Benjamin Ruggiero aka Lefty and Lefty Guns (April 19, 1926 - November 24, 1994) was a member of the Bonanno crime family best known for his close association and mentorship of Federal Bureau of Investigation FBI undercover agent Joseph Pistone aka "Donnie Brasco".
Born in the fourth ward neighborhood of Manhattan, Ruggiero grew up in the Knickerbocker Village private housing development in Little Italy, Manhattan. Knickerbocker Village was home to many future members of the Bonanno family. Ruggiero joined the Bonanno family as a young man, serving as a street soldier under capo Michael Sabella. Ruggiero soon became successful in bookmaking, extortion and loansharking rackets. During this period, Ruggiero became good friends with future family boss Philip "Rusty" Rastelli and fellow mobster Anthony Mirra. Ruggiero was also a hitman, allegedly murdering at least 26 people during his criminal career.
Ruggiero became the part owner of a fishery in the Fulton Fish Market in Manhattan. As a part-owner, Ruggiero was able to put himself on the company payroll with a $5,000-a-month "no-show" job. During the 70's, Ruggiero also purchased a social club in Little Italy. Ruggiero relished his life as a mobster. He explained it this way to another Bonanno mobster (who was actually an undercover FBI agent):
"Tony, as a wiseguy you can lie, you can cheat, you can steal, you can kill people: LEGITIMATELY. You can do any goddamn thing you want, and nobody can say anything about it. Who wouldn't want to be a wiseguy?".
Ruggiero was a six-foot tall, lean-bodied man with a narrow face, intense eyes, slightly stooped shoulders, and a cigarette-raspy voice. Ruggiero reportedly earned his nickname from tossing dice left-handed while playing craps. He lived in an apartment on Monroe Street in Manhattan in the same building as his friend and fellow Bonanno mobster Anthony Mirra. Ruggiero reportedly owned a cigarette boat that he kept docked on the East River in New York.
Ruggiero had three daughters and one son, Thomas Sbano, with his first wife. In the late 1950s, Ruggiero left his first wife, eventually moving in with his future second wife, Louise. In September 1977, Ruggiero married Louise in a small ceremony at New York City Hall. Ruggiero was reportedly very protective and faithful to Louise, but not especially sensitive.
Ruggiero's son Thomas struggled with a heroin dependency until he checked into a drug rehabilitation center in 1979. After Thomas' release, Ruggiero got him a job at the Fulton Fish Market. Ruggiero's younger daughter worked at a New York hospital and managed a booth at the Feast of San Gennaro in Little Italy. Two of Ruggiero's daughters reportedly married mobsters. The Bonanno family allegedly discovered that Ruggiero's son-in-law Marco was cheating the family and told Ruggiero to eliminate him. Marco disappeared, and his body was never recovered.
Around the time that Ruggiero became a member of the Bonanno family, he met Donnie Brasco. Fellow mobster Mirra introduced Brasco, a small-time jewelry thief, to Ruggiero in a Manhattan bar. What Ruggiero didn't realize was that Brasco was really Joseph D. Pistone, an undercover FBI agent. Pistone's original mission had been to infiltrate a jewelry fencing ring; Pistone prepared for this assignment by taking gemology classes. However, the friendships Pistone developed (as Brasco) with Mirra, Napolitano, and Ruggiero now gave the FBI the chance to infiltrate the Bonanno family itself.
Brasco was soon placing bets with Ruggiero and helping him make collections for the bookmaking operation in Ruggiero's social club. Ruggiero became a mentor to Brasco and eventually sponsored him for membership in the family. Ruggiero's good relationship with Brasco soon caused friction with old friend Mirra, who had originally introduced Brasco to Ruggiero. Ruggiero and Brasco became good friends; Brasco served as best man at Ruggiero's 1977 wedding and frequently advised Ruggiero on handling his son's drug dependency.
At one point, Ruggiero almost discovered Brasco's true identity. Ruggiero and Brasco were sitting in a Miami Beach, Florida restaurant one day and Ruggiero was reading a copy of Time magazine. The article was about the infamous Abscam scandal and detailed how FBI agents posed as rich Arab businessmen to catch U.S. Congressmen taking bribes. What caught Ruggiero's eye was a picture of a white yacht that the FBI used to entertain the congressmen. Suddenly, Ruggiero recognized the boat; it was the same craft that Brasco had provided several months before for a party with Ruggiero and other Bonanno mobsters. Fortunately for Brasco, he was able to convince Ruggiero that this was a different yacht.
By the 1970s, Ruggiero had acquired a gambling dependency; he was betting and losing heavily on horse races at Aqueduct Racetrack in Queens. Soon he was borrowing money from mobster Nicholas Marangello to feed this addiction. By 1977, Ruggiero owed Marangello $160,000. The Bonanno family finally told Ruggiero that he would have to repay Marangello before he could become a made man, or full family member. By the summer of 1977, Ruggiero had paid most of his debt to Marangello and the family accepted his membership. However, by 1978, Ruggiero was back in debt again to Marangello. To settle the debt this time, the family arranged to transfer the revenues from part of Ruggiero's criminal operations directly to Marangello. Due to his gambling problem, Ruggiero was always trying to hide his few assets from his creditors Marangello and Sabella, and was always scheming on how to make money.
During a later criminal enterprise, Ruggiero met the mafia boss of Milwaukee, Wisconsin. During the process of collaborating a scam in Milwaukee, Ruggiero openly admitted to Pistone that he felt threatened while in the presence of Milwaukee mob boss Frank Balistrieri. In 1979, Ruggiero converted his social club into a candy store and gave it to one of his daughters to manage. At the same time, Ruggiero and Brasco started a bookmaking operation out of the store. However, Ruggiero was soon dropped from the partnership because he was unable to provide the initial required investment of $2,500.
In 1979, Bonanno boss Carmine Galante was murdered, creating a power vacuum in the family. After Galante's murder, Philip Rastelli took over, running things from prison. However, one faction in the family rebelled at Rastelli's assumption of leadership. At this time, Ruggiero joined the crew of Dominic "Sonny Black" Napolitano, a strong Rastelli supporter. On May 5, 1981, three rebel capos were lured to a meeting and murdered. Alphonse Indelicato's body was discovered in a vacant lot in Queens, but the bodies of Philip Giaccone and Dominick Trinchera were never found. Ruggiero and Napolitano were prime suspects in these murders. After the deaths of the three capos, the rebellion against Rastelli was quashed.
In 1981, the FBI decided to end the Brasco investigation and terminate Pistone's assignment. FBI agents soon visited both Ruggiero and Napolitano at a social club and informed them of Brasco's true identity. After the Bonanno leadership learned the truth about Brasco, they immediately went after the men who brought Brasco into their midst. Mirra and Napolitano were murdered, and a contract was put out on Ruggiero. On August 30, 1981, the FBI intercepted Ruggiero as he was going to a meeting at Marangello's social club and placed Ruggiero under protective custody. If Ruggiero had attended that meeting, the family would have murdered him.
After the FBI put Ruggiero in protective custody, they tried several times to persuade him to become a government witness and join the Witness Protection Program. However, Ruggiero refused to cooperate with the FBI and even tried to bail himself out of jail. In 1982, Ruggiero was charged with violations of the Racketeer Influenced and Corrupt Organizations Act (RICO Act) in both New York and Florida. The specific charges included conspiring to murder the three capos in New York, distributing methaqualone in New York, and committing extortion, the planning of a bank robbery, and the running of illegal gambling operations in Florida.
Ruggiero was convicted in both New York and Florida and sentenced to 20 years in prison. In 1992, Ruggiero was released from prison after serving 11 years, sick with lung and testicular cancer. On November 24, 1994, Benjamin Ruggiero died of lung cancer at age 68.