Barack Obama’s Missing Girlfriends

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©Jack Cashill - April 18, 2010

The blogosphere abhors a vacuum. So when the mainstream media (MSM) leave holes in a given narrative—in this case, the biography of the president—bloggers individually, incrementally, and indefatigably strive to fill in the blanks, sometimes successfully, sometimes less so.

In his comprehensive, 600-plus page biography of Barack Obama, The Bridge, New Yorker editor David Remnick lays down the baseline of what the mainstream media know about the president—or at least what they want us to know.

Where Remnick falls oddly silent—not even to scold the blogosphere, which he does often--is on the question of Obama’s love life. This would not be particularly noteworthy save that Obama’s 1995 memoir, Dreams From My Father, is in large part a racial coming-of-age story.

In Obama’s all-consuming search for identity, and in Remnick’s effort to document that search, Obama’s romantic life should surely have been part of the narrative. Whether he dated white women or black women—and what he might have learned from either--matters.

In Obama’s ten years of bachelorhood before he met Michelle in 1989, Remnick creates a credible picture of him as a popular, good-looking, man about town. Obama’s Chicago mentor Jerry Kellerman tells Remnick that Obama dated various women and “was more than capable of taking care of himself.” Another Chicago friend, John Owens, claims, “Barack tends to make a strong impression on women.” And Remnick refers specifically to an “old girlfriend” that Obama rather coolly abandoned upon leaving Chicago for Harvard in 1988.

And yet, unless I missed something, despite scores of interviews with Obama acquaintances, never do we actually hear from a woman who dated Barack Obama. The same vacuum is apparent in the book, Barack and Michelle, Portrait of an American Marriage, by Christopher Andersen. Andersen quotes Obama’s New York roommate, Sohale Siddiqi on the subject of Obama’s allure--“I couldn’t outcompete him in picking up girls, that’s for sure”—but we do not hear from any of the girls he might have picked up or dated.

In Dreams, Obama creates a similarly romantic image of himself. At one point, when his half-sister Auma visits him in Chicago pre-Michelle, he tells her about a ruptured relationship with a white woman back in New York. He adds, with more than a little calculation, “There are several black ladies out there who’ve broken my heart just as good,” but we do not read as much as a single sentence about any of these black women.

In Dreams, Obama recalls his early days in Indonesia when he began to notice “that Cosby never got the girl on I Spy.” Curiously, in his own book, he does not do much better.

In Dreams, in fact, the only lover Obama talks about is the mystery woman in New York. Although he speaks of her only briefly and in retrospect, he does so vividly and lovingly. “She was white,” he tells Auma. “She had dark hair, and specks of green in her eyes. Her voice sounded like a wind chime.” This is no casual relationship. “We saw each other for almost a year. On the weekends, mostly. Sometimes in her apartment, sometimes in mine.”

One weekend the woman invites Obama to her family’s country home, which had been her grandfather’s, and “he had inherited it from his grandfather.” The library is filled with old books and photos of the grandfather with presidents, diplomats, industrialists. “It was autumn,” Obama recalls, “beautiful, with woods all around us, and we paddled a canoe across this round, icy lake full of small gold leaves that collected along the shore.”

It is during this memorable weekend that Obama experiences something of a racial epiphany. “I realized that our two worlds, my friend’s and mine, were as distant from each other as Kenya is from Germany. And I knew that if we stayed together I’d eventually live in hers.“ This realization inspires him to break off this relationship despite a gracious reception by her parents.

Remnick concedes that Dreams is not to be taken at face value. He calls it a “mixture of verifiable fact, recollection, recreation, invention, and artful shaping.” On any number of points, all fairly trivial, he attempts to sort out the fact from the fancy. On the subject of this critical relationship, the one and only in Dreams before Michelle, he falls conspicuously silent. The reader of The Bridge would not know Obama had such a relationship.

Christopher Andersen was more curious but made little headway in confirming the story or identifying the woman. “No one,” he writes, “including his roommate and closest friend at the time, Siddiqi, knew of this mysterious lover’s existence.”

Abhorring a vacuum, I have ventured to fill it. Given Remnick’s list of the allowable ways to interpret Dreams-- verifiable fact, recollection, recreation, invention, and artful shaping--I choose “D” for the mystery woman, “invention.” In the absence of any contrary information, best evidence argues for an invention largely of Ayers’ contrivance.

As I have argued from textual analysis, and Andersen has confirmed from his own reporting, Obama had help with the book. As Andersen tells it, after four futile years of trying to finish the contracted book, a "hopelessly blocked" Obama delivered his family's "oral histories, along with his partial manuscript and a trunkload of notes" to “friend and neighbor” Ayers for a major overhaul.

Ayers appears to have taken Obama’s shapeless mass of a manuscript and fitted it into an Homeric framework. We know that Ayers is keen on the classics. Early in his own 2001 memoir, Fugitive Days, he tips his Homeric hand. "Memory sails out upon a murky sea-wine-dark, opaque, unfathomable," he writes with a knowing wink. "Wine-dark sea" is trademark Homer.  Ayers seems to have had fun with the project.

Indeed, in January 2009, Michiko Kakutani, the New York Times literary critic, described the structure of Dreams as "a quest in which [Obama] cast himself as both a Telemachus in search of his father and an Odysseus in search of a home.” Three weeks earlier, I had made the identical argument on these pages.

Any number of incidents in Dreams recall Homer’s Odyssey. In his quest, Obama encounters blind seers, lotus-eaters, the "ghosts" of the underworld, whirlpools, a half dozen sundry "demons," and even a menacing one-eyed bald man. These encounters likely run the full range of stylistic possibilities from verifiable fact to artful shaping to pure invention.

The mystery woman recalls the temptress Circe. Like Obama's unnamed girlfriend, Circe lives in a "splendid house" on "spacious grounds." She too wants her lover, Odysseus, to stay forever. Like Obama, Odysseus has shared his bed with this alien seductress for one year. But her world can never be his.

"You god-driven man,” Odysseus's mates warn him, “now the time has come to think about your native land once more, if you are fated to be saved and reach your high-roofed home and your own country." (Ian Johnston translation)

If Obama's friend nicely fills the Circe role, she is almost surely grounded in the real life person of Diana Oughton, Ayers's lover who was killed in a 1970 Greenwich Village bomb factory blast. Ayers was obsessed with Oughton. In Fugitive Days, he fixes on her in ways that had to discomfort the woman that he eventually married, their fellow traveler in the Weather Underground, Bernardine Dohrn.

Physically, the woman of Obama’s memory with her “dark hair, and specks of green in her eyes” evokes images of Oughton. As her FBI files attest, Oughton had brown hair and green eyes. The two women shared similar family backgrounds as well. In fact, they seemed to have grown up on the very same estate.

According to a Time Magazine article written soon after her death, Oughton “brought Bill Ayers and other radicals” to the family homestead in Dwight, Illinois. There, “ she would talk politics with her father, defending the revolutionary's approach to social ills.”

The main house on the Oughton estate, a 20-room Victorian mansion, was built by Oughton’s father’s grandfather. Formally known as the John R. Oughton House, it was placed on the national historic register in 1980. Despite forty years of encroaching development since Oughton’s death, aerial photos show the Oughton estate (103 South Street) with a small lake in the middle and a thick ring of trees around it very much like the estate in Dreams.

The carriage house, in which Diana lived as a child, now serves as a public library. It may have already seemed like one when Ayers visited, an impression that finds its way into Dreams as a library “ filled with old books and pictures of the famous people [the grandfather] had known.”

I should caution that the analysis I have just offered, according to Remnick at least, is “mere twinkling in the Web’s farthest lunatic orbit.” In the complacently flat earth that Remnick inhabits, I am a “little-known conservative writer” with a racist axe to grind, and Christopher Andersen, despite his many bestsellers, does not exist.

On this and even weightier subjects, Remnick would rather you content yourself with his interpretation, which is often no interpretation at all.

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Editor's note: For a more complete account of this phenomenon, read Jack Cashill's amazing new book, "Hoodwinked: How Intellectual Hucksters Have Hijacked American Culture.


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