Deconstructing Obama: The Life, Loves, and Letters of America's First Postmodern President

by Jack Cashill

  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 Geiser 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.” Writes Ayers of Oughton in Fugitive Days, “She had been to the manor born—the oldest of four sisters, she was raised in rural Illinois, her father a kind of gentleman farmer from a previous age.”

  Ayers knew this manor from experience. According to a Time article written soon after her death, Oughton “brought Bill Ayers and other radicals” to the family homestead in Dwight, Illinois. Oughton’s father’s grandfather built the main house on the estate, a twenty-room Victorian mansion. Formally known as the John R. Oughton House, it was placed on the national historic register in 1980. In this unlikely setting, Diana and her Weather pals would defend “the revolutionary’s approach to social ills” in discussions with her too-tolerant old man.

  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, Illinois, for those who wish to see—confirm, the estate has a small lake and, despite forty 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. “She knew other worlds and other languages and I knew nothing,” he writes; “she was sophisticated and I was simple, she was untouchable.” Although Ayers had come from a family of means himself, Oughton’s world intimidated him: “Diana’s whole story was written on her face, etched with every advantage, accented with privilege.” She awed him as she attracted him. “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’s 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’s 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. In Dreams, Obama worries that his world would inevitably yield to his girlfriend’s. “I knew that if we stayed together,” he writes, “I’d eventually live in hers.” In Fugitive Days, Ayers describes how seductive the world of the Oughtons could be: “a perfect marriage, a comfortable career in banking, say, or the law, two golden children, the clubs, the country home.”

  Despite his obsession with Oughton, Ayers had other lovers, but then again, so did Oughton. This troubled Ayers considerably. He does not say whether this led to their parting, but he was not with her at the end. When Obama says, “I pushed her away,” one has to wonder if we are really hearing Ayers. This 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.” That death continues to haunt Ayers and almost assuredly found an outlet in Dreams, written six years before his own memoir.

  “Whenever I think back to what my friend said to me, that night outside the theater, it somehow makes me ashamed,” an unsmiling Obama tells Auma, while cutting “green peppers.” In his 1997 book, A Kind and Just Parent, Ayers specifically links “green peppers” with “saltpeter” and other “mysterious drugs in the food” that scare young men with the threat of impotence. Go figure.

  Remnick concedes that Dreams is not to be taken at face value. 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, Remnick has conspicuously little to say. The reader of The Bridge would not know Obama had such a relationship if Remnick had not mentioned it casually in his later discussion of Dreams as a book.

  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, re-creation, 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’s contrivance. As to why Obama would need to invent a girlfriend, I will come to that soon enough.

  Long before Obama meets Michelle, he meets “Regina” from Chicago’s South Side. Obama describes her as “a big, dark woman who wore stockings and dresses that looked homemade.” And although Obama has no romantic interest in Regina, Remnick rightly describes her as a “harbinger” of Michelle, more literary device than flesh-and-blood woman. It is she who sets him on his journey to find his inner African American and rather forcefully at that.

  “Her voice,” Obama writes, “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.” The home life that Regina describes—“evenings in the kitchen with uncles and cousins and grandparents, the stew of voices bubbling up in laughter”—proves a powerful lure for Obama.

  In Dreams, it is Regina who convinces Obama to abandon the name Barry. “Do you mind if I call you Barack?” she asks. “Not as long as you say it right,” he answers. Coming straight from the motherland, Barack Sr. pronounced his name “BARR-ick,” not “buh-ROCK.” Barack Sr. himself was known as “Barry” when he was in Hawaii. When Obama visits Africa, well after he has become “Barack,” all of his kin call him “Barry.” It is Obama who will insist on saying the name wrong, perhaps strategically. This rebranding would actually help pave his way to the presidency.

  Not until the very end of Dreams does Obama find Michelle and the fulfillment implicit in Regina’s vision. As described in Audacity, her kitchen sounds suspiciously like Regina’s—“uncles and aunts and cousins everywhere, stopping by to sit around the kitchen table and eat until they burst and tell wild stories and listen to Grandpa’s old jazz collection and laugh deep into the night.”

  Like so much in his life, his choice of a church, for instance, Obama’s selection of Michelle is fragrant with calculation, not only on an emotional level but also on a political level. Remnick more than hints at this. A black campaign worker in South Carolina tells him that Obama’s selection of a black wife, particularly a dark-skinned one, “matters to people here.” Princeton political scientist Melissa Harris-Lacewell, a black female who had attended Obama’s church, elaborates: “I don’t think Obama could have been elected President
if he had married a white woman.” She adds, “Had he married a white woman, he would have signaled that he had chosen whiteness.”

  At the height of the Reverend Wright controversy, Obama played his Michelle trump card. “I am married to a black American who carries within her the blood of slaves and slaveowners,” he boasted in his bellwether speech on race, “an inheritance we pass on to our two precious daughters.”

  Dreams culminates in Obama’s wedding to Michelle. As with all previous relationships, this tale of courtship is strikingly devoid of any reference to love, sex, or romance. At his most passionate, Obama says of Michelle, “In her eminent practicality and Midwestern attitudes, she reminds me not a little of Toot [his grandmother].” That description must surely have warmed the cockles of Michelle’s heart.

  In Audacity, Obama does not even get the date of their first meeting right. “I met Michelle in the summer of 1988,” he writes, “while we were both working at Sidley & Austin.” Obama acknowledges he had just finished his first year at law school, but he did not begin Harvard Law until the fall of 1988. As shall be seen, there are some serious date manipulations in the Obama narrative. This is not one of them. This is what happens when other people write your books.

  WINE-DARK SEA

  I had underestimated Obama’s muse. At first glance, I had thought the mystery girlfriend on the large estate a gratuitous imposition. On first reading, I had seen in Dreams’ many nautical references the muse’s sea-stained fingerprints, indifferently applied. And then the lightbulb flicked on. Of course, the muse had taken Obama’s ungainly, bloated manuscript and infused it with the structure and spirit of Homer’s Odyssey. The nautical imagery, the mystery girlfriend, and many more of the book’s inventions serve a purpose.

  On December 28, 2008, I published a piece in American Thinker on this subject. I argued that in Dreams Obama “assumes the role of both Telemachus and Odysseus, the son seeking the father, and the father seeking home.” Having spent two full years of high school Greek classes reading the Odyssey, I wondered, however, if I had not unwittingly wielded “Maslow’s hammer.” Said psychologist Abraham Maslow some years back, “It is tempting, if the only tool you have is a hammer, to treat everything as if it were a nail.”

  If I needed validation, I got it three weeks later in the New York Times. The paper’s Pulitzer Prize–winning literary critic, Michiko Kakutani, described Dreams almost exactly as I had: “a quest in which [Obama] cast himself as both a Telemachus in search of his father and an Odysseus in search of a home.” I seriously doubt if Ms. Kakutani purloined my thesis, especially given her conclusion that Dreams was “the most evocative, lyrical and candid autobiography written by a future president.” She apparently inferred the Homeric structure in reading the text, as did I.

  The Dreams muse leaves scarcely a Homeric trope unturned in his mining of the Odyssey to describe Obama’s “personal interior journey.” Before he completes his heroic cycle, Obama will confront green-eyed seductresses, Sirens, blind seers, lotus-eaters, the “ghosts” of the underworld, the God-guide Hermes, and about a half-dozen sundry “demons.” Only when I found a “menacing” one-eyed bald man, however, did I feel confident I had not hammered in vain. Menacing, by the way, is one of those words that Ayers likes: he uses it multiple times in every book. Even toy soldiers he describes as “menacing.”

  Early in Fugitive Days, Ayers tips his Homeric hand. “Memory sails out upon a murky sea—wine-dark, opaque, unfathomable,” he writes with a knowing wink. “Wine-dark” is quintessential Homer. Bestselling author Thomas Cahill named his book on ancient Greece Sailing the Wine-Dark Sea. It did not surprise me to learn that Cahill had attended my high school, but then again so had Weather Underground alum Brian Flanagan, who had taken the same Greek courses I did a year ahead of me. Ayers and pals may have been lunatics—Flanagan seems the sanest of the bunch—but they were literate ones.

  Dreams and the Odyssey both begin in medias res, a literary technique in which the narrative starts in mid-story and not from the literal beginning. Odysseus’s son, Telemachus, is twenty when the Odyssey begins. Obama has just turned twenty-one. Each saga begins with the young protagonist receiving an unexpected call that inspires him to seek out his missing father, Telemachus’s from Athena, Obama’s courtesy of Ma Bell.

  The structure of Dreams is more naturally chronological than the uneven Odyssey. After the opening sequence, Obama takes the reader back to his “Origins.” There he tells us that Barack Sr. quit the isle of Hawaii and abandoned his son for Harvard in Obama’s third year of life. (In reality, it was his first. More on this later.) Odysseus too had quit the isle of Ithaca and abandoned his son to fight in the Trojan War in Telemachus’s first year of life.

  As a former merchant seaman, Ayers often thought in terms of charts and maps when plotting life’s journey. In Fugitive Days, he yearns for a “mariner’s chart of the past” to help navigate, but he knows there is no such thing. He and his colleagues must face every day “as free people with neither road maps nor guarantees.” In A Kind and Just Parent, he writes of a friend, “the geography of his life was mapped around hard work, family and faith.”

  Obama uses the imagery of maps and charts much as Ayers does. In the introduction of Dreams, Obama talks of the book he had originally intended to write, a prosaic analysis of race and law. He describes it as “an intellectual journey that I imagined for myself, complete with maps and restpoints and a strict itinerary.” He changed his mind, of course, and settled on “a record of a personal, interior journey—a boy’s search for his father, and through that search a workable meaning for his life as a black American.”

  As Obama becomes aware of his blackness, he begins “to see a new map of the world, one that was frightening in its simplicity, suffocating in its implications.” He traces the map’s origins back to the day, centuries earlier, when “blind hunger” drove the white man to land on Africa’s shores. “That first encounter had redrawn the map of black life,” Obama argues. In Race Course, Ayers speaks of “the map of my life, already drawn.”

  When Obama leaves Hawaii for college in Los Angeles, he leaves his white mother and grandparents “at some uncharted border.” Aware now of his blackness and their whiteness, he feels “utterly alone,” not unlike the “utter loneliness” that Ayers felt upon setting off on his own. From this point on, Obama himself will be responsible for “charting his way through the world.” He and Ayers both describe this world as “uncertain.” Like Odysseus, he feels himself “unanchored to place.” He adds, “What I needed was a community.” Obama’s effort to locate that community in black Chicago, like Odysseus’s effort to regain his troubled Ithaca home, is fraught with peril and temptation, some of it factual, some of it finessed from facts, some of it fully invented.

  Obama is not the first writer to see Hawaii as the land of the lotus-eaters. “Junkie. Pothead,” he writes in retrospect of the experience. “That’s where I’d been headed: the final, fatal role of the young would-be black man.” In Los Angeles, change comes slowly. Finding his way as a black man, he resists the allure of his own Calypso figure, the “good-looking” Joyce. This Occidental College co-ed tries to lure him from his quest for black self-fulfillment with the worldly equivalent of immortality, namely assimilation and “multiracial” anonymity. Despite her “honey skin and pouty lips,” Obama resists the “gravitational pull” of her postracial promise.

  While still in Los Angeles, Obama finds his own private Cyclops in a college library “whose boundaries,” Rod Serling might have said, “are that of imagination.” The Cyclops in question is actually an Iranian student, an “older balding man with a glass eye.” He sits across from Obama and a black friend and, for no good reason, chides them about the failure of American slaves to rebel in any meaningful way. Obama’s friend falls strangely mute before the Iranian’s “menacing look,” but Obama leaps to the slaves’ defense.

  “They did fight. Nat Turner, Denmark Vescey [sic],” snaps Obama.
He adds, “Was the collaboration of some slaves any different than the silence of some Iranians who stood by and did nothing as Savak thugs murdered and tortured opponents of the Shah?”

  This conversation allegedly takes place in early 1980, a few heated months after fifty-two Americans were taken hostage in the newly Islamic Iran. If Obama were still focusing his anti-Iranian wrath on the Shah and Savak, he was one of only about a half-dozen Americans so inclined. I suspect Ayers inserted the scene to strengthen the Homeric theme and settle an old score with the American-friendly Shah. By the way, in Fugitive Days Ayers cites “Nat Turner’s uprising, Denmark Vesey’s revolt” as positive examples of democratic action. Writing in 2001, three years into the Google era, he even gets the spelling of “Vesey” right.

  Obama leaves Los Angeles for Columbia a year later. To make the brooding Telemachus imagery work, Obama had to scrub one person out of the record, Occidental friend Phil Boerner. Boerner transferred with Obama to Columbia and roomed with him his first year in New York. There is no mention of a character anything like him in Dreams. A registered Democrat and Obama fan, Boerner conveniently lay low until well after the 2008 election. It seems likely that he was told to. Wrote Boerner in January 2009:

  I remember often eating breakfast with Barack at Tom’s Restaurant on Broadway. Occasionally we went to The West End for beers. We enjoyed exploring museums such as the Guggenheim, the Met and the American Museum of Natural History, and browsing in bookstores such as the Strand and the Barnes & Noble opposite Columbia. We both liked taking long walks down Broadway on a Sunday afternoon, and listening to the silence of Central Park after a big snow. I also remember jogging the loop around Central Park with Barack.