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Political views and activism

Sinatra held varied political views throughout his life. His mother, Dolly, was a Democratic Party ward leader,. After meeting President Franklin D. Roosevelt in 1944, he subsequently heavily campaigned for the Democrats in the 1944 presidential election. According to Jo Carroll Silvers, in his younger years, Sinatra had "ardent liberal" sympathies and was "so concerned about poor people that he was always quoting Henry Wallace." He was outspoken against racism, particularly toward black people and Italians, from a young age. In the early 1950s, he was among those who campaigned to combine the racially segregated musicians' unions in Los Angeles. In November 1945, Sinatra was invited by the mayor of Gary, Indiana, to try to settle a strike by white students of Froebel High School against the "Pro-Negro" policies of the new principal. His comments, while praised by liberal publications, led to accusations by some that he was a communist, which he said were not true. In the 1948 presidential election, Sinatra actively campaigned for President Harry S. Truman. In 1952 and 1956, he campaigned for Adlai Stevenson.

Of all the U.S. presidents he associated with during his career, he was closest to John F. Kennedy. Sinatra often invited Kennedy to Hollywood and Las Vegas, and the two would womanize and enjoy parties together. In January 1961, Sinatra and Peter Lawford organized the Inaugural Gala in Washington, D.C., held on the evening before President Kennedy was sworn into office. After taking office, Kennedy distanced himself from Sinatra due partly to Sinatra's ties with the Mafia. In 1962, Sinatra was snubbed by the President as, during his visit to his Palm Springs, Kennedy stayed with the Republican Bing Crosby instead of Sinatra, citing FBI concerns about the latter's alleged connections to organized crime. Sinatra had spared no expense upgrading the facilities at his home in anticipation of the President's visit, fitting it with a heliport, which he smashed with a sledgehammer after the rejection. Despite the snub, when he learned of Kennedy's assassination he reportedly sobbed in his bedroom for three days. Sinatra worked with Hubert H. Humphrey in 1968, and remained a supporter of the Democratic Party until the early 1970s. Although still a registered Democrat, Sinatra endorsed Republican Ronald Reagan for a second term as Governor of California in 1970. He officially changed allegiance in July 1972 when he supported Richard Nixon for re-election in the 1972 presidential election.

In the 1980 presidential election, Sinatra supported Ronald Reagan and donated $4 million to Reagan's campaign. Sinatra arranged Reagan's Presidential gala, as he had done for Kennedy 20 years previously. In 1985, Reagan presented Sinatra with the Presidential Medal of Freedom, remarking, "His love of country, his generosity for those less fortunate... make him one of our most remarkable and distinguished Americans."

In June 1984, Sinatra performed at the a State Dinner in the White House honoring Sri Lankan President J. R. Jayawardena at the invitation of US President Ronald Reagan.

Santopietro notes that Sinatra was a "lifelong sympathizer with Jewish causes." He was awarded the Hollzer Memorial Award by the Los Angeles Jewish Community in 1949. He gave a series of concerts in Israel in 1962 and donated his entire $50,000 fee for appearing in a cameo role in Cast a Giant Shadow (1966) to the Youth Center in Jerusalem. On November 1, 1972, he raised $6.5 million in bond pledges for Israel, and was given the Medallion of Valor for his efforts. The Frank Sinatra Student Center at the Hebrew University of Jerusalem was dedicated in his name in 1978.

From his youth, Sinatra displayed sympathy for black Americans and worked both publicly and privately all his life to help the struggle for equal rights. He blamed racial prejudice on the parents of children. Sinatra played a major role in the desegregation of Nevada hotels and casinos in the 1950s and 1960s. On January 27, 1961, Sinatra played a benefit show at Carnegie Hall for Martin Luther King Jr. and led his fellow Rat Pack members and Reprise label mates in boycotting hotels and casinos that refused entry to black patrons and performers. According to his son, Frank Jr., King sat weeping in the audience at one of his father's concerts in 1963 as Sinatra sang " Ol' Man River," a song from the musical Show Boat that is sung by a black American stevedore. When he changed his political affiliations in 1970, Sinatra became less outspoken on racial issues. Though he did much towards civil rights causes, it did not stop the occasional racial jibe from him and the other Rat Pack members toward Davis at concerts.