President Obama’s view of Israel was sharply influenced by Rabbi Arnold Wolf, a key member of a cadre of liberal rabbis and Jewish activists who blamed Israel for the failure to achieve peace in the Middle East and urged negotiations with the Palestine Liberation Organization while it carried out terrorist operations.
Wolf, who died in 2008, is remembered by those who knew him as a modern day Jewish "heretic" whose radical dogma on Israel and the American Jewish community traveled from a small Chicago synagogue all the way to 1600 Pennsylvania Avenue.
"Barack Obama knew many Jews in Chicago, but they tended to be left-wing Jews and tended to be people later involved in [the liberal advocacy group] J Street," explained Jonathan Sarna, a professor of American Jewish history at Brandeis University.
It is these liberal players who "bred in Obama a specific and subversive vision of American Jewish identity and of the Jewish state," Peter Beinart notes in his forthcoming book, The Crisis of Zionism.
Wolf in particular is said to have played a principal role in fostering Obama’s belief that the Jewish state—and, by proxy, the American Jewish establishment—could be pressured into negotiations with intransigent Palestinian political leaders.
"Barack Obama really believed there was this kind of a silent majority in the Jewish community who supports those views because those were the views he heard—liberal, active, Reform Jews in Chicago," added Sarna. "It was a shock to him when he found the majority of Jews are not that way."
One of principal architects of this radical Jewish philosophy was Wolf, who came to prominence in the late 1950s when he was hired as the full-time rabbi of Congregation Solel in Highland Park, a wealthy, liberal enclave on Chicago’s North shore.
During his stint at the temple, Wolf honed his left-wing bona fides, playing host to, among others, the infamous Chicago Seven, who were charged with inciting a riot at the 1968 Democratic National Convention.
In 1972, Wolf moved to Yale University where he served as a Jewish chaplain and director of the campus’s Hillel Foundation.
It was there that Sarna, then a student, first met Wolf.
"He enjoyed really being a little outrageous and riling people up," said Sarna, who became close with Wolf. "At a certain point he accused me of being a heretic. … He was full of mishegas," a Yiddish term for craziness.
"He was a colorful character and had no fear about taking controversial stances," added Rabbi Jack Riemer, a Florida-based religious leader who influenced President Bill Clinton. "Some people really considered him a heretic and saw what he was doing as outside the pale."
During the 1970s, Wolf established himself as one of the chief advocates of negotiations with the Palestine Liberation Organization, which, at the time, routinely orchestrated terrorist attacks against Israel.
As the head of Breira, a now-defunct Jewish group that met with the PLO in November 1976, before the militant group formally renounced terrorism, Wolf demanded that Israel cease being "intransigent" and learn to be "less arrogant," as its role "is not to rule but to serve."
"Arnold Wolf was one of the earliest Jewish public figures whose ‘love’ of Israel expressed itself in a relentless assault on the really existing Jewish state and a corresponding sympathy for its enemies," explained neoconservative author and commentator Norman Podhoretz.
"What Obama learned from [Wolf] about Israel would have been entirely consistent with what he learned from the likes of [the Rev.] Jeremiah Wright and [Palestinian activist] Rashid Khalidi, whose hatred of the Jewish state differed from Wolf’s views only in being more naked," Podhoretz said.
Obama initially became friendly with Wolf in the 1990s, when the rabbi served as the spiritual leader of KAM Isaiah Israel, a Chicago synagogue located across the street from the president’s former residence.
The future president was a regular guest at the synagogue and become close with a faction of Jews who shared Wolf’s views on Israel and the Middle East.
"It was clear to me talking to Arnie that he felt he knew this man [Obama] and had a role in shaping him," said Sarna. "Arnie did have a big influence."
Beinart, in a recent essay for Newsweek in which he argued that Obama has abandoned his liberal Jewish base, wrote: "Most of his key legal mentors were Jews (Abner Mikva, for example); many of his biggest donors were Jews; his chief political consultant, David Axelrod, was a Jew; he lived across the street from a synagogue. And for the most part, the Jews Obama knew best were progressives, shaped by the civil-rights movement and alienated from mainstream American Jewish organizations over Israel."
Wolf, in fact, is reported to have said that Obama’s stance on Israel is along "the line of Peace Now," a far left Israeli group that advocates in favor of international divestment from Jewish settlements.
Political insiders and Jewish thinkers believe that Obama’s early foray into the world of Jewish radicalism led him to take an aggressive and hostile stance against Israeli Prime Minister Benjamin Netanyahu early in his presidency.
"If you’re a non-Jew, as is the case of President Obama, and you’re in the progressive movement and meet progressive Jews who are ready to throw Israel under the bus, it can be hard for you to realize how pathological these people are, how out of the mainstream they are, how damaging they are even to non-Jews in their pursuit of moral perfectionism at any cost, including their own people," explained Richard Landes, a historian and professor at Boston University.
The Jewish left saw in Obama a new type of American leader, one who would buck the mainstream Jewish establishment and force Israel to accommodate the Palestinians at any cost, insiders say.
"The far left of the Israel-policy world saw an opportunity among all this promised hope and change to radically shift the agenda to their vision for the U.S.-Israel relationship," said one Jewish Democratic insider.
"He thought that to be effective, you have to be able to bring the Israelis and the intractable Palestinians to the table," explained the Democrat. "He believed that to bring the Palestinians to the table he needed to order an Israeli settlement freeze. And they did. But the Palestinians didn’t budge after getting what they demanded."
Obama’s roots in the activist world made him uniquely susceptible to ideas about Israel that fall far outside the mainstream American consensus, said a longtime Jewish insider who has ties to the White House.
"He comes from a perspective of being a left-wing radical agitator," explained the source. "Before he was a senator and a state legislator, he was from a milieu of the left, in and around campuses and community organizing, that sees Israel and Zionism as being an imperial force that unfairly oppresses the Palestinian masses."
Mid-presidency, after numerous flare-ups with the American Jewish community and Israeli government, team Obama launched a charm offensive meant to set his relationship with the pro-Israel community back on track.
"He began to realize—or his advisers told him—that KAM and the people he knew are not a microcosm of the Jewish community," Sarna explained.
High level officials like Rahm Emanuel, then Obama’s chief of staff, told Jewish leaders that Obama had "screwed up the messaging" on Israel. The president’s Middle East point man, Dennis Ross, touted supposed "manifestations of the change" in how the administration would treat Israel.
"There’s widespread understanding, including in the administration, that the … approach of placing Israeli settlements as the central barrier to solving every issue in the Middle East was wrong," noted the Jewish Democratic insider.
The administration’s recalibration, however, was relatively short lived.
"He reignited the concerns of the Jewish community" with that speech, said the senior Jewish insider, who went on to note that the Jewish community has concerns about a potential second term.
"There are grave concerns that during his second term, when he no longer has to worry about mundane matters of electoral politics, that the real Barack Obama will come forward," said the source. "Bibi Netanyahu better watch out."