Political life of Frank Sinatra

Frank Sinatra
Sinatra in 1957
Born	Francis Albert Sinatra (1915-12-12)December 12, 1915 Hoboken, New Jersey, U.S.
Died	May 14, 1998(1998-05-14) (aged 82) Los Angeles, California, U.S.
Occupation	Singer • actor • producer • political activist
Known for	Pioneering civil rights advocacy • passionate Zionism • campaigning for FDR, Truman, JFK, Nixon, Reagan • party switch from liberal Democrat to conservative Republican
Political party	Democratic (Democratic until 1970) • Republican (1970–1998)
Spouse	Nancy Barbato (1939–1951) Ava Gardner (1951–1957) Mia Farrow (1966–1968) Barbara Marx (1976–1998)
Children	Nancy • Frank Jr. • Tina

Frank Sinatra was an American singer, actor, producer, and one of the most influential entertainers of the 20th-century popular culture. Over six decades he was also a major figure in American political life, evolving from a fiery New Deal liberal, civil-rights crusader, and staunch Democrat who campaigned for Roosevelt, Truman, Stevenson, and Kennedy into a conservative Republican who raised millions for Nixon and Reagan and received the Presidential Medal of Freedom from the latter. Shaped by childhood experiences of anti-Italian prejudice, a Jewish neighbor who became his “second mother,” and his mother Dolly’s Democratic machine politics in Hoboken, Sinatra became an early and uncompromising opponent of racism and anti-Semitism. He refused to play segregated venues, forced the desegregation of Nevada casinos, financially supported Martin Luther King Jr., won an honorary Oscar for the anti-racist short film The House I Live In, and was described by contemporaries as the most effective white celebrity in the fight against racial prejudice. Sinatra was a lifelong Zionist who smuggled money for arms to the Haganah in 1948, performed multiple sold-out concert tours in Israel, founded Arab-Jewish youth centers in Nazareth and at Hebrew University, donated entire film salaries to Israeli causes, and maintained his passionate support even after his conservative turn. His political journey was marked by personal humiliation (the 1962 Kennedy Palm Springs snub), alleged Mafia associations that cost him friendships and a gaming license, FBI surveillance for both left-wing and mob ties, and a growing conviction that the Democratic Party had abandoned traditional American values for radicalism on crime, welfare, and foreign policy. Sinatra’s endorsements, inaugural galas, fundraisers, and direct access to the White House made him arguably the most politically powerful entertainer in American history. His trajectory—from ardent 1940s progressive to 1980s Reagan Republican—mirrored and in some ways prefigured America’s own ideological realignment.

Early life and formative influences

Francis Albert Sinatra was born in a cold-water flat in Hoboken, New Jersey, to Italian immigrants Antonino Martino “Marty” Sinatra and Natalina “Dolly” Garaventa. Dolly was a midwife, backroom abortionist, and formidable Democratic ward leader who delivered coal, jobs, and favors in exchange for votes and was arrested multiple times. ^[1] She dominated local politics and taught her son the mechanics of power and loyalty to the underdog. Growing up in a tough Italian neighborhood, Sinatra endured constant ethnic slurs (“wop,” “dago,” “guinea”) that left him with a permanent hatred of bigotry. ^[2] A Yiddish-speaking Jewish babysitter, Mrs. Sarah Golden, spoke only Yiddish to him, gave him a mezuzah he wore for decades, and became his “Jewish mother.” ^[3] He later joked he knew more Yiddish than Italian and called himself “an honorary Jew” or “King of the Jews.” ^[3] These experiences forged Sinatra’s lifelong identification with minorities and outsiders.

1940s: New Deal progressive and anti-racism pioneer

Sinatra credited Roosevelt’s fireside chats with saving America and wrote the president an admiring letter. On September 28, 1944, he was invited to the White House and agreed to help Democratic voter drives. ^[1] He donated $7,500 (≈$130,000 in 2025 dollars), recorded radio spots, spoke at Carnegie Hall and Madison Square Garden, and declared Roosevelt “the greatest guy alive today.” ^[4] In 1945 he starred in the RKO short The House I Live In , interrupting a gang harassing a Jewish boy to preach tolerance: “Look, fellas, religion makes no difference except to a Nazi or somebody as stupid… Don’t let them make suckers out of you.” ^[1] The film won an honorary Academy Award in 1946; Sinatra prized this Oscar above all others. ^[1] That same year, invited by Gary, Indiana’s mayor, he addressed striking white students opposing integration at Froebel High School, comparing their actions to Nazism and earning accusations of communism (which he denied with humor). ^[5] He published an open letter to Henry A. Wallace in The New Republic (January 6, 1947) praising Wallace’s progressive vision. ^[1]

1950s–1960s: Rat Pack, Kennedy glory and betrayal

Sinatra campaigned for Truman (1948) and Stevenson (1952, 1956). In 1960 he became John F. Kennedy’s closest celebrity ally. The Rat Pack toured for JFK; Sinatra rewrote “High Hopes,” commissioned Sammy Cahn lyrics, and produced the legendary January 19, 1961 Inaugural Gala that raised millions. ^[6] Persistent allegations claim Sinatra served as go-between for JFK and Sam Giancana to secure West Virginia and Illinois votes. ^[7] In March 1962, under RFK’s anti-mob pressure, Kennedy canceled a Palm Springs stay at Sinatra had lavishly prepared (new heliport, guest houses) and stayed with Bing Crosby instead. Sinatra was devastated, destroyed the heliport with a sledgehammer, and never forgave RFK. ^[8]

Civil rights activism

From the 1940s Sinatra refused to perform for segregated audiences. In Las Vegas he forced the Sands to serve Nat King Cole in the dining room and, with Sammy Davis Jr., ended Jim Crow policies in Nevada hotels and casinos by 1961. ^[9] He headlined Carnegie Hall for Martin Luther King Jr. in 1961, led Rat Pack boycotts, donated heavily to SCLC and voter registration, and was praised by Vice President Humphrey after the Watts riots for teaching tolerance. ^[1] Orson Welles witnessed Sinatra physically threaten a restaurant owner who refused service to a Black musician. ^[10]

Lifelong Zionism and support for Israel

In 1947 Sinatra headlined “Action for Palestine” at the Hollywood Bowl. ^[3] In 1948, at Teddy Kollek’s request, he smuggled $1 million cash in a paper bag onto a New York ship for Haganah arms purchases, later explaining: “I wanted to help, I was afraid they might fall down.” ^[3] Arab countries banned his music for decades. In 1962 he gave seven sold-out Independence Day concerts in Israel, met Ben-Gurion and Dayan, visited Yad Vashem (declaring Israel “a wonderful country worth dying for”), and used proceeds to found the Frank Sinatra International Youth Center in Nazareth for Arab and Jewish children. ^[3] He returned repeatedly, donated his entire fee from Cast a Giant Shadow (1965), raised $1 million for the Hebrew University student center (opened 1978; bombed by Hamas 2002), and performed benefits for Israel Bonds and the Simon Wiesenthal Center. ^[3]

Party switch and Republican years

By 1969 Sinatra befriended Spiro Agnew. In 1970 he endorsed Ronald Reagan’s California re-election. In July 1972, rejecting McGovern’s “radical” platform, he switched parties and backed Nixon, telling daughter Tina: “The older you get, the more conservative you get.” In 1980 he raised millions for Reagan and produced his inaugural gala. In 1984 he hosted Reagan in Hoboken. Reagan awarded him the Presidential Medal of Freedom in 1985.

Organized crime allegations and political consequences

The FBI’s 2,400-page file documented friendships with Giancana, the Fischettis, and others. Sinatra hosted Giancana at Cal-Neva 1963, lost his gaming license, and was repeatedly denied ties under oath. ^[7] The allegations destroyed his Kennedy relationship, triggered the Palm Springs snub, and made him politically radioactive to Democrats while later Republican administrations embraced him.

References

1. "Frank Sinatra's Pride, Passion and Politics". Brooklyn Jewish Historical Initiative. June 5, 2022.
2. Kelley, Kitty (1986). His Way. p. 544.
3. "'Mr. Sinatra Adored Israel, and Israel Adored Him Back'". Tablet Magazine. May 14, 2015.
4. Summers, Anthony; Swan, Robbyn (2005). Sinatra: The Life. Knopf.
5. Kelley, Kitty (1986). His Way. pp. 120–123.
6. "Frank Sinatra and Politics". Sinatra.com.
7. "Frank Sinatra's Mob Ties and Other Secrets from His FBI File". History.com. May 14, 2018.
8. Kelley, Kitty (1986). His Way. pp. 313–337.
9. Land, Barbara; Land, Myrick (2004). A Short History of Las Vegas. p. 148.
10. Summers, Anthony; Swan, Robbyn (2005). Sinatra: The Life. p. 139.

Bibliography

Summers, Anthony; Swan, Robbyn (2005). Sinatra: The Life. Knopf. ISBN   978-0-375-41400-8.Kelley, Kitty (1986). His Way: The Unauthorized Biography of Frank Sinatra. Bantam. ISBN   978-0-553-26515-6.Kaplan, James (2015). Sinatra: The Chairman. Doubleday. ISBN   978-0-385-53539-7.Santopietro, Tom (2008). Sinatra in Hollywood. St. Martin's.Freedland, Michael (1997). All the Way: A Biography of Frank Sinatra. St. Martin's Press.Taraborrelli, J. Randy (1997). Sinatra: Behind the Legend. Birch Lane Press.