I remember Sinatra who didn’t pal around with rich Republicans. During the early 1950s, at my Sunday school in St. Paul, Minnesota, one of the highlights of the year was the annual screening of The House I Live In, a short film starring a young and skinny Sinatra. In it, he told a gang of kids that racial and religious differences “make no difference except to a Nazi or somebody who’s stupid.” He sang about “The people that I work with / The workers that I meet. . . . The right to speak my mind out / That’s America to me.” The House I Live In, made at the peak of Sinatra’s popularity, won him a special Academy Award in 1945. Four years later his career was in ruins, in the wake of charges that he was tied to both the Mafia and the Communists. Forty years later his career is legend, his politics solidly conservative.

At first glance Sinatra’s political Odyssey from left to right seems to have followed a well-trod path. “Maturity” has been defined by figures as different as John dos Passos and Jerry Rubin as the abandonment of youthful ideals. But Sinatra’s case is different. Beaten down as an activist leftist, his career destroyed by the right-wing press, he made a stunning comeback, then found himself snubbed and abused by the liberals whose views he shared. Only then did he sign up with his old right-wing enemies.

The House I Live In was a turning point. The Cumulative Index to Publications of the Committee on Un-American Activities (HUAC), a handy list of everyone named as a communist in 20 years of committee hearings, indicates that in the eight years following The House I Live In Sinatra was named 12 times. The New York Times Index for 1949 contains a single stunning cross-reference: “Sinatra, Frank: See US—Espionage.” Sinatra reportedly denied the reports that he “followed or appeased some of the CP [Communist Party] line program over a long period of time.”

But once the allegations had been made, Sinatra’s image in the press changed dramatically. He was first linked to the Mafia in a February 1947 gossip column that reported he had been seen in Havana with mobster Lucky Luciano and other “scum” and “goons” who “find the south salubrious in the winter, or grand-jury time.” The columnist’s source, and the source of many subsequent Mafia-Sinatra stories, turns out to have been Harry Anslinger, a crony of J. Edgar Hoover. Anslinger served as head of the federal narcotics bureau and was out to get Sinatra because he was a “pink.”

“Frank’s big nosedive,” as the pundits called it, began on April 8, 1947. That was the night he punched Hearst gossip columnist Lee Mortimer at Ciro’s celebrated Hollywood night spot. The Hearst papers went wild, running whole pages on the incident, repeating the Mafia story and HUAC charges. “Sinatra Faces Probe on Red Ties,” a headline read. Soon gossip titans Hedda Hopper, Louella Parsons, and Dorothy Kilgallen were heaping abuse on him. Overnight Sinatra was transformed by the right-wing press from the crooning idol of bobby-soxers into a violent, left-wing Mafioso.

Sinatra said he punched Mortimer because the columnist called him a “dago.” In fact Mortimer had been calling him some other things in print. He wrote about what he called “the crooner’s penchant for veering to portside” and reminded readers that Sinatra had been named in HUAC testimony as “one of Hollywood’s leading travelers on the road of Red Fascism.” Mortimer, nephew of the editor of the Hearst-owned New York Mirror, pledged that “this column will continue to fight the promotion of class struggle or foreign isms posing as entertainment”–like The House I Live In.


How pink had Sinatra been? HUAC’s sources were pretty disreputable. The first to name him was Gerald L. K. Smith, a raucous native fascist. In 1946 he told the committee that Sinatra “has been doing some pretty clever stuff for the Reds.” Sinatra was named again in HUAC testimony in 1947 by Walter S. Steele, a private Red-hunter who had once accused Campfire Girls of being “Communistic.” Jack B. Tenney, a California state senator who headed a state version of HUAC, reported in 1947 that Sinatra had taken part in a dinner sponsored by American Youth for Democracy, which J. Edgar Hoover had declared a communist front.

Between The House I Live In in 1945 and the big 1947 HUAC hearings, Sinatra had in fact moved much closer to organized left-wing political activity. In 1943, when riots broke out in Harlem, he went uptown to speak at two integrated high school assemblies, urging the kids to “act as neighborhood emissaries of racial goodwill toward younger pupils and among friends.” Shortly after, when white students in Gary, Indiana, boycotted classes at their newly integrated high school, Sinatra spoke in the school auditorium and sang “The House I Live In” What other star at the top of the charts has thrown himself into the civil rights struggle so directly?

In May 1946 Sinatra issued what Billboard called “an anti-Franco blast.” The statement was remarkable for two reasons. First, the only people who still remembered the support that Spain’s dictator received from Hitler and Mussolini were real leftists. And second, there was Sinatra’s Catholic background. The comment caused the Catholic Standard and Times of Philadelphia to label him a “pawn of fellow-travellers.”

Sinatra moved closer to the Communist Party in July 1946, when he served as vice president of the Hollywood Independent Citizens Committee of the Arts, Sciences and Professions. Known by its asthmatic acronym, HICCASP had been a broad coalition of pro-Roosevelt liberals and leftists, ranging from Thomas Mann to Rita Hayworth. Sinatra became an officer during a faction fight in which Communists pushed liberals out of the organization and steered it toward Henry Wallace’s leff-wing challenge to Truman in 1948. Sinatra wrote an open letter in the New Republic to Wallace at the beginning of 1947, calling on him to “take up the fight we like to think of as ours—the fight for tolerance, which is the basis of any fight for peace.” Within three months headlines appeared linking him to the Communists.

A month later he was fired from his radio show; six months after that his New York concerts flopped. Soon his personal life was falling apart as fast as his career. By December 1949 his affair with Ava Gardner had become an open scandal. Columbia Records was trying to get back the advance they had given him. In 1950 he was released from his MGM film contract, and his own agent, MCA, dropped him. He was a has-been at 34.

After Sinatra’s stunning 1953 comeback in From Here to Eternity, he remained a Democrat. He sang “The House I Live In” at the Hollywood Palladium at a 1956 campaign salute to Adlai Stevenson. He returned to the political wars with new energy during the spring of 1960. He had two projects that season: working for the Kennedy campaign (Sinatra’s version of “High Hopes” was the official Kennedy campaign song) and breaking the Hollywood blacklist that had barred left-wingers from working in the movies ever since the 1947 HUAC investigations.

The second project was announced shortly after Kennedy won the New Hampshire primary. The New York Times headline read, “Sinatra Defies Writer Blacklist / Hires Albert Maltz for his job filming of ‘The Execution O’ Private Slovik.’” Maltz had written The House I Live In. In Execution of Private Slovik, a recently published novel, told the story of the World War II G.I. who became the only American since the Civil War to be executed for desertion. “This marks the first time that a top movie star has defied the rule laid down by the major movies studios” 13 years earlier, the Times explained. Sinatra would produce, Robert Parish was to direct. Slovik would be played by a TV tough guy named Steve McQueen.


Sinatra, asked if he was fearful of the reaction to hiring a blacklisted writer, had a defiant, I-told-you-so response. He quoted his own 1947 statement criticizing HUAC’s witch-hunt: “Once they get the movies throttled, how long will it be before the committee gets to work on freedom of the air? . . . If you make a pitch on a nationwide radio network for a square deal for the underdog, will they call you a commie?”

A square deal for the underdog seemed to be exactly what Sinatra was after—for underdog Maltz, who served time in a federal penitentiary for refusing to name names, and also for Slovik. According to director Parish, Sinatra regarded Slovik not just as a victim of an unjust system of military justice, but as “the champ underdog of all time.”

“They’re calling you a fucking Communist!” Harry Cohn, king of Paramount Pictures, shouted at Sinatra. The attack had come, predictably, from Sinatra’s old enemies in the Hearst press. Editorial writers for the New York Mirror reminded readers that the guy who just hired a Red had once had a “‘romance’ with a dame to whom he was not then married.” (Sinatra must have murmured, “Hey, that was no dame, that was Ava Gardner!”)

John Wayne found Sinatra’s Achilles’ heel. Asked for his opinion on Sinatra’s hiring of Maltz, Duke said, “I don’t think my opinion is too important. Why don’t you ask Sinatra’s crony, who’s going to run our country for the next few years, what he thinks of it?” Sinatra responded with “A Statement of Fact,” for which he bought space in the New York Times. In it, he declared that connecting candidate Kennedy to his decision to hire Maltz was “hitting below the belt. I make movies. I do not ask the advice of Sen. Kennedy on whom I should hire. . . . I have, in my opinion, hired the best man for the job.”

Just as the controversy seemed to be dying down, the Hearst papers ran the banner headline: “Sinatra Fires Maltz.” The Times and the trades contained a new ad signed by Sinatra, headlined simply “Statement”: “Mr. Maltz had ... an affirmative, pro-American approach to the story. But the American public has indicated it feels the morality of hiring Albert Maltz is the more crucial matter, and I will accept this majority opinion.”


In an interview shortly before his death in 1985, Maltz recalled the incident. “Sinatra threw down the gauntlet against the blacklist,” he said. “He was prepared to fight. His eyes were open. The ad firing me was ridiculous. The American people had not spoken; only the Hearst press and the American Legion had. Something had come from behind that caused him to change his position.”

Maltz brought out his scrapbooks. Among hundreds of faded clippings was one from Dorothy Kilgallen’s gossip column. “The real credit belongs to former Ambassador Joseph P Kennedy,” she wrote. “Unquestionably anti-communist, Dad Kennedy would have invited Frank to jump off the Jack Kennedy presidential bandwagon if he hadn’t unloaded Mr. Maltz.” Kennedy’s campaign advisers worried also about Sinatra’s Mafia aura and expressed the hope that the singer would keep his distance from the senator. But, the advisers said, they hoped Sinatra would help with a voter drive in Harlem, “where he is recognized as a hero of the cause of the Negro.”

After the election, JFK asked Sinatra to organize and star in his inaugural gala. The singer proudly escorted Jackie, but Jack was the one he cared about. In a gesture of classic macho deference, Sinatra offered to share a prize girlfriend, Judith Campbell Exner, with the president. Kennedy liked the idea and began an affair with Exner. (Sinatra’s hit that year, appropriately enough, was All the Way.) Then Sinatra Went too far; he introduced Exner to Chicago Mob leader Sam Giancana.

J. Edgar Hoover’s ever-present eyes and ears quickly discovered the liaisons. Bobby Kennedy, in the middle of a campaign to crush the Mafia, put a stop to his brother’s involvement with Exner. The Kennedys had been planning to stay with Sinatra in Palm Springs. He’d remodeled his house in anticipation of the presidential visit. At the last minute, JFK announced they’d stay instead with Bing Crosby—who wasn’t even a Democrat. To the public, it was an inexplicable snub.

Sinatra always was, as Village Voice jazz critic Gary Giddins puts it, “a virtuoso at storing wounds.” He got even with Bobby in the 1968 California primary by supporting Humphrey. Then he discovered the Humphrey campaign had the same reservations that the Kennedy campaign had had, and he quietly left.

As youth culture flowered in 1966, Sinatra married Mia Farrow; he’d just finished an album he called September of My Years. He was 51, she was 21, five years younger than his daughter Nancy. A sixties rebel, Mia cut her hair short and wore pants, and opposed the Vietnam War. Sinatra’s friends explained the attraction: “He digs her brain.” Soon, however, she was denouncing him and his pals: “All they know how to do is tell dirty stories, break furniture, pinch waitresses’ asses and bet on the horses,” she said. She left him to join the Beatles in India, meditating with the Maharishi.


Sinatra announced his retirement in 1971. “The principle activity of his retirement years,” New York Times music critic John Rockwell writes, “was his political shift from left to right.” The key moment seems to have come when the House crime committee held a new investigation of Sinatra’s Mob ties in 1972. The committee was headed by Democrats including California senator John Tunney, an old Kennedy friend for whom Sinatra had raised $160,000 with a special show. The main evidence against him was the testimony of a confessed hit man who said that a New England Mafia boss had boasted that Sinatra was “fronting” for him as part owner to two resort hotels. The committee called Sinatra. “That’s all hearsay evidence, isn’t it?” Sinatra asked. “Yes, it is,” the committee counsel admitted.

Always a public man, Sinatra explained the shift in his political thinking in a New York Times Op-Ed piece he wrote just after he appeared before the committee. His old politics of standing up for the little guy had been altered. Now he embraced the right-wing populism that defined the principal oppressor of the little guy as big government. And he saw his subpoena as a prime example of government oppressing a little guy. Sinatra became a Reagan Republican. “It didn’t gall him as much as he had thought it would,” reported columnist Earl Wilson.

His turn to the right coincided with a deepened contempt for women and his most offensive public behavior ever. At a pre-inaugural party in 1973, he shouted at Washington Post columnist Maxine Cheshire, “Get away from me, you scum. Go home and take a bath. . . . You’re nothing but a two-dollar cunt. You know what that means, don’t you? You’ve been laying down for two dollars all your life.” He then stuffed two dollar bills in her drink, saying, “Here’s two dollars, baby, that’s what you’re used to.” He made that kind of language part of his concert routine for several months, to the evident enjoyment of his new right-wing following.

President Nixon invited him to perform in the White House in 1973—something the Democrats had never done. He sand “The House I Live In.” Twenty-eight years earlier, he had sung it for students at newly integrated high schools. Now he was singing for the man who began his career as a member of HUAC from 1946 to 1950, when the committee smeared Sinatra. The president beamed with satisfaction, and Pat Nixon kept time by nodding her head. At the end of the program, for the first time in his public career, Sinatra was in tears.