Thug Life

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

Behind the mahogany bar at Vincent's Restaurant, puffing on a cigar while he drew pints and fixed cocktails, was Harold Giuliani. The 40-year-old father of a four-year-old son had a patchwork employment history of a few on-again, off-again jobs. Nearly two years after prison, in July 1937, at the age of 29, Harold had applied for a Social Security number, listing his job status as "unemployed." At some point in the late '30s or early '40s, he tried his hand at door-to-door salesmanship, hawking tablecloths and bedspreads, before going on to work briefly at the Navy Yard. Now what Harold needed most was security and a weekly paycheck. The one man who could provide both was his brother-in-law, whose illegal operations were fronted by his other brother-in-law, the cop. "My father-in-law [Leo] was kind of close with Harold," noted Lois D'Avanzo, who would later marry Leo's son Lewis.

Like his brothers-in-law, Harold was a snappy dresser, usually attired in a starched shirt and tie and wearing a hat. Relatives described him as an affectionate man, who hugged as tight as a vise and kissed old ladies and children. Because of his stomach ulcers, the gray-eyed, bespectacled bartender often drank milk while his customers knocked back scotch. In case anyone got too rowdy, he kept a baseball bat behind the bar and a .38 caliber pistol next to the cash register. An opinionated and voluble Yankees fan in Dodgers-land, a man who reputedly hated most politicians, Harold would engage in heated arguments with his customers, his voice booming sometimes out into the street. If there was a bar fight, it was Harold who broke it up. If a customer had let his tab go for too long, it was Harold who went with his baseball bat to collect.

But bar tabs weren't the only debts Harold collected. He had come a long way since the spring day more than 14 years ago when he mugged a milkman. Now the crimes he committed were part of an organized criminal enterprise. Known as the "muscle" behind the loan-sharking operation, Harold was Leo's collection agent, recouping money that had been loaned out and was now overdue.

Illustration by Tim Gabor

Most debtors would pay at the bar, slipping an envelope to Harold across the counter. In the mid to late '50s, Harold collected as much as $15,000 a week, tapping dozens of debtors. The "vig" usually began at a stifling 150 percent and rose with the passing of each week. Many people borrowed money to pay rent or foot a business expense and would pay back four or five times the amount they borrowed. There were no excuses for being late.

One afternoon, a man reluctantly entered the bar to apologize to Harold, saying that he didn't have the money—could he have just one more week? Frowning, Harold reached under the bar, out of sight, and gripped his baseball bat. As the man before him continued pleading for an extension, Harold swung the bat, cracking him flat across the face, sending him back a few feet. "Don't be late again," Harold said, according to an eyewitness.

That was the gist of Harold's job: enforce Leo's law through threats or violence. He shoved people against walls, broke legs, smashed kneecaps, crunched noses. He gave nearby Kings County Hospital a lot of business.

"People in the neighborhood were terrified of him," said a frequent customer at Vincent's, who was one of Leo's son Lewis's best friends and whose family borrowed money from Leo.*

He remembers what happened early one Saturday morning after his own father failed to make a payment. "When I was a kid, my father borrowed money from Leo," he said. "He couldn't pay, so Harold came to collect. He knocked on the door and yelled, 'I want the money now, or I'm going to break both your arms!' "

After Harold calmed down, an agreement was worked out. "They talked to Leo and straightened it out," he said.

While in high school, Lewis's friend did occasional chores around the bar, and his brother took a job in the wire room, charting bets on the numbers boards. Many years later, after opening his own business, Lewis's friend borrowed $90,000 from Leo and paid back $160,000, a fairly modest repayment total. "It would only take me four to five weeks to pay him back," he said, adding that his brother once borrowed $5000 and ended up paying back $20,000.

Gambling, loan-sharking, and booze weren't the only sources of income at Vincent's. A black man who worked in the payroll office at a local hospital would stop by the bar every week or so to give Harold several dozen fake paychecks. The checks were made out to a host of fictitious employees and were drawn on the hospital's bank account. "Harold would cash them in the bar," said Lewis's friend. "There would be several thousand dollars' worth of checks every week. Harold would get half, and the black guy would get the other half."


Harold told his confidant, Jack O'Leary, A Christian Brother who was one of Rudy's teachers, that one reason he left Brooklyn in 1951, moving to Garden City, Long Island, was "to get away from my in-laws." He didn't want his son exposed to what went on at the bar, he explained, and vowed that his boy would not end up like Lewis, Leo's boy, who hung around the numbers charts and lived with his family in the apartment above the new bar.

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