The invented love life of Barack Obama

By Jack Cashill

On July 31, 2008, I first voiced my suspicions, here in the pages of WorldNetDaily, that Barack Obama had substantial help with the writing of his much acclaimed 1995 memoir, “Dreams from My Father.”

By September 2008, I was confident that this help had been provided by Obama’s friend and neighbor, Bill Ayers, a gifted writer and editor and the Brett Favre of terrorism, sidelined perhaps but forever itching to get back in the game.

The more I explored the question of authorship, however, the more I came to see a problem of at least equal gravity – namely, whether the story told in “Dreams” was true.

In my book to be released in February, “Deconstructing Obama,” I explore both issues in depth. What I will show is that the story Obama told over and over again on the campaign trail varies from the true story in ways big and small.

Let me focus here on one salient part of that story, Obama’s love life. In his all-consuming search for identity, his romances 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, but Obama gives the reader very close to nothing. “Cosby never got the girl on ‘I Spy,'” he laments in “Dreams,” but in his own retelling, he does not do much better.

In his 600-plus page Obama-friendly biography, “The Bridge,” David Remnick lays down the baseline of what the mainstream media know about the president – or at least what they want us to know.

Appreciate Jack Cashill’s investigative moxie? Check out one of his many books, “Hoodwinked: How Intellectual Hucksters Have Hijacked American Culture”

Where Remnick falls oddly silent – not even to hector the blogosphere, which he does often – is on the question of Obama’s amours.

As it happens, Obama spent 13 years as a single man on the mainland before he married Michelle in 1992 – 10 of those before he met her.

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, either in Remnick’s book or in any Obama biography.

In “Dreams,” Obama talks of his love life on only one occasion. When his half-sister Auma visits him in Chicago pre-Michelle, he tells Auma about a ruptured relationship with a white woman back in New York.

Obama 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 ladies.

Although he speaks of the white woman 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.”

This is no casual relationship. “We saw each other for almost a year. On the weekends, mostly. Sometimes in her apartment, sometimes in mine. You know how you can fall into your own private world? Just two people, hidden and warm. Your own language. Your own customs. That’s how it was.”

This nameless young woman had grown up on a sprawling estate in the country. It was during a visit to the country home that Obama began to see the distance between “our two worlds.” That distance ultimately leads to their separation. “I pushed her away,” Obama tells Auma ruefully.

An interracial romance should have been grist for an aspiring writer’s mill, especially a writer as obsessed with racial identity as Obama, but he gives this tale only a few paragraphs.

I was not the only one to have noticed Obama’s curious silence on this issue. One correspondent of mine made a compelling case that Obama’s mystery woman was drawn fully from the memory of Bill Ayers and based on the great love of Ayers’s life, the late Diana Oughton.

Ayers was obsessed with Oughton who died in 1970 in a Greenwich Village bomb-factory blast. In “Fugitive Days,” his 2001 memoir, he fixes on her in ways that had to discomfit the Weatherwoman he eventually settled for.

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, copies of which my correspondent sent me, 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. “The house was very old, her grandfather’s house,” Obama writes of his girlfriend’s country home. “He had inherited it from his grandfather.”

According to a Time magazine article written soon after Oughton’s death, Oughton had “brought Bill Ayers and other radicals” to the family homestead in Dwight, Ill. Oughton’s father’s grandfather built the main house on the estate, a 20-room Victorian mansion.

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 Obama’s words as a library “filled with old books and pictures of the famous people [the grandfather] had known – presidents, diplomats, industrialists.”

“It was autumn, beautiful, with woods all around us,” Obama writes of his visit to his girlfriend’s country home, “and we paddled a canoe across this round, icy lake full of small gold leaves that collected along the shore.”

As aerial photos of the Oughton estate (103 South Street, Dwight, Ill.) confirm, the estate has a small lake and, despite 40 years of encroaching development, is still thickly ringed by trees.

“I realized that our two worlds, my friend’s and mine, were as distant from each other as Kenya is from Germany,” says Obama of his girlfriend.

Ayers expressed similar anxieties about Oughton. “I adored her the moment I saw her,” he writes, “but I knew she was way beyond my reach – too mature, too smart, too experienced.”

In projecting Ayers’ sentiments, or so it appears, Obama suggests more than a metaphor when he describes how he and his girlfriend fell into their “own private world” where they were “just two people, hidden and warm.”

Ayers and Oughton shared a literal “hidden world,” one that functioned, in Ayers’ words, as “a parallel universe somewhere side by side with the open world.”

Again, Obama seems to be channeling Ayers when he relates how he and his friend developed their “own language,” their “own customs.”

Writes Ayers of Oughton and others in the underground, “We spoke in a language that was meaningless babble to outsiders.” He adds, “We invented words; we constructed culture.”

“Between the two of us,” Obama writes, “I was the one who knew how to live as an outsider.” This was a sensation that the fugitive Ayers – “nowhere a stranger but everywhere an outsider” – was fully capable of imagining and imparting.

When Obama says of his imagined girlfriend, “I pushed her away,” one has to wonder if we are really hearing Ayers. His own split with Oughton led one radical feminist in the underground, Jane Alpert, to chastise Ayers publicly “for his callous treatment and abandonment of Diana Oughton before her death.”

Unlike Remnick, Obama biographer Christopher Andersen made a serious effort to identify Obama’s mystery woman, but he failed. “No one,” he writes, “including [Obama’s] 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” – “a mixture of 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 a creation largely of Ayers’ contrivance. As to why Obama would need to invent a girlfriend, that is a question I do indeed tackle in the book.

Jack Cashill

Jack Cashill has a Ph.D. from Purdue University in American studies. His latest book is "Untenable: The True Story of White Ethnic Flight from America's Cities." Read more of Jack Cashill's articles here.