Barack Obama proposed to Sheila Jager before he ever met Michelle. A new book claims that race played a role in why it didn't work out.
Obama Michelle

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It’s hard to deny that Barack and Michelle Obama are adorable. (See evidence here, here, and here.)

And after nearly a decade as America’s first family, they are widely thought of as a package deal.

But in a revealing new book — Rising Star: The Making of Barack Obama — biographer David J. Garrow reports that Michelle was actually not the first woman for whom a young Obama got on bended knee.

That would be Sheila Miyoshi Jager — whose hand Obama asked for in 1986.

This surprising revelation has Americans wondering what it would have been like to have a different lady in the West Wing. Or, more cynically, if Obama would have made it there at all with a white woman on his arm.

He seems to have thought he wouldn’t have.

Jager, who is now a professor at Oberlin College, told Garrow that Obama had his sights set on the presidency long before his political career began. Garrow paints a portrait of a young Obama who felt that becoming America’s first black president was his destiny — one he would have to make personal changes and sacrifices to fulfill.

He realized, the book reads, “that to pursue it he had to fully identify as African American” — which meant an African-American spouse.

Sheila Jager

Oberlin CollegeSheila Jager

Jager, who lived with Obama and was a couple years his junior, remembers the future president’s “torment over this central issue of his life . . . race and identity,”

And a close mutual friend of the couple adds that “the lines are very clearly drawn. . . . If I am going out with a white woman, I have no standing here.”

Even so, the relationship persisted even as Obama’s ambitions were solidifying.

Obama been a community organizer in Chicago for most of their relationship. A few days before he left for Harvard, he asked Jager to marry him.

Jager, who had plans to study in Seoul, resented the idea that she should put Obama’s plans ahead of her own and sensed that he had only proposed “out of a sense of desperation over our eventual parting and not in any real faith in our future.”

So she said no.

Obama went to Boston without her, where he would excel in his classes and become the first African-American president of the Harvard Law Review.

The summer after his first year, he met a young Michelle Robinson. Soon after they began seriously dating, though, Jager arrived at Harvard for a teaching fellowship. The old flame was briefly rekindled, something Jager says she “always felt bad about.”

After Michelle and Barack were married in 1992, Jager only heard from him rarely; once in a letter after the 9/11 attacks, and once to see if a biographer had reached out to her.

Garrow never questions Obama’s commitment to and sincere love for Michelle, but he is highly critical of his subject.

He accuses Obama of constructing a persona for political purposes — lying about the extent of his cocaine use, showing a level of religious faith on the campaign trail that his friends hadn’t seen before, maybe even regulating his love life.

None of this is particularly damning as all politics requires some level of theatrics. The level of prescience demonstrated by Obama with regard to his own future and historical importance, though, is, at times, unsettling.

“The depth of this commitment may be summarily dismissed as the unfounded optimism of the average American,” Obama wrote more than 25 years ago. “I may not be Donald Trump now, but just you wait; if I don’t make it, my children will.”


Next, check out these 29 images and fun facts that show how cool, handsome, and bad ass some American presidents were as young men. Then take a look inside the life of a twenty-something Hillary Clinton.

Annie Garau
Annie is a NYC-based writer. For tips, write to [email protected].
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