Barack Obama clearly ended up with the right woman, but with news of his pre–Michelle 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.”)