2. Marilyn Monroe
Out of all the celebrities on this list, none has had a relationship with organised crime that ended as badly as Marilyn Monroe’s. Some say that the star’s tragic death at the age of 36 can be directly attributed to the mafia.
It’s rumoured that Monroe spent her last night alive with known gangster Sam Giancana. She had met the mobster through dating Frank Sinatra in the sixties – the Rat Pack was known to have associated with the criminal underworld.
Giancana had a long and close relationship with the Kennedys and was allegedly trying to convince Monroe that the actress shouldn’t publicly announce her affair with then-president John F. Kennedy. The next day, Monroe was found dead – the cause of death was “apparent suicide.”
In 1982, private detective Milo Speriglio claimed in his book that Monroe was murdered by union leader Jimmy Hoffa in collaboration with Giancana.
1. Frank Sinatra
Has there ever been any celebrity so closely associated with the mafia as Frank Sinatra? The greatest of all the crooners already had a family connection to the mob before he hit the big time. Sinatra’s uncle, Babe Garavante, was involved with Willie Moretti’s gang, and he was convicted of murder in 1921 after driving the getaway car from an armed robbery. Even Sinatra’s parents were known to do business with mobsters.
Sinatra and his Rat Pack was said to have close relationships with organised crime, befriending famous gangsters such as Bugsy Siegal and Lucky Luciano. Sinatra was even said to be friends with Al Capone’s bodyguards.
Old Blue Eyes’ was also rumoured to have associations with the Gambino, Genovese, and Colombo families, something he always denied. But despite his claims of innocence, the FBI kept files on Sinatra that spanned five decades. His connection to racketeering investigation subjects had put the singer/actor firmly in the Bureau’s radar.