Why Frank Sinatra Was Banned From the Kennedy White House, Despite His Close Friendship With the President

One of the most infamous friendships that came out of the 1950s was between the King of Hollywood, Frank Sinatra, and politician John F. Kennedy. The two became fast friends and maintained a solid relationship into Kennedy’s presidency. However, Sinatra’s dealings behind closed doors soon caused his friendship with Kennedy to fall apart, ultimately resulting in the musician being banned from the White House.

Frank Sinatra John F. Kennedy
Frank Sinatra and John F. Kennedy | GAB Archive/Redferns

Frank Sinatra and John F. Kennedy had a powerful friendship

While it’s unclear when exactly Sinatra and Kennedy met, their friendship was apparent in the early ’50s when both were climbing the social ladder.

At the time, Sinatra, who was a member of the famous Rat Pack, had become well acquainted with Kennedy, who had just started his congressional career having been elected to the House of Representatives and then obtaining a seat on the Senate in 1953.

A few years later, in 1960, Kennedy announced his run for the presidency and got to work on his burgeoning campaign. But he needed some celebrity endorsements to influence the union vote.

Given his influence as a top-selling recording artist and A-list movie star, Sinatra was one of the many entertainers who endorsed the rising politician, and suddenly, their friendship was in the spotlight.

Frank Sinatra and John F. Kennedy
Frank Sinatra and John F. Kennedy | GAB Archive/Redferns

RELATED: Sammy Davis Jr. Always Held a Grudge Against John F. Kennedy

In early February 1960, Sinatra introduced Kennedy as the “next president of the United States” following a performance with the Rat Pack at the Sands Hotel and Casino in Las Vegas.

But Sinatra’s support didn’t stop there.

In addition to influencing his fans and fellow celebrities to vote for Kennedy, Sinatra also organized donor dinners, appeared in radio ads, and lent his private jet to Kennedy’s administration. At concerts, he would perform a reworked version of his hit “High Hopes,” which served as the theme song of the campaign.

From an outside perspective, Sinatra and Kennedy were a match made in heaven. However, just like all great things, the pair’s friendship soon came to an unexpected end.

Many were suspicious of Frank Sinatra’s intentions

Though Sinatra and Kennedy were great pals, not everyone accepted their friendship.

According to Biography.com, Kennedy’s wife, Jackie Kennedy, despised the singer and didn’t want him anywhere near the politician after he became President in 1961.

Frank Sinatra and Jackie Kennedy
Frank Sinatra and Jackie Kennedy | GAB Archive/Redferns

RELATED: Frank Sinatra Was Tracked by the FBI for Over 40 Years

It’s also been reported that Kennedy’s brother, Robert, had reservations about Sinatra and was even warned to separate the two after learning about the singer’s secret dealings.

Town & Country reports that the Attorney General was made aware of Sinatra’s connections to the mob after being provided ample evidence of the singer’s close relationship with Sam Giancana and other notorious gangsters.

According to the outlet, FBI’s J. Edgar Hoover played Kennedy recordings of Giancana demanding Sinatra to influence the administration to ease some attention off the mob. The wiretaps captured the singer telling Giancana he was working on getting information out of the Kennedys’ sister, Pat, with who he was allegedly having an affair.

After that, Sinatra was immediately kicked out of Kennedy’s inner circle, and his friendship with the President was never salvaged. The singer was even banned from the White House.

But despite Sinatra and Kennedy’s bond being short-lived, it continues to be one of the most powerful celebrity friendships in American history.