty to Giuliani means staying out of his limelight. Police Commissioner William Bratton discovered that in January 1996, when he made the mistake of posing for the cover of Time magazine in a trench coat to tout New York's astonishing success at fighting crime. Giuliani was not pleased; he ordered city hall's lawyers to start investigating Bratton's expenses, and the commissioner was gone in a couple of months. (Giuliani disputed that he or his staff undermined Bratton but noted that they "both had very, very strong styles.") In truth, both men deserve credit for New York's turnaround. Bratton was a vocal apostle of the "broken window" theory of crime—that small acts of vandalism can create a lawless climate conducive to bigger crimes. But Giuliani, the product of 16 years of Catholic schools where neatness and order were measures of moral health, instinctively understood that small sins can lead to big ones. Not long after his swearing-in as New York's mayor in January 1994, Giuliani launched a no-tolerance campaign against the "squeegee men," small-time shakedown artists who would ask for payment for wiping the windows of the cars of terrified tourists and suburbanites as they waited at red lights.

Giuliani never found an equal to Bratton. The next commissioner, Howard Safir, was regarded as a "Yes Rudy" who tried too hard to please his master. ("I am very loyal to Rudy," Safir tells NEWSWEEK. "However, when I disagreed with him … I made sure I did it in private.") The police stepped up their stop-and-frisk campaign in poor, largely minority neighborhoods. A series of ugly police-brutality cases besmirched Giuliani's crimefighting record and alienated blacks and Hispanics. In 2000, when an undercover narcotics detective killed an unarmed security guard named Patrick Dorismond, who was black, Giuliani scoffed that Dorismond was no "altar boy." Actually, he was an altar boy—and had attended Bishop Loughlin high school.

Giuliani's loyalty to his last police commissioner, Bernard Kerik, bordered on the blind. The two men had come to know each other when Kerik, acting as an off-duty cop, drove Giuliani during his first mayoral campaign in 1989 (Giuliani lost to Dinkins). Kerik was the sort of diamond in the rough Giuliani appreciated—a tough street cop who got things done. Giuliani has insisted that he did not know about Kerik's questionable dealings with two businessmen with alleged mob connections. City hall records reviewed by NEWSWEEK suggest that the mayor may have been briefed on some of these problems just before Kerik was appointed commissioner. But Giuliani has said he has no memory, and his tight palace guard remains closemouthed. ("There were mistakes made with Bernie Kerik," Giuliani said earlier this month, adding that Kerik's wrongdoing should not outweigh his crimefighting successes.)

Giuliani's moralism became increasingly strident in his second term as mayor. He was outraged at an art show at the Brooklyn Museum called "Sensation." The exhibits included a picture of a black Virgin Mary surrounded by bits of pornography and a pile of elephant dung. Giuliani ordered the museum to shut down the show or lose its city subsidy. He lost in the courts; the show went on. Yet he has stood by his boyhood friend, Msgr. Alan Placa, who was accused of, though never formally charged with, child molestation. (He denies the allegation.) The boy who had grown up with cops and hoods in his family was able to maintain a somewhat selective sense of right and wrong—one influenced by tribal ties.

While Giuliani was ranting at moral decay, his personal life was a shambles. In Giuliani's last year in office, Donna Hanover learned that her husband was divorcing her when he gave a press conference. Giuliani's third wife, Judith Nathan, has provided fodder for the tabloids by wearing a tiara to a charity ball and seeming to enjoy Giuliani's perks and power a little too much.

It may be, however, that Giuliani has finally found his true soulmate, someone who shares his aspirations for power and glory. Giuliani himself can seem overly anxious to make money from his reputation as America's Mayor on 9/11. He earned $11.4 million in speaking fees between January 2006 and May of this year, as well as an additional $1.2 million in the same period from his law firm, Bracewell and Giuliani. He also took in $4.1 million from Giuliani & Co., the corporate umbrella for an array of consulting firms that have provided advice to foreign and domestic clients under arrangements that often remain secret. Giuliani's law firm also represents a long list of lobbying clients in D.C., including energy, petrochemical and defense firms. Giuliani himself hasn't registered to lobby, and doesn't believe his law-firm clients are a political liability. "Law firms aren't political, so this is kind of a silly way in which people attack each other on politics," he told reporters last July, responding to controversy over one of his firm's legal clients, an oil company owned by the government of Hugo Chávez, the virulently anti-American Venezuelan president. (The firm has since dropped that client.)

Giuliani didn't grow up with wealth or power. He can't take it for granted, as can the current president or one of Giuliani's leading rivals for the GOP nomination, Mitt Romney. Yet his struggle to get to the top may have left him with a chip on his shoulder: he's had to fight for what he's achieved, so what he's got he deserves. Giuliani's upbringing has also given him an appreciation for the darker elements of the soul, and the strength required to keep them in check. He can be tolerant, particularly of his own failings or of those who are loyal to him. But don't cross him. In Rudy's world, that is one sin that cannot be forgiven.

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