Skip to content
The logo for Brooklyn Jewish Heritage Initiative whose mission is to Organize Public Events, Create Oral & Video Histories, Provide Resources to the Brooklyn Jewish Community

Brooklyn Jewish
Historical Initiative

bc Home » Frank Sinatra’s Pride, Passion and Politics

Frank Sinatra’s Pride, Passion and Politics

  • by

By Joe Dorinson

Our house, the Bible teaches, is one of many mansions. Frank Sinatra whose 100th birthday we celebrate this Saturday, December 12, 2015 began his great ascent to the room at the top in 1935 when he broke into show business on Major Bowes’s Amateur Hour. His rise, over Judy Garland’s rainbow, personifies the American Dream. His achievements have earned this self-styled saloon singer a permanent perch among the icons in our pantheon. Most studies of Sinatra, however, pay little attention to his politics; hence this effort to shed some light on a neglected but important subject.

Sinatra’s political education started at home in Hoboken, New Jersey where his mother, Dolly Graventi Sinatra functioned as a ward-heeler. In return for favors extended to recent immigrants who flocked to Hudson County, she garnered votes for the Democratic machine. Realizing that politics is the art of accommodation, Dolly filled a vacuum that our Founding Fathers and their progressive children in rigid deference to their waspish values had created. Thus, when semi-literate indigent newcomers needed coal to heat their cold-water flats, turkeys to feed their hungry children at Thanksgiving or jobs for family survival they turned to the urban bosses. High-minded sentiment and lofty sermons on rugged individualism, moral responsibility and civic duty did not suffice. Following in the wake of Irish politicians, Dolly Sinatra was always there: to help as well as to reap rewards. She got her husband Marty a job in the local fire department and opened a saloon during the era of prohibition. And in 1932, at the height of the Great Depression, she bought a four-story house.

Daughter Nancy describes her father’s political odyssey in a colorful way. Identifying with marginal Americans, Sinatra supported Franklin Delano Roosevelt’s New Deal: actively campaigning for the president in 1944 at considerable risk to his high-flying career. The President took Sinatra (with or without sugar?) to tea on September 28, 1944 at the White House. Invited along with saloon-keeper, Toots Shor and comedian Rags Ragland at the suggestion Democratic National Committee Chair, Bob Hannegan, the crooner sang Roosevelt’s praise: “The greatest guy alive.” Bantering with reporters upon leaving, he endorsed Roosevelt for reelection and joined the campaign.  He spoke at rallies and on radio. When he put his money, $5000 near his mouth so to speak, the kid from Hoboken elicited condemnation from right-wing journalists like Lee Mortimer and Westbrook Pegler.

This acrimonious exchange marked the end of Sinatra’s honeymoon with the press and the beginning of a long feud with the fourth estate. The singer resented the double standard imposed on him. When Ginger Rogers and George Murphy (later elected to the U.S. senate from California) campaigned for Republican candidate, Tom Dewey, no adverse commentary surfaced. To his critics, Sinatra shot back:

My first real criticism came from the press when I campaigned for President Roosevelt in 1944. A few columnists took me to task insisting that entertainers should stick to entertaining. They also realize it is bad public relations to indulge in politics because you may lose fans who don’t agree with you. However, I feel it is the duty of every American citizen to help elect the candidate of his choice.


Frank made his political debut on October 31, 1944 at Madison Square Garden flanking Harry Truman and Fiorello LaGuardia. The rally, sponsored by the Liberal Party (not a dirty word in the halcyon 40s), attracted many famous people. Senator Robert Wagner, Vice-President Henry Wallace, entertainers Ethel Merman, Benay Venuta and Victor Borge drew cheers from 20,000 in attendance. Bill “Bojangles” Robinson, the fabulous Negro dancer, swapped roles with the young singer from Hoboken. Sinatra danced; Robinson sang. Warned that his political activities would hurt his career, Sinatra countered: “Well, the hell with that. I’m more interested in good government than in my own future.” At a loss for words without music, Sinatra appeared emotionally drained. All that the crooner managed to say about FDR was:” He is good for me and my kids and my country.” At subsequent rallies he teamed up with Orson Welles. This dynamic duo excelled on radio. A largely Republican press aimed their barbs at Sinatra. Happily, the nation’s youngsters, “bobbysoxers”, mostly poor, adored “The Voice.” Despite his fragile physique and because of his enormous success, he embodied their quest for power and articulated their need for heroes. Bruce Bliven, from whom this last observation is borrowed, had it right: “Perhaps Frankie is more important as a symbol than most of us are aware.”

After the election, Sinatra embarked on a crusade against intolerance. Mentored by politically liberal George Evans, Sinatra talked to Bronx high school students about juvenile delinquency, a prime concern on the home front during World War II. He received coverage on the front page of The New York Daily News. This led to a nationwide tour of ten cities. Not all newspapers responded favorably. For example, bilious and bibulous Westbrook Pegler of the Hearst Press took potshots at the popular singer.

In 1945, Frank Sinatra garnered laurels for his work against prejudice from the National Conference of Christians and Jews. To promote this worthy cause, producer Frank Ross suggested a film with a song. “Putting his convictions on the line,” writes daughter Nancy Sinatra, “Dad played himself, preaching tolerance to a group of boys in The House I Live In, a 10-minute short for RKO…on the theme of racial tolerance.”

This mini-masterpiece was the product of Lewis Allen, composer Earl Robinson and screenwriter, Albert Maltz. Allen had written the blistering attack on lynching, “Strange Fruit” so hauntingly sung by Billie Holiday. Earl Robinson had teamed up with John Latouche to write a one act oratorio, “Ballad for Americans”, first recorded by Paul Robeson and later, Bing Crosby.

Directed by Mervyn LeRoy, the film was shot in two days in May, 1945, one month after the death of President Roosevelt. Sinatra introduced the song in August, the month of Hiroshima and Nagasaki. Sinatra recorded it with Columbia and featured it on the “Old Gold” show between 1945 and 1947. Both Sinatra and LeRoy received Oscars in 1946 for this film, a powerful and friendly persuader. Later, Sinatra informed Edward R. Murrow in a televised interview that he prized this Oscar more than the one From Here to Eternity.

Note the punch line. “Look, fellas”, Sinatra reasons, “religion makes no difference except to a Nazi or somebody as stupid…Don’t let them make suckers of out of you.” In this remarkable venture, great music resonated with good politics in this apotheosis of post war America when “Our House” began to open its doors to “strangers in the night.”

Sinatra recorded another commentary on racial politics in 1946. Kurt Weill and Maxwell Anderson wrote “Lost in the Stars” three years before the musical drama of the same name reached Broadway. The song exemplifies a progressive social and musical ideology. Drawing on African folklore, it delivers a powerful message in three minutes and thirteen seconds. He practiced what he sang. When Sinatra learned that the Lakeside Country Club had a membership policy which excluded Jews, he followed another gentile member, Darryl Zanuck in joining the Hillcrest Country Club. In another instance, Orson Welles, Frank Sinatra and a Negro driver entered a restaurant. A giant waiter refused to serve the chauffeur. Welles remembered that Sinatra reared up, grabbed the server and insisted: “You’re serving coffee for three.” By “sheer force of character”, Frank triumphed. Each incident, however, drew fire from the conservative press.

Picture, if you will, “Autumn in New York”, 1947. Frank Sinatra encouraged Sammy Davis, Jr. to perform with him at New York’s Capitol Theater. The Hearst Press, biographer John Howlett observes, replaced a favorable review with a hostile one co-authored by Lee Mortimer and Jack Lait. These Hearst hit-men blasted Sinatra’s performance. They gloated when attendance sagged. Eventually, Mortimer would earn a well-aimed sock on the jaw from the explosive singer.

Thanks to the brilliant efforts of my co-panelists, Professors Jon Weiner, Michael Nelson and Dean Leonard Mustazza, I have gained deeper insights into the political Sinatra. I learned, for example, that the Hoboken heart-throb was also a writer. In a series of essays, Sinatra crafted eloquent pleas for ethnic understanding and racial tolerance. As a victim of prejudice during the 1920s and 1930s, he identified with the outsiders: Dostoyevsky’s “insulted and injured.” He urged the young readers to be smarter than his contemporaries. Of particular significance is Sinatra’s open letter to Henry Wallace published in The New Republic on January 6, 1947 but written one month prior. Calling for world peace and the right (inclined to the left) leadership to achieve this goal, Sinatra sang the praises of the former Vice-President and exhorted him to seek the presidency in 1948. Using a star’s “Bully Pulpit” to frame political solutions to political problems, the celebrated crooner created a precedent. And this act of courage coupled with conviction brought “heat” from the house of Hoover. The notorious “Red Hunter” and homophobic closet queen joined forces with the House Un-American Activities Committee to pillory Sinatra as a “Pinko.”

No stranger–night or day–to controversy or confrontation during the “Organization Man” 1950s, Sinatra subverted the cultural code. Though he extolled “Love and Marriage”, he thundered against the “Tender Trap.” He deviated from the sing-along thrust of Mitch Miller. As living standards rose, musical standards declined. Sinatra, Friedwald persuasively argues, maintained high bench-marks in popular song.17 Recruited by friend, Peter Lawford, Sinatra joined the Kennedy bandwagon in 1960. In the struggle for the presidential nomination, daughter Nancy reports that her father secured the support of Sam Giancana in the crucial West Virginia primary. His mother Dolly helped to swing the Hudson County delegation issuing from Jersey City. His hit song, “High Hopes” was altered for and tailored to the Kennedy campaign. Sinatra also commissioned a pro JFK libretto from another buddy, the “Irresponsible” Sammy Cahn. In 1961, this led to the “Old Jack Magic.” Distanced by allegations of Mafia guilt by association, Sinatra remained a Kennedy devotee. He sang melancholy songs following the assassination of both Kennedy brothers in evoking that “brief shining moment.”

According to Alan King, cum comic, actor, producer, friend, the break with the Kennedys was strictly personal. For years, Sinatra had been an ardent Democrat and zealous fundraiser. He orchestrated the entire pre-inaugural gala which featured a true galaxy; among them: Ethel Merman, Nat King Cole, Louis Prima, Helen Traubel, Leonard Bernstein, Frederick March, Anthony Quinn, Bette Davis, Sidney Poitier, Laurence Olivier, flanked by the Mormon Tabernacle Choir and Nelson Riddle’s orchestra. But trouble, like Herbert Hoover’s vaunted prosperity, was just around the corner. When Sinatra invited President Kennedy to stay at his Palm Springs estate, the Chief Executive accepted, gladly. Pressure from the Justice Department, headed by brother Bobby, compelled the captain from Camelot to alter course. At the behest of Hoover and his brother, both concerned with the Sam Giancana-Frank Sinatra mob connection, Kennedy stayed at the estate of Bing Crosby, a registered Republican. A fuming Frank neither forgot nor forgave the Kennedys. King asserts that in his heart Sinatra remained a Democrat.

He also retained his core values. Even when he reinvented his artistry and refashioned his politics, Sinatra remained “a fighter against his times.” As Dr. Mustazza reminds us, he opened doors for black performers: as guests at the Copacabana, the Muse of Barry Manilow, and as entertainers in Las Vegas or “Lost Wages” in the words of Lenny Bruce. Black artists, Nat King Cole and Sammy Davis, Jr. and Black athletes, Joe Louis and Sugar Ray Robinson: all benefited from the saloon singer’s largesse. Sinatra put his money to work in behalf of causes that he voiced. In addition, he performed at benefits for organizations as diverse as the NAACP, the Simon Wiesenthal Center, and SCLC.

At this juncture, the Rat Pack phenomenon deserves attention. This stage in Sinatra’s life has attracted increasing interest punctuated by several films tailored for TV. On the surface, it appears as a case of arrested juvenile development. Certainly, an element of residual adolescence lies at the heart of Sinatra’s capers. But the antics have deeper significance.

The idea started with Humphrey Bogart. At his home in Holmby Hills, California, Bogie and his wife, Lauren Bacall hosted a bunch of hard-drinking non-conformists. In 1955, they headed for Las Vegas to watch Noel Coward at the Desert Inn. With Sinatra, Judy Garland, David Niven, Irving “Swifty” Lazar, Jimmy Van Heusen and Angie Dickinson in tow, they cavorted in Glitz town. When Bacall saw them inebriated in the casino, she remarked: “You look like a goddamn rat pack.”

After Bogie’s death of lung cancer in 1957, Sinatra who had served as “Pack master” assumed leadership. A new court formed around Frank. It included Joey Bishop, Sammy Davis Jr., Dean Martin and Peter Lawford as the core group or two Jews, two Italians, one African-American, and one WASP.

“The Rat Pack show,” writes Max Rudin, “featured–even flaunted–race and ethnicity. Bishop, dressed as a Jewish waiter, warns the two Italians to watch out” for the Matzia, his own group. When John Kennedy took a breather from the presidential race in 1960, Martin picked Davis and offered him to the candidate as an award from the NAACP. The Pack, unlike the silent generations that preceded, paraded their ethnicity. Davis quipped: “I’m colored, Jewish and Puerto Rican. When I move into a neighborhood, I wipe it out.” No longer victims of prejudice, they used humor to lash out at prejudice. And Peter Lawford, the only WASP, (though a convert to Catholicism, a product of a marriage to Kennedy’s sister Pat) became the comic foil. His pompous British persona, shades of Shakespeare’s Falstaff, not Verdi’s, sparked the mirth in others. The butter was transformed into the butt.

In the political arena, throughout the 1960s, Sinatra hated Nixon. He could barely shake his hand at Toots Shor’s in 1962; he campaigned for Pat Brown against Ronald Reagan for governor of California in 1966. He brought fellow rat-packer Dean Martin along for the political ride. After the Watts Riot in Los Angeles in 1965, Vice-President Humphrey praised Sinatra for teaching tolerance and preaching against prejudice among young people. Both promoted a series of concerts to raise money for voter registration drives to implement the Voter Rights Act of 1965.25

Seven years later, he buddied up to Agnew first and Nixon too in 1972 appearing at a White House reception on April 17, 1973. How does one explain this defection? Daughter Tina, a staunch McGovern supporter was appalled reports her sister, Nancy “with the laughing face.”26

Sinatra’s switch to conservative Republican politics is both baffling yet understandable. A self-made man, his great ascent in American popular culture carried him inexorably to the right. Although he supported Pat Brown for re-election as governor of California against the successful challenger, Ronald Reagan in 1966, Sinatra was already “turned off” by the radical politics in the 1960s. A man of deep personal loyalties and visceral dislikes, “Old Blue” eyes followed his impulses. Never a consistent thinker (the “hobgoblin of little minds” re: Emerson) or a political sophisticate, Sinatra enjoyed golfing with Spiro [the zero] Agnew in Palm Springs. This led to the recruitment of disaffected Democrats to the Republican banner in 1972. Ironically, as the Watergate felons were thrust out of office in disgrace, Sinatra remained faithful to his fallen comrades. He also decided to unretire and return to public performance. Admirable moves to be sure; but an incident in 1960 reveals a less noble side to the Sinatra persona.

Albert Maltz, a victim of the “Red Scare” wrote a script “The Execution of Private Slovik” at the behest of Sinatra. The Catholic hierarchy in New York balked at the rehabilitation of this communist writer. Cardinal Spellman communicated his opposition to Joseph Kennedy who feared ugly repercussions on his son’s bid for the presidency. Bowing to pressure, Sinatra sacrificed Maltz on the altar of political expediency.27 It was not his finest hour.

Abruptly, Sinatra moved to the right of the political spectrum. Clearly, he had switched houses. Less obvious are the causes of this departure. A number of Frankophiles have fixed on the Joe Kennedy-orchestrated break because of Sinatra’s alleged mafia links. In various television documentaries which aired following the death of Sinatra, Peter Lawford was cited as both the match-maker and the messenger (of bad tidings) that initially attracted and later repelled, indeed expelled Sinatra from the inner-sanctum. Perhaps. But other, more cogent reasons animated the move.

In a recently published book about black-listed artists, Tender Comrades, Sinatra is singled out for his humane treatment of those who were victimized by the “Red Scare.” Faith Hubley recalls his kindness. She also quotes Lionel Stander, that gravel-voiced, one-eyed character actor, to the effect that he not only read Karl Marx but “Old Blue Eyes” was the only actor who could “comprehend it.”28 Whatever the underlying reasons, Sinatra’s Democratic residence was part of a distant past. Wooed by Agnew, courted by Nixon, seduced by Reagan, the kid from Brooklyn by way of Hoboken climbed luxury’s ladder to embrace fat-cat politicos and conservative leaders as his boon companions. Vintage Sinatra, say around midnight of 1945, had a better voice in this writer’s judgment and, bereft of sour grapes, sounder politics.

Brooklyn’s best writer, Pete Hamill has the last word. Sinatra mattered because he was the first artist/entertainer to get involved, politically, proudly, and passionately.29 Hurt as a little boy by the hate-filled epithets hurled at him, he never forgot. Sinatra signed petitions. Throwing caution to the summer wind, he threw his Jimmy Van Heusen pork-pie hat into the political arena. He supported candidates. He spoke out. A new breed of entertainer, he refused to play the “invisible man” or sit on the humpty-dumpty political fence. Surrounded by hostile children like those in documentary, The House I Live In, that vulnerable boy on the ledge represents the young Frank Sinatra as well as Mike D’Innocenzo, Jon Weiner, Len Mustazza, Joe Dorinson: indeed everyone who was marginalized in America: blacks, Jews, Catholics, immigrants, Hispanics, and gays. Recent biographical studies document the mutual love affair between Sinatra and Israel. He helped the fledgling Jewish state with guns, geldt (money) by association, and vocal support we now know beyond a shadow of a Hitchcock doubt. Happily, we all found a champion in a self-styled saloon singer from New Jersey. Because of his powerful voice, the doors in our nation’s house opened and the walls of bigotry started to crumble. And America–in the eloquent words of poet Langston Hughes– “became America again.” Thank you, Frank Sinatra.