Thug Life

The Shocking Secret History of Harold Giuliani, the Mayor’s Ex-Convict Dad

Sometime in the late '50s, Harold stopped tending bar full-time at Vincent's. On January 12, 1959, two and half months shy of his 51st birthday and shortly before Rudy's 15th, Harold Giuliani got his first on-the-books, legit job.He was hired for $3300 per year as a groundskeeper for Lynbrook Public High School in Lynbrook, Long Island, where Helen's younger brother Edward lived with his wife, Anna, and their three children.

Perhaps in connection with that job, Harold requested information about the cloud that had hung over him since 1934. A notation in the General Sessions court file indicates he sought copies of the "complaint and certification" of the criminal case against Joseph Starrett. The notation lists Giuliani at his Garden City address, indicating that copies of the key documents were sent to him there.

As a member of the buildings and grounds crew for the Lynbrook district, Harold spent his day maintaining sports equipment, buffing the terrazzo marble floors, grooming athletic fields, and, in the winter, salting parking lots and driveways.

Illustration by Tim Gabor

In October 1959, the Giulianis migrated once again. Harold, after only 10 months on the job at Lynbrook High School, took out a $162-per-month mortgage on a new, comparably capacious split-level ranch house in Bellmore, closer to Lynbrook. Fixed in a tidy row of similar houses on a short block called Pine Court, the Giulianis' new home, replete with a deck and a two-car garage, was Harold's castle.

Although open-minded and mild-mannered, Brother O'Leary was no softy when it came to discipline. When Rudy made a wisecrack in the middle of an afternoon lecture, his homeroom teacher marched over to the lisping upstart and cuffed him on the side of the head. In October 1959, the beginning of Rudy's junior year, at a Bishop Loughlin Memorial High School open house, O'Leary was surprised when Harold and Helen Giuliani tentatively approached him and thanked him for smacking their irreverent son. "They asked me if I remembered the time I punished Rudy. I said yes. They said, 'We want to thank you, because he became a much better student after that.' "

From that encounter, a relationship blossomed. Since Rudy and his friend Alan Placa were, in their earlier years, misbehaving to the detriment of other students, O'Leary "would report to my father on my conduct every week," Rudy said. This weekly check-in system soon evolved into a friendship with the Giuliani family. The young Catholic brother would join Rudy, his parents, and his grandmother for spaghetti dinners at their house in Bellmore.

The devoted Catholic brother would become one of the most important influences in Rudy's early life. "He was terrific," Rudy said. "He spent a lot of time with me, developing interests that I had that I wasn't comfortable about. Like reading and opera, things that I wouldn't talk to my friends about, because they would think I was a sissy."

Some evenings after dinner at the Giulianis', Harold, O'Leary, and Rudy would excuse themselves and take a stroll in a nearby park. They would discuss news, politics, matters of religion. Rudy might prattle on about Jack Kennedy or jaw with his father and teacher about the Yankees. Sometimes the high school senior would tread a few paces ahead or lag a few paces behind, and when he was out of earshot, Harold might broach other, more serious, matters with O'Leary. In the spring of 1960, during one of these walks, while Rudy tagged behind them, Harold made a sudden, cryptic confession to his confidant.

"I've done things in the past that I've paid for," Rudy's father said.

The men continued walking, wordlessly, the sounds of their feet on the path suddenly loud in the wake of Harold's comment. Keeping silent, O'Leary waited. He would let Harold offer an explanation, pour his heart out if needed. And O'Leary was ready for whatever this hard, vexed man had to tell him.

But Harold Giuliani said nothing more. As the dusk enclosed them, Harold shunted the conversation back to generalities, and Rudy caught up with them and the three sauntered together through the dark back to the house.

The following fall, Harold Giuliani REceived a letter from Richard P. McLean, the assistant superintendent of the Lynbrook Public Schools. Dated December 7, 1961, the letter read:

We have heard no word from you concerning your return to work in the Lynbrook Public Schools. The custodial staff is presently shorthanded one man. May I ask that we resolve this issue as soon as possible. . . . Your immediate response to this letter will be appreciated.

McLean was writing Harold because he hadn't been to work in months. Nearly two weeks after the first letter, the assistant superintendent sent the 53-year-old, AWOL custodian a second letter, terminating him.

Harold lost his job just as Rudy was finishing up his first semester at Manhattan College. Asked a few months earlier—in his February 1961 application for a scholarship from Italian American Charities—what he planned to do if financial assistance was not granted, Rudy had written: "My father will, of course, help to pay towards my college education as much as he can. Then I expect to work this summer. However, this will not be enough. I must, of necessity, have some outside aid in order to complete my education." He had listed his father's job as a custodian.

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