A story my father likes to tell: It's the 60s, during his years in college in Chicago, and he's with his parents in Highland Park, Illinois for a High Holiday service at Congregation Solel (where I would become a bar mitzvah a few decades later). The rabbi announces from the bema that he will not be paying the portion of his taxes that pay for the Vietnam War. My grandfather bursts out laughing, and turns to his son to explain that the IRS would most likely end up taking more from the rabbi than they would if he'd paid his taxes on time and in full.
The rabbi was Arnold Wolf, who would later invite the Chicago Seven to speak at the temple (a costly decision -- the wealthiest member of the congregation, part of the prominent Pritzker family, responded by quitting and withdrawing his generous financial support). I bring this up because of reports of Obama asserting that he probably knows more about Judaism than any other president, and wondering why people question his support for Israel, and not John Boehner's or Mitch McConnell's, when he had so many Jewish friends in Chicago. Bill Kristol has an apt response to this, and John Podhoretz expounds upon how preposterous his boast about his knowledge is. But what neither of them focus on is who exactly Obama's Jewish friends in Chicago were.
As Adam Kredo detailed at the Washington Free Beacon in March, Obama was close to Rabbi Wolf (who lived in Hyde Park by the time Obama moved there) and his extremely left-wing milieu. The prevailing views on Israel in this circle were as far out as the prevailing views on everything else -- Wolf had advocated negotiating with the PLO long before its ostensible renunciation of terrorism -- and this influence on Obama's thinking has had real consequences:
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.
So yes, Obama had a lot of Jewish friends in Chicago. But his citation of the "some of my best friends are Jewish" trope as evidence of his pro-Israel cred is not only slightly offensive, it is, given who those friends actually were, completely nonsensical.
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