This article originally appeared in the Dallas News written by Anna Harwell Celenza. 

Anna Harwell Celenza is the Thomas E. Caestecker Professor of Music at Georgetown University. Her latest book, Jazz Italian Style: From its Origins in New Orleans to Fascist Italy and Sinatra, hits bookstores in March 2017. Reach her through her website,

It’s been 100 years since Frank Sinatra was born, and there’s a lot of talk lately about his work as a performer. I get that, having first learned about music’s transformative power by listening as a child to my grandfather’s 78s of Sinatra singing with the Harry James Orchestra.


But there’s a whole other side — a political side — to Sinatra. Recently, I learned a little something about American politics by researching what Ol’ Blue Eyes was up to when he wasn’t on stage. Some of today’s politicians could take notes, too.

 Lesson 1: Communism wasn’t always a dirty word

During his formative years, Sinatra was deeply engaged in local politics, thanks to his mother, Dolly, who served as a ward boss for the Democratic Party in Hoboken, N.J. Dolly wasn’t a communist, but like many Americans at the time, she saw the Communist Party as an anti-Fascist force for good. The Communists supported workers’ rights by creating industrial labor unions. They fought against bigotry and racial segregation. Sinatra took these efforts to heart, and eventually became associated with the Popular Front, a coalition of left-wing groups. Sinatra raised money and gave speeches at schools across America, but his greatest contribution to the cause was his starring role in The House I Live In (1945), a 10-minute short film that denounced anti-Semitism while praising a pluralistic America. Sinatra received a special Oscar for his performance, but he didn’t make any money. He donated all his royalties to the California Labor School in San Francisco.

Lesson 2: Overcoming failure is a key to American success

Sinatra’s career fell apart after the war. His tumultuous affair with Ava Gardner ended his marriage with his high school sweetheart, Nancy. And the FBI began to investigate the singer’s possible links to the Communist Party and organized crime. The final blow came in 1952, when a vocal cord hemorrhage all but ended his career. For all these reasons, the press turned on him, sounding the death knell for his career. But Sinatra fought back. In 1953 he won an Oscar for his role in From Here to Eternity and revived his singing career by joining forces with Nelson Riddle. As Sinatra explained in his song That’s Life: “Each time I find myself flat on my face/ I pick myself up and get back in the race.”

Lesson 3: Stay true to yourself, but know your audience

Politicians could learn a lot from listening to Sinatra sing. One of the keys to his success was his willingness to evolve. During World War II, when Sinatra sang songs like All or Nothing at All to crowds of swooning bobbysoxers, he served as a proxy for all the young men at war. When those men came home, Sinatra appealed to them with the same song. He transformed what had been an uplifting declaration of love in 1939 into a melancholy anthem of unswerving masculinity in 1962. As Sinatra himself once said: “When I sing, I believe. I’m honest.”

Lesson 4: Politics is personal

Sinatra never lost his interest in politics. He campaigned for Franklin Roosevelt, Harry Truman and Adlai Stevenson. When John F. Kennedy ran for president, Sinatra became an avid supporter: He raised money for Kennedy and produced his Inaugural Gala. But in 1962, when rumors of Sinatra’s mafia links resurfaced, members of the Kennedy family distanced themselves, and Sinatra took it personally. This was the beginning of his drift to the right. Nixon actively sought Sinatra’s support in 1972, and he was the first to invite Sinatra to sing at the White House. But Ronald Reagan facilitated the real turning point in Sinatra’s political viewpoint. Sinatra and Reagan understood each other: Both were actors, and until 1968, both had been Democrats. They became such close friends that Reagan roasted Sinatra on the Dean Martin Celebrity Roast in 1978, and Sinatra returned the favor by campaigning for Reagan in 1980. “Reagan is the proper man to be the president of the United States,” said Sinatra. “It’s so screwed up now, we need someone to straighten it out.”

Lesson 5: If you’re truly engaged in the world, your opinions will likely change over time

Sinatra went from being a New-Deal Democrat in the 1930s to a Reagan Republican a half-century later. With all the centenary celebrations, there hasn’t been much talk of Sinatra’s political activism. But I think there’s still a lot we could learn from him. Over the course of his life, Sinatra’s political point of view changed in response to current events, and I think this was one of his strengths. If he were alive today, pundits would call him a flip-flopper. That’s the problem with political discourse today: we’re no longer allowed to change our minds. We’re expected to take a side and stick with it. Sinatra paid attention to the world around him, and as it changed, he changed too. That’s what made him great. He did it his way.

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