On this day in 1976 one of the main players in the Chicago Outfit, Johnny Roselli, died at the age of 71. Johnny helped the Outfit control the Las Vegas strip during the 40’s and 50’s, and by the time the 60’s had come around he found himself being unknowingly recruited by the Central Intelligence Agency in a plot to assassinate Cuban leader Fidel Castro.

In 1975 and in 1976 he stood before a US Senate Committee to testify in the plan to kill Castro, and then another committee to testify about the conspiracy to kill President Kennedy. During this period Roselli went missing, and would later be found rotting in a 55-gallon drum that was floating in a bay near Miami.

On this day in 1976, one of the most enigmatic and dangerous figures in American organised crime met a gruesome end. Johnny Roselli, a key player in the Chicago Outfit and a man who had rubbed shoulders with the most powerful criminals and intelligence operatives in the country, was found decomposing inside a 55-gallon oil drum floating in Dumfoundling Bay, near Miami, Florida. He was 71 years old. His murder remains officially unsolved, though few who knew the world Roselli inhabited were surprised that it ended this way.

Born Filippo Sacco in Esperia, Italy in 1905, Roselli emigrated to the United States as a child and eventually reinvented himself with a new name and a burning ambition. He worked his way up through the bootlegging rackets during Prohibition, catching the attention of Al Capone's Chicago Outfit before becoming a trusted operative on the West Coast. Suave, well-dressed, and charming enough to move between boardrooms and backrooms with equal ease, Roselli became the Outfit's primary representative in Las Vegas during the 1940s and 1950s, helping to oversee the mob's stranglehold on the casino industry at a time when the Strip was little more than a stretch of desert ambition and dirty money.

By the early 1960s, Roselli had entered far more dangerous territory. The Central Intelligence Agency, desperate to remove Fidel Castro from power following the Cuban Revolution, quietly made contact with organised crime figures who had lost their lucrative Havana casinos after Castro's takeover. Roselli, along with mob bosses Sam Giancana and Santos Trafficante, was recruited into a series of CIA-backed assassination plots against Castro. Whether Roselli fully understood the extent to which he was being used as a disposable asset is debatable, but he played his part nonetheless.

His troubles deepened in 1975 and 1976 when he was called before two separate United States Senate committees. The first concerned his role in the CIA-Castro assassination plots, the second involved testimony related to the assassination of President John F. Kennedy. That Roselli knew something significant about the latter has long been suspected by historians and researchers. Just weeks after his second round of testimony, he vanished. His body was discovered on 9th August 1976, and the manner of his death — bound, stuffed into a drum, and dumped at sea — bore all the hallmarks of a professional mob execution carried out by people who wanted him silenced permanently.

Johnny Roselli's story stands as one of the most compelling and troubling threads running through mid-twentieth century American history, sitting at the dark intersection of organised crime, Cold War politics, and presidential assassination. His life and death continue to fuel serious debate about how much the underworld truly knew about the events of 22nd November 1963.