Yes He Did: My White Girlfriend Inspired Obama’s Big, Dark Regina in Dreams from My Father

John C. Drew Ph.D. by John C. Drew Ph.D. on July 18th, 2012

This is article 1 of 44 in the topic Obama, Who Is He?
John Drew and Caroline Boss

in June 1980.

As far as I know, I am the only person in the nation willing to verify that young Barack Obama was an ardent Marxist-Leninist. 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 and that I was in no position to verify his most private ideological views. I am expecting that these defenses of young Obama’s credentials as a pragmatic centrist will fall apart now that David Maraniss has revealed in Barack Obama: The Story that the Occidental College coed 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 Pulizer Prize winning journalist, Obama created the composite character Regina out of the European adventures of a 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. This somewhat disconcerting news came to my attention last month along with the even more shocking news that the very name Regina was the name of Boss’s real life grandmother, a Swiss woman who worked as a maid.

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 new book, The Communist: Frank Marshall Davis: The Untold Story of Barack Obama’s Mentor. There, Kengor reports on my relationship with Boss along with details of a heated debate over the 1980 Christmas break where I confronted the impracticality of 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 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 Kurdow 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 pony tail. 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 – who 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 overalls. I clearly remember 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 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 Stalinist leader as I remember her as an uninhibited girl with a permanent, mischievous smile who pushed the boundaries of social norms.

Boss appeared in her own Occidental College magazine, Tattooed Lady, as a tasteful nude in a manner that still reminds me of Gwyneth Paltrow in the film Great Expectations. At Occidental, my circle of radical friends deeply enjoyed mixing politics with art, literature, film and photography. According to Maraniss, Boss is the person who referred young Obama to her friend, Lisa Jack, the student photographer for whom young Obama posed in those now famous photographs that document his straw hat and rakish style as a cigarette smoking freshman.

I remember that my Marxist girlfriend was bookish, but struggled in school. As I recall, she often failed to turn in papers on time and piled up strings of incompletes that would stretch out her academic career. As I recall, she would take about five years to finish the normal four year program 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.

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 from My Father. In 2011, for example, I was interviewed by David Garrow – a Pulizer Prize winning author himself – and I quickly discovered that Garrow was less interested in my college or graduate school memories than he was in 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. There were numerous clues that matched up with my memories of Boss including the fact 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 it was open at the times when you could not get a meal at the student union and because we could smoke our Marlboro Light cigarettes.

Similar to the character Regina, Boss expressed an exceptional interest in my graduate school papers, what I was reading, and my future ambitions as a scholar. Her positive vision for my future as a great scholar was a striking contrast to my own family’s lack of support. In retrospect, Boss’s interest in my academic work was particularly noteworthy since even subsequent girlfriends displayed only the most cautious indifference to my political science research. (In spite of them, my doctoral dissertation ended up winning the William Anderson Award from the American Political Science Association.)

Boss, as I recall, fed into my ambitions. In one of the many cards and letters she sent me, she wrote: “Go for greatness!”

Much like 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 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 supportive Caroline Boss I knew between 1979 and 1981.

Obama’s Regina, however, struck me as distant from Boss’s life when Regina begins to share that she grew up in Chicago, with an absent father and struggling mother. This is because the real life Regina I knew had been adopted by her Swiss parents. Boss, in fact, had grown up as the only child of a wealthy family. (A younger brother had died in early childhood.) In contrast to Regina’s poverty, the real life Boss family lived in a spacious house with a pool in the Portola Valley – close to both San Francisco and Stanford University in Palo Alto.

Boss’s father was very much alive. Mr. Boss was a gruff, materialistic Swiss businessman who was more than happy to share with me the fact that he could live a much richer lifestyle in California than he could in his native Switzerland on the same annual income. I remember him once disparaging a waitress who was doing an exceptional job of serving us at a Lawry’s Restaurant. “She thinks she has a good job,” Mr. Boss remarked.

Looking back, I think I had more rapport with Boss’s adopted mother. She had refined tastes in antiques and jewelry. I remember Mrs. Boss wore a huge diamond ring. She once shared a story about how she had evaded a mugging attempt inspired, in part, by the size of that diamond. Mrs. Boss also enjoyed giving lavish gifts to her daughter and taking her on shopping sprees at the most elite stores in San Francisco. Around graduation time, Mrs. Boss even talked her daughter into cutting off her woven ankle bracelet so that she would wear a pretty formal dress with nylons.

In understanding Boss’s role in Dreams from My Father, however, I think it is important to point out she was not a spoiled rich kid.

Although she had her own car and could afford her own apartment, she did work as a house cleaner on the side to make money. For example, I remember vividly 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 rude treatment Obama and his friends offered their maids when they messed up their Haines Hall dorm rooms and hallway.

I would not be surprised to learn Boss might have lectured young Obama on the value of housework and on the importance of not making fun of people, like her grandmother, who worked as maids.

Politically, the most significant issue missing from Obama’s composite Regina is that the real life Caroline Boss was 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 held a leadership role on campus because she was one of the main speakers at the anti-apartheid event on February 18, 1981. In Maraniss’s book, the young Obama’s stirring portrayal of a soon to be arrested South African activist offers a stark contrast to Boss’s speech in which – reminiscent of Phoebe Buffay – she is so nervous that she flubs the introduction of the guest speaker, a visitor from South Africa named Tim Hgubeni.

Looking back on my own memories, 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 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 the story of my real life white girlfriend would not have scored Obama many points among his potential black constituents in Chicago. Acknowledging the influence of the white, Swiss-American Boss would have called attention to the fact that virtually all of the women who played an intense role in young Obama’s life were white and not black.

Moreover, if Obama had been deeply in love with Boss, then the story might have revealed his discomfort with the way I would routinely disrupt his romantic plans through my frequent visits to the Occidental campus. (Maraniss, oddly enough, does discuss how Boss’s future husband, Thomas Grauman, battled with young Obama for the attention of Alexandra McNear.) More significantly, if Obama told a story about the influence of the real life, white Regina, it would show Obama had little interest in black girls and instead displayed much greater interest in hanging out with – and perhaps falling in love with – wealthy white girls including Caroline Boss, Alexandra McNear and Genevieve Cook.

Finally, a white Regina would have more quickly led objective readers to the real Barack Obama, the young guy I met during Christmas break in 1980 who seemed like a white guy to me. It might have more quickly introduced the American people to the prickly young Obama, the one who got in my face when I confronted his naïve faith in a Communist revolution.

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