My White Girlfriend Inspired Obama's Big, Dark Regina in Dreams from My Father

As far as I know, I am the only person in the world willing to verify that young Barack Obama was an ardent Marxist-Leninist. My face-to-face report on how I confronted young Obama's ideological extremism is now featured in Paul Kengor's new book, The Communist - Frank Marshall Davis: The Untold Story of Barack Obama's Mentor.

Bloggers who have sought to discredit my story have asserted that I never met young Obama, that I was not part of young Obama's inner circle of friends, and that I was in no position to verify his most private ideological views. I am expecting these fragile defenses of young Obama's credentials as a pragmatic centrist will fall apart now that David Maraniss's Barack Obama: The Story reveals that the Occidental College girlfriend who introduced me to young Obama was one of the inspirations for the composite character "Regina" in Obama's Dreams from My Father. True, Regina appears in Dreams as "a big, dark woman," but why deny Obama a little poetic license?

According to Maraniss, a Washington Post editor and Pulitzer Prize-winning journalist, Obama created Regina out of the European adventures of a young black female student at Occidental named Sarah Etta-Harris, the Chicago family stories of Michelle Robinson -- the president's future wife -- and anti-apartheid activism of my then-22-year-old white girlfriend, Caroline Boss (now Caroline Grauman-Boss). This somewhat disconcerting news came to my attention last month along with the even more telling news that the name "Regina" was the name of Boss's real-life grandmother, a Swiss woman who worked as a maid. In Dreams, you may recall, Regina is such a central figure in young Obama's life that, along with Obama's Communist mentor, Frank Marshall Davis, she is remembered as one of the key reasons why young Obama chose to become a community organizer.

When I first read Dreams in 2008, I remember thinking the character of Regina reminded me of Boss, a girl I dated and lived with -- off and on -- for slightly over two years between the spring of 1979 and the spring of 1981. Much of the information I have shared about my relationship with Boss has recently been published in Paul Kengor's The Communist. There, Kengor reports on my romance with Boss, along with details of a heated debate over the 1980 Christmas break, where I confronted the impracticality of her and Obama's anticipation of an inevitable Communist revolution.

Obama introduces composite Regina by writing: "I had seen her around before, usually sitting in the library with book in hand, a big, dark woman who wore stockings and dresses that looked homemade, along with tinted, oversized glasses and a scarf always covering her head" (Dreams, pp. 103-104). In contrast to this description, I can report that the real Regina was a fun, scintillating, hyper-extraverted figure on the Occidental College campus. In contrast to the seriousness of Michelle Obama, I would say the young Caroline Boss was more like that character played by Lisa Kudrow on Friends -- the fiercely independent, quirky, nurturing Phoebe Buffay.

Like Phoebe, Boss had long blond hair, which she wore pinned back in a bun or twisted up in a ponytail. Her posture was terrible. When she stood up at her full 5'8" height, however, she was somewhat taller than me -- especially in her clogs. By the time Boss introduced me to young Obama -- whom she had known for almost one year -- she was a thin, almost anorexic girl. I remember she dressed like a hippie from the 1960s, complete with a woven ankle bracelet, blouses that reflected her Swiss heritage, and big colorful Indian print skirts. Boss did wear big sunglasses. She was also fond of wearing scarves round her neck. I cannot remember her ever wearing a scarf over her head. What I recall best about her clothing was that she had a habit of wearing shirts tucked inside bulky light blue overalls. I clearly remember that the real Regina also had a sensible, if somewhat guilty, appreciation for the superior fit of designer jeans from Gloria Vanderbilt.

In contrast to the composite Regina, Boss was a Marxist and a socialist looking forward to a Communist revolution in the United States. She believed that this revolution would be the inevitable result of larger social forces working through the dialectic logic of Marx's scientific socialism. In the end, however, I do not remember Boss so much as a campus Stalinist leader as I remember her as an uninhibited girl with a permanent, mischievous smile who pushed the boundaries of social norms. I remember that Boss appeared in her own Occidental magazine, Tattooed Lady, as a tasteful nude in a manner that still reminds me of Gwyneth Paltrow in the film Great Expectations. Consistent with my circle of radical friends at Occidental, Boss enjoyed mixing Marxist feminist politics with art, literature, film, and photography. Accordingly, I am not surprised that Maraniss indicates that Boss was the model scout who introduced young Obama to Lisa Jack, the student photographer who captured him posing, Choom Gang-style, with a cigarette on his lips and a straw hat on his head.

I remember that my Marxist girlfriend was bookish, but she struggled in school. As I recall, she often failed to turn in papers on time and piled up a string of incompletes that would stretch out her academic career. She would take about five years to finish the normal four-year course at Occidental. She ended up being something of a perpetual student. Although I lost track of her whereabouts in 1982, I learned later that she earned an M.S. in political philosophy from the London School of Economics and another M.Phil. in politics from Columbia University. Given her educational experiences, it is not hard for me to imagine that Boss's intense interest in politics might have made for good reading in a more truthful version of Dreams. When I was interviewed by historian David Garrow in December 2011, for example, I quickly discovered that this Pulitzer Prize-winning author was nonchalant about my memories, but positively gleeful about a tattered green address book that contained Boss's old contact numbers.

Although I was thrown off by Obama's statement that Regina was "a big, dark woman," I had noticed highly significant traces of Boss in the character Regina. For example, she and I had both enjoyed -- practically lived in -- Occidental's on-campus coffee shop, The Cooler. As I recall, The Cooler was the center of our lives because you could eat there when you could not get a meal in the student union, and because we could smoke our Marlboro Light cigarettes as we read our books and sipped our coffee.

Similar to the character Regina, Boss expressed an exceptional interest in my graduate school papers, my reading assignments, and my future ambitions. Her confidence in my future as a great scholar and as a revolutionary political leader was a striking contrast to my own family's lack of support. In retrospect, Boss's interest in my academic studies was particularly noteworthy since subsequent girlfriends displayed only the most cautious, bemused indifference to my research. (In spite of them, I ended up teaching at Williams College and winning the William Anderson Award from the American Political Science Association by the late 1980s.) Boss, as I recall, was the only person in my life to applaud my sense of mystic destiny. In one of the many cards and letters, she wrote: "Go for greatness!"

Similar to the Boss I remember, the character Regina is highly curious about Obama's reading and academic work. Regina speaks in such an overwhelmingly encouraging and uplifting fashion that she seemingly transforms the young Obama. Referring to his heart-to-heart with Regina, Obama later writes: "Strange how a single conversation can change you" (Dreams, p. 105). I can report that those vignettes featuring Regina are an accurate echo of the curious, enthusiastic, and intellectually vibrant Caroline Boss I knew between 1979 and 1981.

Obama's Regina, however, struck me as distant from Boss's real life story when Regina begins to share that she grew up in Chicago, with an absent father and struggling mother. This is because Boss had been adopted and had grown up as the only child of a wealthy Swiss-American family. (Tragically, a younger brother had died in early childhood.) In contrast to Regina's poverty, the real-life Boss family lived in a spacious home with a pool in the Portola Valley, close to both San Francisco and Stanford University in Palo Alto. Boss's father was very much present in her life. He was a gruff, materialistic businessman who was more than happy to share with me that he could live a much richer lifestyle in California than he ever could in his native Switzerland. I remember him once disparaging a waitress who was doing an exceptional job of serving us prime rib at a Lawry's Restaurant. "She thinks she has a good job," Mr. Boss remarked.

Looking back, I suspect I had more rapport with Boss's adopted mother. She had refined tastes in antiques and jewelry. I remember that Mrs. Boss wore a huge diamond ring. She once shared a story about how she had evaded a clumsy robbery attempt inspired, in part, by the size of that diamond. Mrs. Boss also enjoyed giving expensive gifts to her daughter and taking her on shopping sprees at the most elite stores in San Francisco. Around graduation time, I remember that Mrs. Boss surprised me when she talked her somewhat stubborn daughter into cutting off that silly woven ankle bracelet -- the significance of which was beyond my understanding -- so that her daughter could attend a party in a formal dress with nylons.

In understanding Boss's role in Dreams from My Father, however, I think it is important to point out that she was not at all a spoiled rich kid. Although she had her own car and could afford her own apartment, she did part-time work as a house cleaner. For example, I remember that Boss had a job cleaning the home of one of Occidental College's political science professors, Jane Jacquette. In Dreams from My Father, Barack Obama makes a big deal about Regina being angered at the thoughtless mess Obama and his friends left behind for the maids to clean in their Haines Hall dormitory. I would not be surprised to learn that Boss might have lectured Obama on the humanity of their maids and on the importance of not making fun of people like her, or her grandmother, who worked at home-cleaning jobs.

Politically, the most significant issue missing from Obama's composite Regina is that the real-life Caroline Boss was then a strongly committed Marxist socialist. Boss served as the co-president of the Democrat Socialist Alliance (DSA) at Occidental College while Obama was a sophomore. We also know, from David Maraniss's book, that Boss she was one of the main speakers at the anti-apartheid event at Occidental on February 18, 1981. In Maraniss's book, Obama's smooth participation in skit where he plays the role of a soon-to-be-arrested South African activist offers a stark contrast to Boss's performance in which -- reminiscent of Phoebe Buffay -- she nervously flubs the introduction of the guest speaker, a visitor from South Africa.

All in all, I think it is safe to say the story of the real-life Caroline Boss would have been much more interesting than the story of the fake Regina -- even the parts of the fake Regina that seem to drawn on the real life of the first lady, Michelle Obama.

I am asking myself, why would Obama delete a vivid white girl from his autobiography and replace her with a big, dark composite character from Chicago?

As a political scientist, I think the best theory is that my girlfriend's story would not have scored Obama many points among his potential black constituents in Chicago. Acknowledging the influence of a white Swiss-American would have called attention to Obama's politically incorrect attachments to a series of wealthy white females including Caroline Boss, Alexandra McNear, and Genevieve Cook. It would have reminded readers that Obama picked Occidental College, in part, because of the advice of a white girl from the wealthy Brentwood area of Los Angeles. Ultimately, I think the story of the real white Regina would have led readers to the uncomfortable realities of the real young Obama -- the Punahou graduate who seemed completely white, the cocaine user who benefited from affirmative action, and the angry dude who got in my face to defend his naïve faith in an inevitable Communist revolution.


John Drew

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