Barack Obama Almost Married a White Woman, But Ambition and Race Got in the Way

The most recent biography of former President Barack Obama reveals a stunning story from his personal life: how race and political ambitions doomed a close relationship with a white woman Obama proposed to — twice! — before he married Michelle Robinson.

After Obama first proposed to Sheila Miyoshi Jager (now a professor at Oberlin College), continued "marriage discussions" were clouded by "torment over this central issue of his life ... race and identity," Jager told David J. Garrow for his book Rising Star: The Making of Barack Obama. "The resolution of his black identity was directly linked to his decision to pursue a political career."

Garrow added that Obama "felt trapped between the woman he loved and the destiny he knew was his." The future president reportedly believed he could not be the first black president and be married to a white (and part Asian) woman.

In the 2012 biography Barack Obama: The Story, David Maraniss recounts the community organizer's shifting identity — from multicultural and internationalist to distinctly African American. Garrow, as explained by The Washington Post's Carlos Lozada, puts that transition in political terms. Here's a particularly powerful passage from Lozada:

For black politicians in Chicago, he writes, a non-African-American spouse could be a liability. He cites the example of Richard H. Newhouse Jr., a legendary African American state senator in Illinois, who was married to a white woman and endured whispers that he “talks black but sleeps white.” And Carol Moseley Braun, who during the 1990s served Illinois as the first female African American U.S. senator and whose ex-husband was white, admitted that “an interracial marriage really restricts your political options.”

Jager, as a white girlfriend, represented a threat to Obama's political ambitions, and eventually the relationship ended. While she was virtually written out of Dreams From My Father, Obama's old girlfriend mentions two separate proposals in the new biography.

This close girlfriend might have reminded Obama of his own mother, Stanley Ann Dunham. Dunham studied anthropology with a focus on Indonesia, while Jager studied the same discipline but focused on the Korean Peninsula. In Obama's multicultural days, the two were "a natural pair."

"In the winter of '86, when we visited my parents, he asked me to marry him," Jager says in the book. Her parents opposed the match because they thought their daughter too young. Interestingly, they reportedly had no problem with the racial element — a close family friend said that Obama came across to them as "a white, middle-class kid."

In early 1987, Jager says she noticed a change. "He became ... so very ambitious. I remember very clearly when this transformation happened, and I remember very specifically that by 1987, about a year into our relationship, he already had his sights on becoming president."

Garrow writes that Obama believed he had a "calling," and that it was "coupled with a heightened awareness that to pursue it he had to fully identify as African American."

In this context, Obama may have consciously decided to avoid any appearance of "talking black but sleeping white."

A close mutual friend of the couple recalls Obama saying, "The lines are very clearly drawn. ... If I am going out with a white woman, I have no standing here."

Friends remember an awkward gathering at a summer house, when Obama and Jager engaged in a loud, messy fight for an entire afternoon. "That's wrong! That's wrong! That's not a reason," they recall hearing Jager yell from a guest room, with arguments punctuated by bouts of makeup sex.

Days before Obama would depart for Harvard Law School, the young man reportedly asked his girlfriend yet again to come with him and get married, Jager recalls. She adds that it was "mostly, I think, out of a sense of desperation over our eventual parting and not in any real faith in our future."

Jager was heading to Seoul for dissertation research, and she says she resented his assumption that she would postpone her career for his. While the couple went their separate ways then, it would not quite be the end of their relationship.

Barack Obama met Michelle Robinson at the Chicago firm where she worked after his first year of law school, and they quickly became serious. But Jager came to Harvard on a teaching fellowship at the time.

"Barack and Sheila [Jager] had continued to see each other irregularly throughout the 1990-91 academic year, notwithstanding the deepening of Barack's relationship with Michelle Robinson," Garrow explains. Once the Obamas got married, however, Barack's personal ties to Jager were reduced to the occasional letter and phone call.

"I always felt bad about it," the old girlfriend says in the book.

If Garrow's book is correct, that Obama allowed his political ambitions to shape his romantic decisions, it is truly ironic that Michelle Obama became very skeptical about his political prospects. She constantly discouraged his efforts toward elective office and resented the time he spent away from her and their daughters.

Barack reportedly vented to a friend about how often his wife would bring up the subject of money. "Why don't you go out and get a good job? You're a lawyer — you can make all the money we need," she told him, as the Obamas struggled with student loans and balancing family and political life.  According to Lozada, Garrow sides with Michelle, noting how Barack left his wife and newborn daughter Sasha for a meeting — the day after his second daughter was born.

Obama's racial and political self-identities seem inextricably linked, and his public persona may have cost him a great deal emotionally. Garrow memorably declares, "While the crucible of self-creation had produced an ironclad will, the vessel was hollow at its core."

Barack Obama may not have sold his soul for political ambition, but it seems he sold his heart. And the racial tensions which characterized the last years of his presidency made their first appearance in his personal life.