Why Frank Sinatra Was Banned From The White House, Despite Being Close Friends With The President

Frank Sinatra; John F. Kennedy: have there ever been bigger icons of American culture? Though these two powerful men came from very different backgrounds, the pair maintained a close friendship and working relationship. That is until the F.B.I. got involved, however – and the agency’s shocking discovery meant the two would never be on speaking terms again.

Like any great story involving Ol’ Blue Eyes, Sinatra and Kennedy’s story could only have started in one place: Las Vegas. It was here while performing with the Rat Pack that the “My Way” singer met the politician’s sister, Pat Kennedy Lawford, in the 1950s. And it was through her that the two began an – almost – inseparable friendship.

At this point in his political career, Kennedy was at a kind of slump. Having been elected to the Senate in 1952, the politician was growing fatigued with only being able to oversee events in his native Massachusetts. What he wanted was a bigger platform: a presidential platform. But to get there, he needed all the help he could get.

Befriending Sinatra, then, was a godsend for Kennedy’s career. In the 1950s, the crooner was hitting a new high and finding a new audience beyond the bobby soxers of his early days. Besides recording some of his most acclaimed music this decade, the singer had also gained a new fanbase through a successful film career.

Plus there was the fact the crooner was on Kennedy’s side politically. Born to a mother who served as a Democratic Party committeewoman, Sinatra learned about politics at an early age. As quoted by Sinatra.com’s Steve Pond in 2011, Sinatra once said, “I just think it is the duty of every American citizen to take part in political races and vote.”

And take part he did! Throughout his career, the star rubbed shoulders with political leaders such as Franklin D. Roosevelt, who once invited him to the White House. He then lobbied publicly for Harry S. Truman during the presidential successor’s re-election in 1948, as well as Adlai Stevenson’s unsuccessful presidential bids in 1952 and 1956.

Yet Sinatra’s activism didn’t stop with aiding political campaigns. A believer in civil rights, the crooner blackballed venues that wouldn’t let African Americans through the door. For a performer such as Sinatra, this could have had negative effects on his career. But as he himself once said, “When I believe in a person or an idea or a cause, I go all out in my efforts regardless of possible consequences.”

There was also another thing that Sinatra and Kennedy had in common: a love for the high life. Through his brother-in-law Peter Lawford, Kennedy was a regular attendee at the Rat Pack’s rowdy social functions. There, the politician became friends with Sinatra who subsequently made Kennedy acquainted with other stars such as Marilyn Monroe.

Through their similarities, Sinatra and Kennedy quickly formed a strong bond. And when the latter announced their bid for presidency in 1960, it was a no-brainer that the singer would get involved too. As he did for Truman and Stevenson, Sinatra began flexing his political muscles and was soon working his magic on Kennedy’s campaign.

While his friend wowed at rallies, Sinatra was busy recording promos and fraternizing with potential donors. He even gave Kennedy his song “High Hopes” to use as a campaign song. But Sinatra’s strongest endorsement came during a Rat Pack show in February when the crooner told his audience that Kennedy – in attendance at the gig – would be the “next president of the United States.”

When Kennedy won the campaign in November, it was Sinatra who had front row seats for the ensuing festivities. In a celebration at the National Guard Armory in Washington D.C., the singer sat right alongside the politician and his family. Later in the evening, Kennedy praised his friend’s during a victory speech from the venue’s stage.

Even though Sinatra’s patronage undoubtedly helped Kennedy’s election victory, the star wasn’t loved by everyone in the politician’s circle. Notably, the president’s wife Jackie is believed to have had a bad feeling about Sinatra from day one. But it seems that the First Lady may have had a point – after all, Sinatra famously kept some very bad company.

These days it’s routine for open secrets about a celebrity’s private life to become tabloid fodder. And in Sinatra’s day, it was his own rumored connections with the mob that made headlines throughout the nation. His link with organized crime was so famous that it even purportedly inspired the character of Johnny Fontane in The Godfather.

The alleged connection apparently began in Sinatra’s early years as a singer. Back then, the only gigs the fledgling star could get were in mob-owned bars and clubs that sprang up in response to strict Prohibition laws. So night after night, Ol’ Blue Eyes would earn his keep entertaining New York’s criminal underground.

Now we know what you’re thinking: playing to gangsters doesn’t automatically make you a member of the mob. Even Sinatra himself made that argument in response to his past. As quoted by Owen Williams on Medium in 2019, the crooner reportedly quipped, “If St. Francis of Assisi was a singer and worked in saloons, he’d have met the same guys. That doesn’t make him part of something.”

But Sinatra’s involvement seemed to grow deeper when he took his first steps towards national stardom. Unhappy with working under bandleader Tommy Dorsey, the musician turned to notorious hood Willie Moretti, who “persuaded” Dorsey to reconsider their contract. “Willie fingered a gun and told me he was glad to hear I was letting Frank out of our deal,” Dorsey told Parade magazine in 1956. “I took the hint.”

Once he’d earned his celebrity status, Sinatra became even closer with his wiseguy friends. It was rumored to be the mob who kept the singer from serving in the Army during World War II. And it was reportedly gangster Johnny Roselli who convinced studio heads to cast him in 1953’s From Here to Eternity – a role that helped revive Ol’ Blue Eyes’ ailing career.

Things really came to a head in 1947 when photographs of the star attending a party for mobster Lucky Luciano in Cuba emerged. While Sinatra contended that he had been there merely at the behest of a talent agent, others offered a different story. Actor Jerry Lewis, for example, claimed that he’d been there to smuggle $2 million of mob money back into America.

Whether he was married to the mob or not, Sinatra nevertheless carried the rumor of being a made guy everywhere he went. And the press weren’t the only ones who’d paid notice to the Chairman of the Board’s activities either. It had even caught the attention of the United States’ premier crime fighters too: the F.B.I.

Already suspicious of Sinatra’s ability to woo over bobby soxers, the Bureau’s director J. Edgar Hoover opened an investigation into the singer in 1943. But with Ol’ Blue Eyes’ rumored mob connections, their file kept getting bigger. By the time of Sinatra’s death six decades later, his case file was longer than the line to one of his concerts.

Most of these files detailed surveillance jobs against the star. On countless occasions, Bureau agents would watch Sinatra meeting and partying with notorious gangsters. “Those were his friends,” former-fed Sam Ruffino explained to The Gangster Report in 2015. “The fact that they were known hoodlums and murderers didn’t matter to him.”

They may have been his friends, but Sinatra wasn’t above throwing them under the bus to escape injury. Having become aware of his reputation, the singer contacted Hoover in 1950 with the aim of becoming an informant. That year, he also named Moretti and other goodfellas such as Bugsy Siegel as friends during an interview with U.S. senators.

In the end, Sinatra’s case history had no real impact on his life or career. Yet it would go on to affect his relationship with Kennedy. Taking a firmly anti-crime stance, Kennedy and his brother Robert targeted mobsters such as Sam Giancana during their time in power. So obviously spending time with a man with a rap sheet such as Sinatra’s wasn’t good for their image.

As the legend goes, Hoover approached Robert Kennedy shortly after his brother entered the White House. During their meeting, the F.B.I. director showed him evidence that their pal Sinatra was in cahoots with gangsters – including Giancana. When word got back to the President, this was enough for him to sever ties with the crooner for good.

An interesting theory, yes, but it’s one that has some obvious inconsistencies. For one, Sinatra’s mob ties were an open secret, and his alleged affiliations were plastered across countless tabloid front pages. Surely a man as wise to the world of celebrity as Kennedy would have already known of Ol’ Blue Eyes’ checkered past?

What’s more, it seems that Kennedy may even have knowingly benefited from the star’s mafia connections during his presidential campaign. Reportedly, Sinatra played gigs for Giancana in return for the mobster putting in a good word about Kennedy to union voters. More bizarrely than that, the President and Giancana – with Sinatra acting as go-between – allegedly worked on an attempt to overthrow Cuba’s Fidel Castro.

It seems likely then that Kennedy was already well aware of Sinatra’s ties. So if this was the case, what was it in fact that made the President end his friendship with the crooner for good? Well just like everything in life, it seems there’re two sides to every story. And this one doesn’t paint the Chairman of the Board in a very favorable light.

Released in 2018, Lee Server’s Handsome Johnny contained new testimony on the split from Joe Shimon. A former detective based out of Washington, D.C., Shimon was intimately equated with the Bureau and the Giancana case. And as such, he had access to some very sensitive information.

According to Shimon, the meeting between Robert Kennedy and Hoover really did take place. But it wasn’t the revelation that Sinatra was linked with the mob that unsettled the President’s brother. Rather it was the content of some of the F.B.I.’s evidence that spooked him – specifically a recorded conversation between Sinatra and Giancana.

Obtained via a tapped telephone, the recording captured Giancana laying into the singer over the issue of government relief. It seems that the alleged favors the crime lord made for Kennedy’s campaign hadn’t been properly repaid. Now he wanted Sinatra to make good on his friendship with the President and get Kennedy to send him some money.

With his back against the wall, Sinatra began assuring the gangster that he was doing all he could. And to butter Giancana up, the star let him in on his ace in the hole. As Sinatra explained, he was sure to get the relief because the singer was having an affair with someone deep within Kennedy’s inner circle: Pat Kennedy Lawford.

That’s right – Sinatra, by his own reported account, was sleeping with the President’s sister. Moreover, the star made it sound like this liaison wasn’t for fun, but rather a ploy to get everything he could from the Kennedys. “[He] made it sound like quite a sacrifice,” wrote Server quoting Shimon. “He vowed he would, ‘sleep with [Pat] until I get something going.’”

And that, as they say, was that. As Shimon continued, “The tapes were played to Bobby, and Bobby went, ‘WHOA…’” Immediately, the Attorney General ran to his brother and told him of this explosive revelation. “And overnight you saw Sinatra out,” Shimon added. “No more White House. No nothing. Shut him off.”

Without a second thought, the Kennedy clan cut Sinatra from their lives. But somebody had to pass the message on. Clearly, both Kennedy brothers were too furious to tell their pal that he could no longer fraternize with them. So they left that job to their brother-in-law and Lawford, whose breaking of the news clearly didn’t go down well with his Rat Pack costar.

At the time of Lawford’s visit, Sinatra was expecting Kennedy at his Palm Springs estate. The singer had even had a helipad installed in preparation of the politician’s touchdown in Marine One. When Lawford arrived instead, Sinatra was lost for words. Reportedly, the star flew into a rage that resulted in some hefty property damage and Lawford’s ejection from the Rat Pack.

If Sinatra was hurt by this rejection, then it’s possible that it may have influenced his politics in later life. Although a lifelong Democrat, the singer began swinging to the right when he endorsed Republican Ronald Reagan for governor of California in 1970. Later on, he’d offer his services to Richard Nixon and again to Reagan during their respective presidential campaigns.

But in spite of his break with the Kennedy boys, Sinatra maintained friendly relationships with other members of the family. In 1975 the crooner was spotted having dinner with Jackie – a meeting that may have been more than platonic. According to his friend Jim Whiting, Sinatra claimed that the former First Lady had accompanied him to his hotel room afterwards.

And while their intrusive surveillance arguably helped end his relationship with the Kennedys, Sinatra found the F.B.I. an unlikely ally a few years down the line. In 1963 his son Frank, Jr. was kidnapped, forcing the singer to turn to the bureau for help. Not only did agents recover the snatched boy, but they also apprehended the men responsible for the crime.

As time went on, Sinatra and the F.B.I.’s relationship improved significantly. It even got to the point where the star was able to gain access to his own file in 1979 and 1980. Thanks to the Freedom of Information Act, Sinatra could see for himself what the bureau’s beef with him actually was. Incredibly, it all started with a crank letter comparing the crooner to Adolf Hitler.

Sadly, Sinatra was unable to rekindle his relationship with Kennedy in the same way. But it seems that if the star had any ill feelings towards the president, they didn’t last long. During a meeting with Bill Clinton later in life, the star apparently spoke with great fondness about Kennedy. All in all, it seems likely this was a friendship Ol’ Blue Eyes would have given anything to have repaired.