Gossip, News, President Obama

Meet the Woman Barack Obama Reportedly Proposed to Before Michelle?

Barack Obama clearly ended up with the right woman, but with news of his preMichelle marriage proposal making headlines, our curiosity about Sheila Miyoshi Jager was piqued.

In Rising Star: The Making of Barack Obama, Jager told Pulitzer Prize-winning biographer David J. Garrow that she had been seriously involved with the future president in the mid- to late ’80s and early ’90s. Not only did they move in together, but he proposed marriage — twice.

However, Obama’s political ambitions reportedly did them in; a mutual friend of the couple recounted that Obama explained that “the lines are very clearly drawn: If I am going out with a white woman, I have no standing here.” (For the record, Jager is of Dutch and Japanese ancestry.) Garrow wrote that Obama “felt trapped between the woman he loved and the destiny he knew was his,” implying that race factored into the Chicago politico’s decision to settle down with Michelle.

According to the book, Jager met Obama in the mid-’80s while doing community organizing in Chicago. Things turned romantic and they moved in together.

“In the winter of ’86, when we visited my parents, he asked me to marry him,” Jager, 53, recalled. She said that she turned down his proposal not for racial reasons but because her parents were concerned about Obama’s professional prospects and thought that Jager, then 23, was too young. (On the issue of race, a close family friend of Jager’s parents said that Obama came across to them like “a white, middle-class kid.”)


26 thoughts on “Meet the Woman Barack Obama Reportedly Proposed to Before Michelle?”

  1. He broke up with her because he knew the black people in Illinois would never elect him if he had a white wife.


  2. He ended up marrying Michelle to appeal to his “black side” but the guy did NOTHING for the African American community in his 8 years in office.


  3. This really isn’t news…almost everyone “could of” ended up with someone else. Funny, they painted Obama as “a typical white kid”. To me he was always whitewashed…more white than black, I’m speaking politically.


  4. Obama knew that playing on his Black heritage would get him a lot further than focusing on his White heritage. Obviously, this choice paid off for him.


  5. I like how he asked her to marry him twice, then when rejected twice. They act like he had a choice between michelle and her. No she didn’t want him. That is why he married someone else, not because he choose michelle for political purposes or who was prettier or smarter or ended up with the right one. This women clearly didn’t want to marry barry.


  6. This may not be a nice or politically correct thing to say, but he probably never would have been president if he was married to Jager. There are a lot of people out there (both white and black) who wouldn’t vote for a black man married to a white woman.


      1. Mr and Mrs. Obama have too much chemistry for him to be marrying her just for political gains so I’m going to need that lady to have several seats.


  7. Prez Obama married Michelle because he loved her and dumped the sprite because he didn’t want her, PERIOD.


  8. I’m confused on the one hand she says Obama was hell bent on marrying a black woman yet on the other hand she is claiming he proposed to her a white woman twice . Which is it ?
    White people and women in particular just feel that they are entitled to the best of everything even black people. FOH


  9. FUCK outta here. OF COURSE Obama had to marry a black woman, that’s politics and HELL NO he wouldn’t have been voted in if his wife was white!


    1. Seriously? How about we don’t know anything about Obama and his love life and we are speculating based off the media and their attempts to sell gossip!! People are always trying to bring negativity into black power couples relationships. So what if he dated a white women and almost married her! Key words “almost”.It seems to me that their relationship is genuine and that they have a great bond and a beautiful family!

      Liked by 1 person

      1. Agreed.
        Black folks would not have supported Obama if his wife were white, Hispanic, Indian, Asian, or biracial. He did not date black women before his wife and that was not a good look to run on a platform of first black president.
        Black community support of Obama was not support of him as an individual rather it was contingent on his identifying only as black and his marrying a black woman.


  10. Yeah well…, he and Michelle have too much chemistry to believe this bullshit….oh well y’all know the saying “once you go black you neva go back!!”


  11. These are all lies. The white women is the one, who told him to marry a strong black women, because he wanted to be a politican. It paid off for the first family. Good job Obama’s!


  12. The news that former President Barack Obama asked a Caucasian woman to marry him before he met Michelle Obama.
    Yeah like eight year old news.
    BTW people marry their parents and Obama’s mother was white so it wouldn’t have been a surprise if he had married a white chick.


  13. Not many of us married our child hood or high school sweetheart. So again, why is this important? Because she is not black? That’s the only thing you guys can dig up, is this the scandal?


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