David Petillo (1908 – 1983) hitman, mafioso

Original Version March 2010.

Antonio Petillo from Pollico, Salerno south of Naples, emigrated to New York in 1885, and married Michelina, also an Italian immigrant, the next year. They had seven children – David was the sixth. Antonio was a sanitation worker and later a driver. He became a naturalized US citizen in 1910. 

David attended a public school sometimes, and left for good when he was 14. He became involved with Giosue Aiello, a criminal who ran an area in the Lower East Side of Manhattan around Cherry Street. Petillo became regarded as a finocchio, or even a fairy. At age 18 he was sent to Chicago where Al Capone was to straighten him out.

Aiello disappeared, probably killed, around 1920, and David Petillo, along with partner Charles “Chalutz” Gagliodotto, and others of Aiello’s crew, were initiated into the Lucky Luciano's  (Genovese) organization. 

Petillo and Gagliodotto were contracted to carry out murders for the bosses of the Detroit, Cleveland and Chicago Mafia organizations. It was during this time that “Little Davie” earned a reputation as the “cross-dressing killer”, as he often dressed in drag in order to get close to unsuspecting victims, although it was sometimes Gagliodotto (who had the advantage of being barely 5 feet/1.5m) in drag, and sometimes both. It is said that both dressed as female mourners for a funeral, complete with veils, and slipped into a car after their target to kill him without detection. The FBI estimated that Petillo and Gagliodotto were involved in as many as 30 murders.

In 1924, Petillo was charged with "jostling" (intentionally and unnecessarily placing one's hand in close proximity to another person's pocket or handbag) and given sixty days. That same year in October he was charged as Joseph Rose Richmond with attempted grand larceny, but discharged. He served a day in jail in May 1925 and in June, he was charged under the name Joseph Rose and given 30 days. He was charged again in October in Danbury, Connecticut with vagrancy: this time as Herbert Quell.

David married Madeline in 1928 or 29. In the 1930 federal census he gave his profession as a salesman. He had a unit on Canal Street buying odd lots, although other sources say that he was in Chicago as Al Capone’s bodyguard. 

In 1932 Petillo made his first trip to Italy with his sister Lavinia. He made another trip as part of Luciano’s entourage.

On return to New York, he reported to Lucky Luciano, and in 1936 he was arrested on ‘white slavery charges’ in a racket that grossed $12 million a year with over 3,000 prostitutes working at over 200 brothels. Enough women were happy to testify against him.

“Among the brothels Luciano and Petillo had under their proverbial thumb was one operated by the husband-and-wife team of Pete Harris and Mildred Balitzer. Harris pleaded guilty, and Balitzer turned state’s evidence. Balitzer testified about meeting both Little Davie and Charlie Lucky numerous times, and that she was required to collect from each of the girls at her brothel $10 a week which “bonded” them to the mobsters.” (Crawford, 2015 p 85).

“It was the gangster trial of the decade. After beer baron Dutch Schultz was shot to death in a New Jersey tavern, Luciano was declared public enemy number one on the East Coast. [Special Prosecutor Thomas E] Dewey vowed to take him down. Instead of narcotics or gambling, both of which fell under Luciano’s domain, Dewey went after what he saw as the gangster’s weak spot: his control of the city’s $12-million-a-year “vice rackets,” including two hundred brothels and two thousand prostitutes.

Indicted under his given name, Salvatore Lucanía, the trial of Charlie Lucky garnered daily headlines. Dewey depicted the crime lord pulling the strings as he strutted around his luxury suite in the Waldorf-Astoria in a silk robe. Luciano’s main instrument of terror and control over the prostitution ring was “Little Davie” Petillo, or Betillo as he often allowed his name to be misspelled.

'You guys are through,' a brothel operator testified he was told by Luciano. 'I am giving the business to Little Davie.' Those who resisted suffered beatings, bullets pegged in their direction, and guns and knives in the ribs, Dewey told jurors.” (Capeci & Robbins)

Petillo was sentenced to serve 25-40 years in New York State’s Sing Sing prison. Luciano was sentenced to 30-50 years. Later in 1936, authorities moved them to Clinton Correctional Facility in Dannemora, NY, a remote facility far away from New York City. At Clinton, Petillo prepared special dishes for Luciano in a kitchen set aside by authorities. After the US entered the Second World War, Luciano struck a deal with the  government to get Mafia co-operation re security on the New York waterfront to prevent Axis infiltration, and then provided Mafia contacts in Sicily to aid the Allied invasion in 1943. In return Luciano was released but deported to Italy. Petillo was still in prison.

David’s wife Madeline died in 1950; his parents returned to live in Salerno, Italy. Antonio Petillo died in 1954. One of David’s brothers, Roland, became an Italian police officer, and another an agent for the IRS.

David was paroled in 1955, and then trafficked heroin for the Genovese family though Lower East Side and Greenwich Village bars including the 82 Club (run by his cousin Anna Genovese (née Giovaninna Petillo).

He was arrested for violation of parole in June 1958, and on narcotics charges. He was returned to Clinton Correctional Facility for another nine years.

Gagliodotto was among 19 arrested in 1965 charged with being part of a $90-million-a-year narcotics ring. The defense attorney filed multiple motions and three years passed. Gagliodotto was particularly edgy, and was addicted to his product, the heroin. He accused two colleagues of stealing from him and executed them. The others thought that he had gone too far. Petillo, newly released from prison, agreed to deal with him, and took along his cousin Eddie Vassallo. Gagliodotto did not suspect his old partner, but Petillo and Vassallo, using a plastic bag, strangled him, and then left him on the street. The morgue doctors did not pay enough attention and put it down to a heart attack, until rumors reached the FBI and the job was done properly. However nobody was ever charged.

Petillo now, in the late 1960s, became involved in pornography until the business was sold to the Gambino family.

David, age 61, married for a second time in 1969 to Phyllis aged 19. They went on honeymoon to Italy and Greece. On a second trip to Italy in January 1973, David and Phyllis were arrested on arrival and quickly deported back to the US.

From 1975, Petillo lived in Brick Township, New Jersey, and was building up a new criminal crew, and running adult bookstores and gay health spas. In February 1980, after a dispute about ownership and profits, Petillo and three others shot and killed his cousin Edward Vassallo.

Petillo fled the US via Mexico after the murder. The FBI and Interpol tracked him as he moved between luxury hotels in Germany, Greece, Singapore, Bali, Hong Kong, and Hawaii. The trail ended three days after Christmas in 1983 when Petillo collapsed and died while staying in the resort town of Málaga, Spain, on the Mediterranean coast. He was 75. His body was returned to New York City for burial.

• John Martin. “Dewey’s Vice Raids Peril Police Jobs », Daily News, February 4, 1936.
• “Vice Ring Links Half of Nation”. The Reading Times, May 12, 1936.
• Tom Renner. “Mobster Reported Slain”. NY Newsday, August 28, 1968.
• Dorothy Hinchcliff. “Witness tells of carrying out mob’s orders to kill”. Asbury Park Press, May 19, 1982.
• “David Petillo”. "The FBI Files: David Petillo Did It in Drag". Friends of Ours: Mostly About Organized Crime,12/20/2010. Archive. 
• Eric Ferrara. “Petillo, David Silvio” in Manhattan Mafia Guide: Hits, Homes & Headquarters. History Press, 2011: 122-4.
• Phillip Crawford, The Mafia and the Gays. Kindle, 2015: 85-6.
• Jerry Capeci & Tom Robbins. Mob Boss: The Life of Little Al D’Arco the man who brought down the Mafia. St Martin’s Press, 2013.
• Jim Elledge. The Boys of Fairy Town: Sodomites, Female Impersonators, Third-Sexers, Pansies, Queers, and Sex Morons in Chicago’s First Century. Chicago Review Press, 2018: 82.

Wikitree(David Silvio Petillo, Antonio Petillo)

IT.Wikipedia(Dave Petillo)

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David’s family name is sometimes given as Betillo. Wikipedia spells it so when writing about Lucky Luciano. 

Neither Petillo nor Betillo is listed among the notable inmates on the Wikipedia page on Sing Sing prison.

Petillo almost certainly was not permitted to transvest while in prison, and there is no mention of any action afterwards. Therefore he had stopped by the age of 28.

See also The Murderers amongst us.