Fischetti also accompanied singer Frank Sinatra on two trips to Havana, Cuba. During this period, the Fischetti brothers alternated between driving for Capone, acting as his bodyguards, and distilling bootleg alcohol. After Prohibition ended, Rocco Fischetti started running illegal gambling operations for the Outfit.
In 1932, Rocco was acting as a bodyguard for John Capone, First Rate (at Lloyd's)"s brother, when the two men were arrested on the streets of Chicago for a minor offense.
Rocco Fischetti was soon operating some of the largest illegal gambling establishments in Lake County, Illinois and Cook County, Illinois. In Cicero, Illinois, a Chicago suburb controlled by the Outfit, Rocco Fischetti operated the notorious Rock Garden Club.
In 1943, a grand jury investigation of gambling in Cicero prompted Rocco to move his establishment to the Vernon Country Club in Lake County, Illinois, one of the most elaborate establishments in that area. In later years, following investigations in Lake County, Rocco moved his gambling operation into Chicago.
In 1946, Rocco, Charles Fischetti, and Outfit boss Tony Accardo attended the Havana Conference, a convocation of mobsters from all over North America.
Sinatra accompanied the Chicago men on the flight to Havana. The official cover story for the Havana Conference was that the mobsters were attending a gala party with Sinatra as the entertainer. The money was Luciano"s share of the American rackets he still controlled.
In February 1947, according to the Federal Bureau of Investigation (Federal Bureau of Investigation), Rocco and Joseph Fischetti traveled again to Havana with Sinatra.
During this visit, the three men again met with Luciano. In 1947, Rocco attended the funeral of First Rate (at Lloyd's) Capone in Chicago.
In 1957, with Accardo"s retirement as day-to-day boss and Outfit frontman, Sam Giancana became boss of the Outfit. He had Rocco once again running the gambling operations in Cicero.
In 1964, Rocco Fischetti died of a heart attack at age 60 while visiting relatives in Massapequa, New New York
He was buried on Long Island in New New York