Sinatra, From Kennedy Man to Reaganite

Sinatra: All or Nothing at All, Alex Gibney’s four-hour, two-part documentary wrapping up Monday night on HBO, delves into Frank Sinatra’s life, passions, and musical and movie career.

The film also touches on his role as a major-league political fundraiser and serious campaigner. Despite brushing off early fears he could hurt his singing career with his politics, he later ended up becoming a political liability for two presidents.

Sinatra’s mother, Dolly, was active in Democratic politics in Hoboken, New Jersey, when he was growing up, and her influence on him was clear. He would go on to campaign across the country for Franklin Roosevelt, Harry Truman, and Adlai Stevenson. “[President Roosevelt is] the greatest guy alive today, and here’s this little guy from Hoboken shaking his hand,” Sinatra noted after the president invited him over to the White House for tea. On the campaign trail, Sinatra sang songs and delivered speeches for FDR.

“Some people tell me I may hurt my career by taking sides in a political campaign,” he told a crowd of Roosevelt-Truman supporters at Madison Square Garden a few days before the 1944 election. “And I say to them, ‘To hell with this career. Government is more important.’”

But the politician who Sinatra ended up idolizing most fervently was, without a doubt, John F. Kennedy. Both men were handsome, magnetic forces. Both were avid partiers and womanizers, and they shared similar takes on liberal politics. It didn’t take long for the pair to strike up a friendship. Here’s footage of Kennedy visiting the set of the original, Rat Pack-starring Ocean’s 11 Las Vegas:

“His love for Kennedy was so strong,” Nancy Sinatra wrote of her father. “JFK was his friend. For the patriotic American dreamer, this was the ultimate compliment: The President of the United States was his friend.”

During the 1960 presidential campaign, Sinatra was an effective fundraiser and campaigner for JFK, and he went on to produce and star in the Inaugural Gala.

“The main thing to know about Sinatra, and the reason he campaigned so hard for Jack Kennedy, is that Sinatra was addicted to power,” author James Kaplan—the second volume of whose Sinatra biography, Sinatra: The Chairman, is set for release in October—told The Daily Beast. “And Washington power was an especially heady version of the power he was addicted to. There’s something about Washington and being connected to leaders of the Western world that very much appealed to him.”

Although Sinatra committed decades to liberal causes and the Democratic Party, the remainder of the ’60s laid the groundwork for his defection to the Republican Party and his later status as a full-blown celebrity Reaganite.

“For Sinatra, it wasn’t like the other Reagan Democrats,” Kaplan said. “It had a particularly Sinatra-esque tinge to it.”

In the spring of 1962, President Kennedy had planned on staying the weekend at Sinatra’s Palm Springs residence. Sinatra had spent a lot of time and money renovating his home to make it look more presidential. But shortly before the visit, Kennedy’s brother Bobby intervened: Sinatra’s ties to, and friendly relationships with, mob bosses such as Sam Giancana were too much of a political liability. So the president stayed at rival singer Bing Crosby’s place instead.

The snub absolutely infuriated Sinatra, who reportedly picked up a sledgehammer upon hearing the bad news and started destroying the heliport he had installed for the president’s big arrival. “The fuse for Sinatra’s nitroglycerine was always humiliation [and] losing face,” Kaplan said.

After he failed to strike up anything close to a rapport with Democratic presidential nominee Hubert Humphrey and President Lyndon Johnson, Sinatra’s drift to the right gained more momentum. In 1970, he made the surprise announcement that he was backing Ronald Reagan for governor of California. (Sinatra had previously been consistently vocal about his disdain for both Ronald and Nancy Reagan.) Sinatra even warmed up to the Nixon White House.

“I think that 1970 was such a heavy year, with the Kent State killings, all the protests on college campuses—Sinatra was really freaked out with all the disorder in the country, and that helped push him to the right,” Kaplan said.

Sinatra and Reagan grew chummy enough that Reagan roasted the singer on The Dean Martin Celebrity Roast in 1978, just a couple years before his successful presidential run.

“Frank Sinatra would make a president who is strong on defense, but again, will have concern for humanity,” Reagan joked. “Scientists at his urging have developed an intercontinental ballistics missile that is not a weapon of mass destruction. It only hits photographers.”

And when the Reagan era—and the conservative revival that came with it—kicked into full swing, Sinatra once again had a dear friend in the Oval Office. “The liberal approach didn’t work as well as it should have, and I think maybe a lot of us have moved away from it,” Sinatra said, after explaining he was a “very big” fan of his “old friend” Ronald Reagan, at the 1980 Republican National Convention.

Shortly after Reagan defeated Carter, the president-elect announced that Sinatra had been chosen as director of entertainment for the Inaugural Gala for the first time since Kennedy’s inaugural celebration. Throughout the Reagan years, Sinatra remained a reliable supporter and Republican fundraiser. (He also became something of a political liability to Reagan, as well, albeit to a much lesser extent than with Kennedy, though the subject matter should seem familiar.)

Throughout Sinatra’s political evolution, he was consistently unapologetic and ardent in his approach. Even when he wasn’t trying to do so, he could affect the calculations of major political figures—even those outside the United States. In late 1989, as the Cold War was winding down, the Soviet Union’s spin doctors were, apparently, attempting to appeal to Western culture and sensibilities. A top Foreign Ministry spokesman announced that the Kremlin had started operating under what it termed the ”Frank Sinatra Doctrine” in Eastern Europe—meaning the USSR would allow the Soviet republics to do things “their way” as the empire dissolved.