Before Michelle, Barack Obama Proposed To A White Woman

Before Michelle, Barack Obama dated a white woman named Sheila Miyoshi Jager. He even proposed to her — twice. But Sheila turned him down, and Obama thought having a black spouse would be better for his political ambitions anyway. A new biography by David Garrow, Rising Star tells the story.

Friendly meet-n-greet during an innovative & elegant book presentation researched by Dr. Sheila Miyoshi Jager. Presentación, Brothers At War pic.twitter.com/S1cYmtvVYB

— Jomara Álvarez Águila (@JomaraAlvarez) November 8, 2016

In 1985, after finishing school at Columbia University in New York, Obama moved to Chicago and worked as a community organizer. Much has been written about Obama’s time in Chicago, and how it formed and crystallized his beliefs as a person and as a politician. Obama himself talked at length about the experience in a memoir he wrote 10 years later, Dreams of my Father.

“It wasn’t until I moved to Chicago and became a community organizer that I think I really grew into myself in terms of my identity.”

While there, Obama connected directly with the African-American community in a way he had not experienced before and achieved considerable professional success through his fundraising efforts and community outreach programs.

He also met a woman, Sheila Miyoshi Jager. Sheila is mixed-race, of Dutch and Japanese ancestry, with dark hair, light skin, and slight frame.

#obama first love? Sheila Miyoshi Jager, a grad student (now professor) who Obama lived with & proposed to TWICE. https://t.co/ul4RILLWSF pic.twitter.com/DRAXuFIR3l

— 78tiger (@78tiger) May 3, 2017

Obama, who was raised by his white mother and her family, had long experienced the difficulties that come from growing up mixed race. The complications that come from straddling two cultures has been detailed in his books and biographies. In Rising Star, Garrow hypothesizes that Sheila represented the multicultural world that Obama came from.

Like Obama’s mother, Sheila studied anthropology. She was educated, pursuing a doctorate at the University of Chicago. She was white. And she understood what it was like to grow up between two worlds.

In 1986 the couple visited her parents, and he proposed. Sheila’s mother thought she was too young to get married, so the couple decided to wait a little longer.

It was not long after that that Sheila sensed a shift. Obama supposedly became very ambitious and began to talk seriously about becoming president.

“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.”

He also became more aware of the status of race in America, and reportedly felt that he would have to fully identify as African American to be successful in politics. Garrow writes that Obama shifted from viewing himself as multicultural to distinctly African American. He cited examples of the difficulty having a white spouse posed for black candidates, quoting black politicians in interracial marriages or relationships who noticed controversy surrounding their personal relationship in this manner.

Garrow interviewed Sheila for his book, and she spoke freely about fights the couple had concerning marriage. It seemed that although Obama was keenly aware of his decision not to enter into an interracial marriage, he was also reluctant to hurt Sheila and did not want to break things off.

Then, Obama was accepted to Harvard Law School. Sheila herself had plans to travel to Seoul, South Korea, for academic research. This would have been an easy time to end the relationship.

Instead, Obama asked — for a second time — if she would marry him.

Sheila said no. She felt he asked her more because he was sad about their impending breakup than because he really wanted to marry her, and she also resented the assumption that she would postpone her career for his. The couple had a fight and broke up.

They stayed in touch with letters and even met up a few more times, but Barack — and history — followed a different path.

In 1989, Barack Obama met Michelle, the woman he would later marry.

[Featured Image by Scott Olson/Getty Images]