John F. Kennedy and Frank Sinatra; they were two of the biggest names in 1960s America. The pair met for the first time in the Mafia-ran Sands Hotel, Las Vegas and immediately bonded. Sinatra provided Hollywood women and glamour, while Kennedy offered the class of high-society. Their shared love for partying and womanising was reckless; One of Kennedy’s flames, Judy Campbell, was seeing the leader of the Chicago Outfit, Sam Giancana. With their criminal connections and Sinatra’s A-list fame and support, Kennedy became president in 1960. Yet despite helping him into the White House, the Chicago Outfit were acutely targeted by the Kennedy administration.
Discovering a love entanglement running in contradiction to a determined law enforcement policy against organised crime, FBI director J. Edgar Hoover sat down with the president. On the eve of a visit to Sinatra’s home in California, Kennedy abruptly cut all links with the Mafia including Sinatra and Campbell. Sinatra was devastated and humiliated and the pair never spoke again.