Born on March 31, 1944, in South Brooklyn, New York, Bartholomew “Bobby” Boriello grew up in a lens into organized crime, surrounded by major Mafia families—Gambino, Genovese, and Colombo. His younger brother, Stevie, was tight with the Gallo brothers—“Crazy Joe,” Albert, and Frank Illiano—who were big-time players in local rackets. After Crazy Joe’s murder, Stevie helped hold down their South Brooklyn operations. At a towering 6'3", Bobby became a feared enforcer not just for the Gallo outfit, but eventually for the Gambino family.

In the late 1960s, Bobby found himself arrested six times—in charges ranging from weapons possession to assault and gambling. This string of arrests reflected his deep involvement in organized crime activity even before he fully “made” it in the Mafia world. By the 1980s, Boriello had officially become a made man in the Gambino family. He developed a tight bond with John Gotti, acting as his bodyguard and chauffeur, and earned trust among other heavyweights like Salvatore “Sammy the Bull” Gravano and the Corozzo brothers. When Gotti partied, Boriello rode shot-gun—often accompanying him on weekends filled with gambling and performances by childhood friend Jay Black.

As Gotti's favored bodyguard and chauffeur, Boriello was deeply trusted. He wasn’t just muscle—he was key to enforcing the Gotti regime, handling street-level operations and acting as a liaison for various illicit ventures around Brooklyn. His crew extended from Manhattan to Queens, Staten Island, and especially South Brooklyn, where he oversaw rackets including loan sharking, construction extortion, and more. The One Over Golf Club in Carroll Gardens was one of his hangout hubs—an underworld social club run by Joseph “Joe Pits” Conigliaro.

On December 24, 1988, Boriello took part in a high-profile Mafia induction ceremony. Alongside John Gotti Jr., Dominick “Skinny Dom” Pizzonia, Craig DePalma, and others, he joined the family officially. The ceremony was witnessed by power players John “Jackie Nose” D’Amico and Gene Gotti, and was orchestrated by Sammy Gravano himself.

Gotti elevated his own son to capo, forming the Junior Gotti crew—with Boriello as his second-in-command. The crew featured soldiers like John “Jackie” Cavallo, Charles Carneglia, and Tommy Cacciopoli, and associates such as Steve Kaplan and John Alite. They controlled rackets across boroughs, collecting tribute from strip clubs, handling rackets, and enforcing Gotti family needs.

In 1990, Boriello acted on direct orders from Gotti to eliminate Gambino soldier Louis DiBono, who had lobbied for a lucrative contract to install fireproofing at the World Trade Center. After DiBono's murder, Gravano assumed control of the contract.

On April 13, 1991, Boriello was ambushed and gunned down outside his Bensonhurst home. The hit—carried out by Lucchese captain Frank “Big Frank” Lastorino—was ordered by Lucchese underboss Anthony Casso after corrupted NYPD officers Louis Eppolito and Stephen Caracappa provided intel. Lastorino emptied his gun with seven shots—two to the head, five to the torso. Boriello collapsed beside his 1991 Lincoln Town Car, with his wife Susan and their children inside the house.