‘Mr. Sinatra Adored Israel, and Israel Adored Him Back.’

2015 is the year of the Frank Sinatra Centennial, and though the great singer’s 100th birthday won’t be marked until December, it seems only proper to remember the Chairman of the Board’s deep and abiding commitment to Israel, which he saw as an integral part of the chain of liberal causes that he supported throughout his career. His activities on behalf of the Jewish state started with smuggling money to the Haganah under the British Mandate. Starting in the 1950s, his records and films were banned in Arab counties because of his sympathies with Zionism. He performed for IDF troops, and in the 1970s and ’80s he raised millions of dollars for student centers in Nazareth and Jerusalem.

Sinatra’s initial visit to Israel came in 1962, as part of his first world tour. At the height of his popularity, his managers wanted him to embark on a series of concerts that would take him as far as Japan. Sinatra also had personal reasons for touring: His falling out with the recently elected JFK and the rest of the Kennedy clan, due to a combination of Sinatra’s volatile temper and allegations concerning the singer’s links to organized crime, hurt him deeply. Sinatra turned toward reviving his own career and stepped up his charitable work, which his managers hoped would “temper the image of the flip playboy.”

In May and June of 1962 Sinatra gave 30 concerts in cities around the world. A percentage of the proceeds went to children’s charities. The tour began in Tokyo, where legions of fans turned out see and hear the singer. Because Israel appeared on Sinatra’s schedule, the Arab League rejected proposals that he perform in Cairo and Beirut.

Israel—and the response to European persecution that it embodied—was a deeply personal cause for Sinatra. He was born and brought up in an Italian-American enclave in Hoboken, New Jersey; his grandparents had emigrated to the United States from Italy in the 1890s, and the anti-immigrant bigotry they faced in turn-of-the-century New York still lingered in Frank’s childhood in the 1920s. He told his friend Pete Hamill that “growing up, I would hear the stories … things that happened because you were Italian … the stories were there. The warnings, the prejudice you heard about it at home, in the barbershop, on the corner. You never heard about in school. But it was there.”

These experiences of prejudice made the young Sinatra aware of other forms of bigotry, including anti-Semitism. And there were Jewish connections in his Hoboken childhood. Among his caretakers (Frank’s mother worked often outside of the home) was a Mrs. Golden. She spoke to him only in Yiddish, and in his adulthood Sinatra often joked that he “knew more Yiddish than Italian.” For decades Sinatra wore a Jewish star pendant that Mrs. Golden had given him.

The most famous musical expression of Sinatra’s brand of urban ethnic liberalism was the short film The House I Live In, produced in 1945. The enduring line of its title song was “The children in the playground, the faces that I see all races and religions, that’s America to me.” The film opens with a shot of Sinatra leaving a band rehearsal and encountering a charged encounter between a gang of school children and a Jewish-looking boy. Telling the kids not to be “suckers,” the singer separates them from the boy and tells them that racial and religious distinctions “make no difference except to a Nazi or somebody as stupid.” To Hollywood gossip columnist Louella Parsons Sinatra said, “Children themselves are not to blame for religious and racial intolerance. It’s the parents … kids hear their parents talking about the McGinty’s or the Ginsbergs and think there must be something awfully wrong with being a Catholic or a Jew.”

The short film won a special Academy Award and was shown across the United States. It could not have escaped Sinatra’s attention that the creators of the film—the director, the screenwriter, and the songwriter—were Jews on the political Left.

Civil rights was another keystone of Sinatra’s early liberal agenda. Beginning in the mid-1940s Sinatra used his considerable influence to advocate for equality for African Americans, particularly for those in the entertainment industry. As historian Jon Weiner noted in his essay “When Old Blue Eyes was Red,” “What other star at the top of the charts had thrown himself in the civil rights struggle so directly?”

In 1947, two years after filming The House I Live In, Sinatra appeared at a benefit concert for the Zionist cause at the Hollywood Bowl. The event was titled “Action for Palestine.” A crowd of 20,000 wildly applauded their idol and called for approval of the partition plan then being deliberated at the United Nations.

The following year, at the request of Zionist leaders, Sinatra smuggled a large amount of money to operatives buying arms for the Haganah. He had been asked smuggle the money by Teddy Kollek, then the Haganah representative in the United States. Kollek had purchased a large arms shipment in New York and had to pay the ship’s captain to take it to Palestine. He knew that he was being followed by Federal agents. To evade them, Kollek asked Sinatra, who was performing at the Copacabana nightclub, to help him evade their surveillance. In Kollek’s words, “In the early hours of the following morning I walked out the front door of the building with a satchel, and the Feds followed me. Out the back door went Frank Sinatra, carrying a paper bag filled with cash. He went down to the pier, handed it over, and watched the ship sail.” Years later Sinatra told his daughter Nancy that he did this for the Israelis because, “I wanted to help, I was afraid they might fall down.”

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So, when Sinatra came first to Israel in 1962, his view of the country was conditioned by his liberal, and one might say philo-Semitic, world-view, and by a specific loyalty to Zionism. In the American centrist-liberal consensus of the early 1960s, Israel was a just cause: Jews were a minority group that had been persecuted and murdered in Europe, and they needed a safe haven in their historic homeland of Palestine, which they had been promised for decades under international law.

During his 1962 international tour Israel was the country where Sinatra had scheduled the most concerts: seven in six cities. The money from those concerts was earmarked for the building of the “Frank Sinatra International Youth Center” in Nazareth. It was envisioned as a center for both Jewish and Arab youngsters. It seems that Sinatra imagined that his American liberal vision of a “melting pot” in which all prejudice would be dissolved—the message of The House I Live In—could be transferred to Israel, where he made the case for a center that would provide equal opportunities for Jewish and Arab youngsters.

Sinatra’s Israel concerts coincided with the nation’s 1962 Independence Day Celebrations. (It was Israel’s 14th Independence Day.) He was invited to the official events and sat with Prime Minister David Ben Gurion and Gen. Moshe Dayan at the Independence Day reviewing stand. At the paratrooper training base at Tel Nof Sinatra gave a concert for the troops. Some of that concert was captured on film and included in the 1962 documentary film Sinatra in Israel.

But the richest record of Sinatra’s first Israeli visit comes to us from the pen of Sinatra’s African-American assistant George Jacobs. In his tell-all book Mr. S.: My Life With Frank Sinatra, Jacobs gave a vivid report on their Israeli sojourn and its significance for both himself and his boss. Jacobs writes:

After our week in Hong Kong we flew on to Israel. Mr. S adored Israel, and Israel adored him right back. Here was a whole country of underdogs and survivors, the people Sinatra respected most, people like himself who had beaten the odds. … Israel was the only place on the whole tour where Mr. S took a real interest in the country as anything other than a concert stop. He wanted to see everything, and Israel rolled out the red carpet. When he wanted to cross the Sea of Galilee and see the Golan Heights, the Israelis contacted the Syrians to tell them that our long convoy was not a troop movement and to hold fire. The sundown on the Sea of Galilee was beautiful. “Another few days and I could become a believer,” Mr. S half-joked.

Sinatra and George Jacobs joined Ben Gurion and Dayan on the reviewing stand and were able to pass through Jerusalem’s Mandelbaum Gate border-crossing with Jordan and visit the Christian Holy Sites. Sinatra, brought up in the Catholic Church, was eager to visit the sites associated with the life of Jesus. And it was this same impulse that drew him to visit Nazareth a number of times and led him to fund the building of a Catholic church there that would bear his name.

After their visit to the Jordanian side of the border Sinatra and Jacobs returned to Israeli West Jerusalem for a visit to Yad Vashem. Of this visit George Jacobs wrote:

Most moving for both Mr. S and me and was The Yad Vashem Holocaust Memorial on the Hill of Memory, where all the trees had been planted in memory of the victims. This was stunning and solemn place. The external beauty of the land of milk and honey contrasted with the horrors shown within, particularly the underground Children’s Museum, where each of the more than one million tiny lights represented the life of a child that had been snuffed out. Afterward Mr. S said the visit had made him feel rotten about not fighting in World War II and that Israel was “a wonderful country worth dying for.”

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In 1964 , two years after this initial visit, Sinatra, again accompanied by Jacobs, returned to Israel to dedicate the Nazareth Youth Center’s building, and once again he was honored by the Israeli public and by the nation’s officialdom. A year later, Sinatra returned for the filming of Cast a Giant Shadow, Kirk Douglas’ Hollywood epic about the founding of Israel. The film was about the Israeli military and the role than an American officer, Col. Mickey Marcus, played in its formation.

When offered a cameo role as an American fighter pilot who agrees to help the new Israeli Air Force, Sinatra readily agreed. In 1965 Sinatra’s affection for Israel and Israelis was as strong as it had been in 1948. Kirk Douglas offered Sinatra what was at the time a huge sum—$50,000—to appear briefly in the film. Sinatra donated his fee for the role directly to his Nazareth Youth Center.

Sinatra’s role, as a devil-may-care war hero pilot, is not quite convincing. An irony not lost on many in the film’s audiences was that Sinatra himself had never served in the American army during the war. (He had a medical exemption.) As critic Francis Davis noted: “Sinatra spent the Second World War in uniform only on screen, where he always seemed to be on leave or having just been discharged.” Despite all of the good intentions (and Sinatra’s cameo) Shadow was a flop.

In this film , as in Exodus, released a few years earlier, the Israelis are the good guys, or “cowboys,” and the Arabs are the “Indians.” The good-triumphs-over-evil theme is so blatant in this film that the viewer is left with the impression that there couldn’t possibly be another side to the story. As New Yorker critic Brendan Gill remarked, it is “an embarrassing movie … another exercise in movie biography that may be filed as a case of mistaken identity: any resemblance to persons living or dead is sacrificed to make elbow room for hero Kirk Douglas.”

As Sinatra became a Nixon supporter in the 1970s and a Reagan supporter in the 1980s, he could still stay connected to the Israeli cause, even though Israel no longer appeared to many to be the underdog. For by the early 1980s U.S. support of Israel became a conservative cause; and many liberals were becoming disenchanted with Israeli policies in the Occupied Territories. In the mid-1970s Sinatra raised $1 million to build a student center on the Mt. Scopus Campus of Hebrew University in Jerusalem; the center was named in his honor in 1978. This center, like the one Sinatra had established in Nazareth in 1964, was to be for both Jewish and Arabs students. Yet as with the center in Nazareth, it doesn’t seem that Sinatra, the other donors, or their Israeli interlocutors addressed in any serious fashion how this American-style liberal agenda might be effected within an Israeli context. Tragically, this student center became famous decades later because of a Palestinian terrorist bombing there in 2002, in which nine people, among them a number of American students, were killed.

On Sinatra’s lifelong connection to Israel I think that his assistant George Jacobs should get the last word:

We often returned to Israel, which Mr. S decided was his favorite country. Mr. S often boasted he was “King of the Jews.” He donated big money to Zionist causes, and would plug the place every time he had a chance.

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Shalom Goldman is scheduled to speak on Frank Sinatra at 100: The Israeli Connection, Tuesday, June 9 at Tmol Shilshom, Jerusalem’s famed literary café, with music by Emmy Raviv.

Shalom Goldman is Professor of Religion at Middlebury College. His most recent book is Starstruck in the Promised Land: How the Arts Shaped American Passions about Israel.