Investigators say that Ugo Gabriele prefers to use the name Kitty, The Daily Telegraph reported. Gabriele was picked up with 27 other alleged members of the Camorra, the powerful mob in Naples.
Gabriele, 27, allegedly ran a drug and prostitution operation for the Scissionisti clan.
Italian police told The Daily Telegraph that Gabriele appears to be the first cross-dressing transsexual from any of the country's four major criminal organizations.
The mob groups have a reputation for intolerance of homosexuality.