The Vetting: Like My ‘Compressed’ Ex-Girlfriend, Obama Was ‘An Ardent Marxist Socialist’ in College

The collegiate Obama was an ardent Marxist socialist extremist. I confronted young Obama’s naïve faith in an inevitable Communist revolution when he visited the San Francisco area during his Christmas break from Occidental College in 1980–at the Boss family’s home in Portola Valley, CA, a small city outside of suburban Palo Alto, south of San Francisco.

[Regina] told me about her childhood in Chicago, the absent father and struggling mother, the South Side’s six-flat that never seemed warm enough in winter and got so hot in the summer that people went out by the lake to sleep….Her voice evoked a vision of black life in all its possibility, a vision that filled me with longing–a longing for place, and a fixed and definite history. As we were getting up to leave, I told Regina I envied her. “For what?” “I don’t know. For your memories, I guess.”

That passage, from Obama’s (first) autobiography, Dreams from My Father: A Story of Race and Inheritance (pp. 158-9), describes “Regina,” a young black woman at Occidental College whom he claimed was crucial to his political awakening. She even encouraged him to drop “Barry” in favor of “Barack.” He envied her confidence, and her memories–so much so, in fact, that he made them up. Not only was “Regina” not from the poor South Side of Chicago; she was not even black.

I know, because she was my girlfriend at the time.

The real “Regina” was Caroline Boss (now Caroline Grauman-Boss). That revelation is one of many in David Maraniss’s new biography, Barack Obama: The Story. Maraniss shows that Obama created “composite” or “compressed” characters, including girlfriends, in his memoir to conceal their identities, or as a literary device. Maraniss confirms that Obama’s “Regina” was, in fact, Boss, whom I dated from 1979 to 1981, when Obama was at Occidental. Maraniss confirms that she was close to Obama. But Maraniss also covers up Obama’s Marxist radicalism by casting Obama as more centrist than Boss or than his roommate, Hasan Chandoo (Maraniss 368).

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