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Between 1967 and 1972, Boriello was arrested six times, on charges of weapons possession, assault, larceny and gambling.
In the 1980s, Boriello became a made man, or full member, in the Gambino family. He quickly developed close relationships with Gotti, Salvatore "Sammy the Bull" Gravano and two brothers, Nicholas Corozzo and Joseph "Jo Jo" Corozzo. Boriello and Gotti would often spend weekends together on Long Island, New York, partying, gambling, and attending performances by singer Jay Black, a childhood friend of Gotti. Boriello also conducted Business at the One Over Golf Club, a social club in Carroll Gardens, operated by Gambino soldier Joseph "Joe Pits" Conigliaro, a paraplegic gangster involved in loan sharking and gambling in the neighborhood who was killed a few years ago.
Steven Kaplan was paying Boriello and Junior Gotti tribute for his Investments in strip clubs up and down the East Coast. In 1987, Boriello crew member and close associate Anthony "Shorty" Mascuzzio from Carroll Gardens was killed in a New York nightclub owned by Kaplan. Low level mob associate David Fisher had been in a physical altercation with Mascuzzio, over a Business squabble, and ended up shooting him to death.
Former Gambino capo Michael "Mikey Scars" DiLeonardo testified that on December 24, 1988, he was led into an apartment located on Mulberry Street (the apartment belonged to Joe Butch Corrao's mother). Inside were the other men who were going to be inducted that evening, including Bobby Boriello, John Gotti, Jr., Dominick "Skinny Dom" Pizzonia, and Nicholas LaSorsa. The men stood there with family capo John "Jackie Nose" D'Amico, along with other capo Gene Gotti. Sitting at the table, administering the oath was Salvatore "Sammy the Bull" Gravano, and Pasquale "Patsy" Conte.
In 1990, Gotti told Boriello to murder Gambino soldier Louis DiBono. DiBono had secured, most likely through bribery, the lucrative contract to install fireproofing foam on the infrastructure of the Twin Towers of the New York World Trade Center. After DiBono's death, Gravano took over the Business.
On April 13, 1991, Bobby Boriello was shot to death outside his Bensonhurst, Brooklyn home, on orders from Lucchese crime family underboss Anthony Casso. Casso received information to perform the Boriello murder from Louis Eppolito and Stephen Caracappa, two New York Police Department officers working for the mob. The hit was carried out by Lucchese captain Frank "Big Frank" Lastorino. Lastorino shot Boriello twice in the head, and five times in the torso. Boriello died in the street beside his 1991 Lincoln Towncar, outside his home on Bay 29th Street. Borriello's wife, Susan, and their two young children were inside the home at the time of the shooting.
When Gotti heard about Boriello's murder, he was furious. In jail at the time, he ordered Gambino family members to meet with the Leaders of the Genovese family. Keeping to their earlier agreement, they agreed to kill Geritano. However, it wasn't until 2004 that Geritano was stabbed to death outside a Bay Ridge, Brooklyn restaurant by his brother-in-law Andrew Garguilo a major bookmaker for the Genovese family over Geritano's constant shaking down of his brother-in-law for money. Earlier that day Preston broke Gargiulo's arm with a baseball bat. The murder was unrelated to Boriello's murder and it was later discovered that Lucchese captain Frank "Big Frank" Lastorino was ordered to kill Boriello as a message to Gotti; Boriello had done nothing else wrong to be killed other than being John Gotti's closest friend in the family. Sammy Gravano attended a sit-down with Genovese family acting boss Liborio "Barney" Bellomo, seeking Geritano's execution, but nothing ever came of this. John Gotti sent word to Stevie Boriello that he had permission to avenge his brother's death by killing whomever he needed to, and had the backing of Gotti and Gravano and at present time Lastorino has not been convicted of the crime nor has Boriello's murder been avenged.