During this period, the Fischetti brothers alternated between driving for Capone, acting as his bodyguards, and distilling bootleg alcohol.
In 1932, Rocco was acting as a bodyguard for John Capone, Al's brother, when the two men were arrested on the streets of Chicago for a minor offense.
In Cicero, Illinois, a Chicago suburb controlled by the Outfit, Rocco Fischetti operated the notorious Rock Garden Club.
In 1946, Rocco, Charles Fischetti, and Outfit boss Tony Accardo attended the Havana Conference, a convocation of mobsters from all over North America.
In February 1947, according to the Federal Bureau of Investigation (FBI), Rocco and Joseph Fischetti traveled again to Havana with Sinatra.