It’s not a simple case of "like father, like son" when it comes to Rudy Giuliani.
Rudy’s father, Harold Giuliani, spent time in Sing Sing for armed robbery. In contrast, as U.S. Attorney for the Southern District of New York, appointed by President Reagan, Rudolph Giuliani targeted and prosecuted the heads of New York’s five mob families — Paul Castellano, head of the Gambino crime family; Carmine Persico, head of the Colombo crime family; Tony Corallo, head of the Lucchese crime family; Philip Rastelli, head of the Bonanno crime family; and Tony Salerno, head of the Genovese crime family.
Selecting Rudy Giuliani as its Person of the Year for 2001, Time magazine included the following information on Giuliani’s father in its "Mayor of the World" profile: "By conventional standards, Harold Giuliani was not a great man. In 1934, he was arrested for robbing a milkman at gunpoint in the vestibule of a Manhattan apartment building. A court-appointed psychiatrist diagnosed him as an ‘aggressive, egocentric type.’ He served a year and a half, and then went to work as a bartender and enforcer for his brother-in-law Leo D’Avanzo’s loan-sharking operation, according to court documents and eyewitness accounts uncovered by Giuliani biographer Wayne Barrett."
As the case against the top bosses of the New York Mafia began, Rudy Giuliani explained his strategy and objective in simple terms: "Our approach is to wipe out the Five Families." In equally simple terms, he described his overall mission: "To make the justice system a reality for the criminal."
The "reality" in this case turned out to be hundreds of years in prison terms for eight top-level New York mob bosses. Prior to leaving the courthouse and never to see freedom again, Corallo offered the traditional "Cent’Anni" toast, "May we live 100 years." Replied Lucchese family underboss Salvatore Santoro, "I think it’s time to get a new toast."
Arguing that it’s a mistake to "socialize the responsibility for crime," a mistake to turn the explanations for crime into excuses for crime, Giuliani stresses individual accountability rather than collective culpability: "We elevate human beings by holding them responsible. Ultimately, you diminish human individuality and importance when you say, ‘Oh, well, you’re not really responsible for what you did. Your parents are responsible for it, or your neighborhood is responsible for it, or society is responsible for it.’ In fact, if you harm another human being, you’re responsible for it."
Said another way, Giuliani didn’t use his neighborhood or his mob-connected in-laws or his father’s criminal past as an excuse for failure.
In 1993, he became the first Republican in a generation to be elected mayor of New York City. In 1997, in a city where Democrats hold a five-to-one registration advantage over Republicans, Giuliani was re-elected with nearly 60% of the vote.
By the time his eight years were completed, overall crime in the city (rapes, assaults, burglaries and car thefts) was down by 64%, the murder rate was reduced by 67%, taxes were cut by 20%, the squeegee men (windshield cleaners who coerced drivers into giving them money at traffic lights) were out of business, the city’s economy was growing faster than the nation’s for the first time since World War II, Times Square was no longer a porno district, tourism had increased by 50%, the city’s payroll was cut by 20,000 jobs without layoffs, construction permits had increased by 60%, the mob was gone from the Fulton Fish Market, the city’s unemployment rate had dropped from 10.3 to 5.1%, 640,000 fewer people in the city were collecting welfare, and an inherited $2.2 billion budget deficit was turned into a multibillion dollar surplus.
Prior to Giuliani’s election, between 1990 and 1993, taxes in New York City had been raised by $1.5 billion and the city had lost 340,000 jobs — 192,000 in 1991 alone, the largest annual job loss ever experienced in an American city.
To reverse the downward spiral, Giuliani eliminated or reduced 23 taxes, saving individuals and businesses a record $8.1 billion. The result was a record 450,000 new jobs created in the city’s private sector within seven years and a 55% increase in overall personal income. "Tax reductions spur growth," explained Giuliani.
All told, not a bad step up from Sing Sing in one generation.