Benjamin “Lefty” Ruggiero – A True Account of Al Pacino’s “Lefty” in Donnie Brasco

Benjamin “Lefty” Ruggiero, also known as “Lefty Guns” and “Lefty Two Guns,” was born in the Fourth Ward neighborhood of Little Italy, Manhattan, on April 19, 1926. From a young age, Ruggiero became involved with the Bonanno crime family, serving as a street soldier under Michael Sabella. He lived in Knickerbocker Village, an apartment complex on Monroe Street, where he developed a fascination with fish, maintaining several saltwater and freshwater fish tanks in his apartment.

Ruggiero’s close friend, Tony Mira, also lived in the complex and was pivotal in introducing Ruggiero to FBI agent Joseph Pistone, who was undercover as Donnie “Don the Jeweler” Brasco. Pistone posed as an unconnected jeweler dealing in stolen goods, part of an elaborate FBI sting operation aimed at infiltrating the mob. As a Bonanno soldier, Ruggiero was deeply involved in bookmaking, extortion, loansharking, and enforcing the family’s will, earning him a reputation as a feared Mafioso and killer.

Ruggiero once explained his love for the mob life to Brasco, saying, “Donnie, as a wise guy, you can lie, cheat, steal, and 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 wise guy?” This mindset and his ruthless approach to mob life earned Ruggiero his nickname “Lefty” for his left-handed dice throwing and “Two Guns” because he always carried two guns during a hit, understanding that the old, unreliable guns often used by the mob could easily misfire.

Ruggiero’s gambling habit, however, led him into significant debt. By 1977, he owed over $160,000 to fellow Bonanno soldier Nicholas Marangello. To become a made man in the Bonanno family, Ruggiero had to repay this debt, which he managed to do, earning his place as a made man in late 1977.

Mira introduced Ruggiero to Donnie Brasco in 1977, and the two quickly became close. Ruggiero brought Brasco into the mafia fold, introducing him to various made members and getting him involved in his bookmaking operations. By 1979, however, the Bonanno crime family was in turmoil. The assassination of boss Carmine “Cigar” Galante created a power vacuum, leading to internal strife as various caporegimes vied for control.

Ruggiero’s capo, Dominick “Sonny Black” Napolitano, played by Michael Madsen in the 1997 movie Donnie Brasco, was crucial in the ensuing conflict. Sonny Black aligned himself with the new boss, Rusty Rastelli. He led a faction against rival capos Caesar Bonventre, Philip “Lucky Phil” Giaccone, Dominick “Big Trin” Trinchera, and Alphonse “Sonny Red” Indelicato. Loyal to Sonny Black, Ruggiero stayed close, knowing he would likely be involved in any violence that followed.

On May 5, 1981, the three rival capos were lured to a meeting under the pretense of negotiating a truce. Instead, they were murdered. According to Pistone, those involved in the murders included Sonny Black, Joe Massino, Sal Vitale, and several others, with Ruggiero serving as a lookout and later helping to clean up the crime scene.

Following these murders, the FBI decided to end their operation. Agents approached Ruggiero and Napolitano, revealing Pistone’s true identity. While the men initially dismissed the FBI’s claims as a trick, Napolitano was duty-bound to investigate. On August 17, 1981, Napolitano was summoned to a meeting to discuss Pistone and was killed for allowing the FBI to infiltrate the family. (In the film Donnie Brasco, Ruggiero is depicted as being killed, but this is inaccurate.)

Shortly after Napolitano’s murder, the FBI intercepted information that a contract had been placed on Ruggiero’s life. Fearing he would be next, the FBI picked up Ruggiero on August 30, 1981, as he headed to a meeting at Marangello’s social club, where he was likely to have been killed. They offered him witness protection in exchange for his testimony against the Bonanno family, but Ruggiero, citing the mob’s code of silence, or Omerta, refused.

In 1982, Ruggiero was charged with RICO violations, including conspiracy to murder the three capos, drug distribution, extortion, planning a bank robbery, and illegal gambling. He was sentenced to twenty years in prison. His refusal to testify earned him a “pass” from the Bonanno family, and the contract on his life was lifted.

While in prison, writers and movie producers reportedly offered large sums of money to Ruggiero for his story. Still, he remained true to his oath, declining all interviews and offers. He served his sentence and was released in 1992. Officially retired from the mob, Ruggiero lived quietly until his death on November 24, 1994, from lung and testicular cancer, likely a result of his lifelong habit of chain-smoking English Oval cigarettes. He was 68 years old.