Long-time Genovese soldier David Petillo did it in drag.
Petillo was born in NYC in 1908, and during "his early teens was reputed to be a 'fairy,' but . . . when he was 18 or 19 years old he went to Chicago where he was 'straightened out' by AL CAPONE" according to FBI documents. Although Petillo may have "straightened out," he nevertheless had a fetish for dressing in drag when he killed his numerous victims over the decades.
The cross-dressing gangster left Capone in Chicago for Charlie "Lucky" Luciano in New York, and on February 1, 1936 was arrested on white slavery charges "with 100 prostitutes and madams and was described as an individual who had organized 200 houses of prostitution under LUCIANO with 3,000 girls grossing $12 million a year." The girls were happy to testify against Petillo, and he served 20 years at Sing Sing until paroled in 1956.
Upon his release from Sing Sing Petillo trafficked heroin for Vito Genovese through his gay bars, and in the mid- and late-1960s allegedly had a hidden interest in an afterhours club at 11 East 16th Street. Petillo further became involved in the pornography racket, and during the late 1960s and early 1970s was suspected of having an interest in Arrow Laboratories which produced some of the more hardcore material available at the time. Throughout the 1970s Petillo was "active in operation of sex-related businesses in New York City" and cocaine trafficking.
On February 4, 1980 Petillo murdered Edward Vassallo a/k/a/ Charles Talbot, and fled the country. He died in Spain on December 28, 1983, and no word on whether Petillo was buried in a dress.
Download David Petillo FBI Files Part I
Download David Petillo FBI Files Part II
Download David Petillo FBI Files Part III
Download David Petillo FBI Files Part IV
Download David Petillo FBI Files Part V