Sinatra and The Jack Pack

Sinatra and The Jack Pack

During the late 1950’s two of the most famous Americans of the 20th Century came together in a way that was not commonly known at the time, and the results were an explosive series of events that went close to creating a national scandal of colossal proportions.

The two Americans in question were Frank Sinatra and John Fitzgerald Kennedy, and the circumstances that brought both to the brink of destruction remained largely unknown to the general public right up until recent times.

Frank Sinatra had become perhaps the world’s best-known entertainer during the 1940’s and 50’s both as a singer and movie star. However following the end of the Second World War his fortunes had waned as musical tastes changed and his popularity fell.

He also made a bad career move in 1946 when he was seen in Cuba in the company of Lucky Luciano, a major Mafia figure of the time. Sinatra had several friends in the Mafia, acquaintances that had developed from his early days in show business.

These relationships were well known to the head of the FBI, J. Edgar Hoover – a person of immense power – and a great disliker of Sinatra.

However,  Sinatra managed to secure the plumb roll of Private Angelo Maggio in the 1953 blockbuster movie, “From Here to Eternity”, reportedly enlisting the help of old friends in the Mafia to do so.

The film re-launched Sinatra’s career to dizzying heights, and around this time he developed a close friendship with the rising political star John F. Kennedy, widely known as JFK. Sinatra had long been a Democrat supporter and the two men shared other common ground – notably the love of a good time, including the company of beautiful women who Sinatra could introduce to Kennedy from his Hollywood contacts.

Backing Kennedy was his so called “Jack Pack” – the JFK campaign team that directed his push towards the White House. They regarded the support of Sinatra as solid gold that would provide a tremendous publicity boost leading up to their Presidential bid.

Sinatra was a tireless worker for Kennedy all through the Presidential campaign of 1960 when he approached his old Mafia friend Sam Giancana for electoral assistance – that of encouraging people to vote Democrat. This service was provided free of charge.

Kennedy was elected President in November 1960, and Sinatra organised an Inaugural Gala function that turned out to be a first-rate show business production in its own right. Nat King Cole, Laurence Olivier, Harry Belafonte, Ethel Merman, Jimmy Durante, Gene Kelly, Milton Berle, Janet Leigh, Tony Curtis, Bette Davis, as well as Sinatra himself all took the stage. Kennedy personally thanked Sinatra for all his campaign work and to all intents and purposes the relationship between the two men was at an all time high.

But behind the scenes an intricate series of complications had developed that would abruptly change the landscape. For some time, Kennedy had been having an affair with a young woman, Judith Campbell, who had been introduced to him by Frank Sinatra – a situation that Hoover and his FBI team was aware of. However, at the same time she began an affair with the Mafia operative Sam Giancana and this greatly upset Hoover – who was already outraged by Sinatra’s Mafia connections.

President John Kennedy’s brother, Bobby was the US Attorney General and he had made it a personal priority to attack the Mafia and its influence on America’s affairs.

This generated a further layer of complication into the already tangled web of forces that had been unleashed.

Hoover confronted Kennedy with all these facts in the spring of 1962 when he learned that Kennedy was planning to stay at Sinatra’s Palm Springs residence during an official visit to California. Hoover demanded that Kennedy sever his contacts with Campbell and Sinatra or risk public exposure. As the situation involved the President in an extra marital affair and having connections with the Mafia it was feared that that a scandal of seismic proportions would follow that could well bring down the Presidency.

After a hurried family conference, Kennedy agreed to Hoover’s demands, and informed Sinatra that the relationship was over – sending Sinatra into a violent rage. The Mafia were also greatly irritated as they felt that they deserved some reward, or at least a degree of immunity from being attacked, after helping with JFK’s election.

Sinatra never forgave Bobby, who be blamed for the situation and withdrew his support for the Democrats thereafter. He instead got behind the Republicans, later establishing


By: R. Whitaker

Image: Photo of Frank Sinatra, American singer, circa 1947, courtesy of Wikimedia Commons.