Pledging Allegiance

Helen D'Avanzo Giuliani's side of the family included men with links to organized crime. Rudy's troubled cousin, Lewis D'Avanzo, had grown up in Brooklyn, not far from where Harold Giuliani had lived and worked for Lewis's father, Leo D'Avanzo, a Mafia-connected bar owner who was a bookie and a loan shark on the side. Harold tended the bar and sometimes collected debts. Having considered a career as a boxer, he was good with his fists, an ideal enforcer.

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It was not Harold's introduction to trouble. In the early 1930s, a decade before Rudy was born, he robbed a New York milkman, a crime for which he spent about a year in Sing Sing prison -- another episode in Harold's life that his son would later say he knew nothing about until he read Wayne Barrett's 2000 biography, "Rudy!"

Long after Harold's release from prison, his associations with some of his Brooklyn in-laws meant that trouble continued to lurk. But, after his enforcer-bartender period, Harold decided to change his life and get his young son away from the influence of criminal family members, O'Leary says.

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Harold rebuilt his life on Long Island, eventually landing a full-time job during Rudy's teenage years as a custodian and groundskeeper at a public high school. He bought a house in a working-class neighborhood of North Bellmore, where homes generally went for about $20,000. The couple who lived across the street, Ray and Carole Jacobelli, admired Harold as a good neighbor and a devoted family man intent on guiding his son. "In every conversation I ever had with Harold, it was always 'Rudy, Rudy, Rudy,' " Ray Jacobelli says.

Rudy won a scholarship to Bishop Loughlin Memorial High School in Brooklyn, where the student body was made up of Catholic children of Italian, Irish, German and Polish immigrants -- all of whom attended tuition-free, and the smartest of whom, like Giuliani, had been tapped from parish elementary schools in a competitive process. Giuliani rode a train and the subway for an hour each morning to get to the school, where, during sophomore year, he took his place in Room 411.

He sat in the front row, with a tan crucifix hanging directly in front of his eyes, and talked and talked. His gabbiness during homeroom irked his teacher, Jack O'Leary, known then as Brother Kevin. After several warnings, O'Leary says, he slapped Giuliani across the head. "He didn't really say anything after I did it," O'Leary remembers. "He just gathered himself and became quiet and moved on to his work. He was good after that."

The next fall, at a parents' open house, Harold and Helen Giuliani thanked O'Leary for what he'd done, noting that Rudy's grades had improved markedly after the slap. Harold invited him to dinner at the Giuliani home, the first of several Sunday dinners there for O'Leary over the next two years. "I think Harold was pulling me into their circle for Rudy's sake," O'Leary says. "I think he was sending a message to his son: 'Here's a member of a religious order. Do it his way.' Not that he necessarily wanted Rudy to go into a vocation, but he wanted him to live the right way. . . . I guess Harold saw me as kind of a confessor."

Eventually, Harold told O'Leary that he had made a serious mistake many years earlier and that he had paid for it. "I knew in context what Harold was saying," O'Leary recalls. "He'd committed a crime and gone to jail for it. He was proud he'd rebuilt his life."

Harold had found a measure of redemption by protecting Rudy from a dysfunctional family dynamic that he feared might threaten his son's well-being. But in the midst of Harold's emotional breakdown, it was his son's turn to be protective. Standing resolutely by his father, Rudy Giuliani went off as a commuting student to suburban Manhattan College and returned in the evenings to North Bellmore to be with his parents. He kept his father's problems a secret from one of his closest friends, Peter Powers, a Bishop Loughlin classmate who went on to Manhattan with him and would one day run Giuliani's mayoral campaigns and become his first deputy mayor. "I never knew about it at the time," Powers said of Harold Giuliani's arrest. "I don't think I would have mentioned something like that to a friend, either."

Then, as now, Powers and Giuliani were "like brothers separated at birth," Powers says. Their circle included another bright, ambitious Bishop Loughlin classmate, Alan Placa, who sometimes double-dated with Giuliani. Placa pledged the same fraternity at Manhattan as Giuliani and Powers did, and became editor in chief of the student newspaper. Giuliani was a liberal columnist for the paper and a passionate fan of John F. Kennedy.

The three friends would go on to New York University Law School, after which Placa would become a Catholic priest. The men's devotion to one another has remained absolute in the four decades since. Placa helped Giuliani secure a church annulment of his first marriage, officiated at his second marriage, baptized both of his children and presided over the funeral of Giuliani's mother in 2002. During his mayoral years, Giuliani invited Placa to join his staff at Gracie Mansion, but Placa declined.