MR. CARBONETTI GREW up on 116th Street and Second Avenue in what was then called Italian Harlem.
His grandfather, Louis Carbonetti Sr, was a Democratic district leader and antagonist of the infamous Tammany Hall’s Carmine De Sapio. Louis was also pals with a failed stickup artist named Harold Giuliani.
Their sons, Louis Carbonetti Jr. and Rudy Giuliani, also became friends.
As Mr. Giuliani built a successful career as a prosecutor, Mr. Carbonetti’s father stayed in East Harlem, established a printing company and eventually raising three sons with his wife, JoAnna Aniello, a city worker.
A political junkie like his father and childhood friend, Louis took his middle son, Tony, to the 1976 Democratic convention at Madison Square Garden.
“I still have some of the buttons that we bought then,” said Mr. Carbonetti. “My dad just sent me some of the ‘Romney for President’ buttons from 1968. It’s just amazing how much Mitt looks like his dad.”
A year later, the Carbonettis moved to the mostly uninhabited Queens neighborhood of Roosevelt Island. When his parents split, the 13-year-old chose to stay with his father. His two brothers, Louis, now a printer in North Carolina, and Joseph, now the owner of a pub called the Brass Monkey on 12th Street, went to live with their mother in Brooklyn. (Mr. Carbonetti has a third brother through his father’s second marriage.)
Just a few years later, in 1986, Mr. Carbonetti, an A-average high school student at the La Salle Academy on Second Street, went to get career advice from then U.S. Attorney Rudy Giuliani, who former Parks Commissioner Henry Stern called “a surrogate father to him.”
“‘Become a lawyer,’” Mr. Carbonetti remembers Mr. Giuliani telling him. “Everyone wanted me to be a lawyer. I never listened.”
Boston University didn’t suit Mr. Carbonetti. He said he found his political science major too abstract and unsatisfying. He was restless. So when Mr. Giuliani ran for mayor in 1989, Mr. Carbonetti took a semester off to perform menial tasks on the campaign.
Mr. Giuliani lost to David Dinkins, and Mr. Carbonetti went back to school. When his father’s business went bankrupt in 1990, he ran out of money for tuition. He attended graduation but never received a diploma. The bar he tended to was called Cityside in Boston’s Faneuil Hall.
In 1992, with Mr. Giuliani about to make another run for mayor, Mr. Carbonetti contacted Peter Powers, then Mr. Giuliani’s chief adviser, to offer his services. A few weeks later Mr. Carbonetti was made a deputy director of field operations.
“He was a natural magnet for field workers and really motivated them,” said Mr. Mastro, a former deputy mayor for Mr. Giuliani and fellow member of Mr. Giuliani’s inner circle who played a key role in the 1993 campaign. “You had to sort of create the field operation from the ground up. He was instrumental in building that organization.”
This time Mr. Giuliani won, and Mr. Carbonetti, a 24-year-old registered Democrat who reporters joked had only the qualification “mixologist” to put on his résumé, became “director of appointments,” a post from which he gave out jobs, or more accurately, cleansed the city agencies of any trace of Mr. Dinkins’ influence.
(Mr. Carbonetti’s father also received an administration post, but was forced to resign in 1995 as the result of a financial scandal. His mother received a promotion to a lucrative position at the city’s Housing Authority as Mr. Giuliani prepared to leave office.)
His only prior work experience before his fortuitous City Hall appointment by Mr. Giuliani was as a bartender in Boston.