Harold Giuliani (1908–1981) was an Italian-American plumber and convicted felon best known as the father of Rudy Giuliani, the former Mayor of New York City and prominent political figure. Born into a working-class immigrant family in New York, he grew up in Brooklyn during the early 20th century, a time when organized crime was prevalent in Italian-American communities. His early life was marked by involvement in petty crime, reflecting the harsh economic conditions of the era. He married Helen Cermak in 1933, and they had two children, Rudy and a daughter named Helen. In 1934, Harold was convicted of armed robbery after holding up a milkman at gunpoint in Brooklyn, an incident that led to a sentence of up to 20 years in Sing Sing prison, though he served only a few years before parole. This conviction stemmed from his associations with local criminal elements, and post-release, he worked as a loan shark and enforcer for the mafia, collecting debts for figures connected to organized crime in New York. Despite his underworld ties, Harold maintained a facade of respectability through legitimate employment as a plumber, which provided a stable, if modest, income for his family. His criminal past was a closely guarded family secret during Rudy's formative years, only revealed later in life. Harold's experiences with the criminal justice system profoundly impacted Rudy Giuliani, who credited his father's stories and tough demeanor with instilling a strong sense of justice and anti-crime sentiment, influencing his son's early views on law and order. Harold retired in his later years and passed away in 1981 at age 73. His life exemplifies the complex interplay between immigrant aspirations, economic hardship, and the allure of organized crime in mid-20th-century America, leaving a lasting, albeit controversial, legacy through his son's public career.