Barack Obama Proposed to Someone Else Before Michelle, But Politics Changed His Destiny

Barack Obama's path to the presidency was filled with twists and turns. But before he met Michelle Obama, there was another woman who played a significant role in his life. Her name was Sheila Miyoshi Jager. Obama and Jager met in Chicago when he was a community organizer and they quickly fell in love. Jager, now a professor at Oberlin College, was a big part of Obama's life in those early years. "In the winter of '86, when we visited my parents, he asked me to marry him," Jager told David J. Garrow, the author of Rising Star: The Making of Barack Obama.

She replied, "Not yet," thinking they were too young to tie the knot, but they still stayed together. Their relationship was intense and they lived in their own little world. Obama kept his work life separate from his personal life. Jager didn't meet many of his colleagues or the influential pastor, Jeremiah Wright. Things changed in 1987, about a year into their relationship. Jager noticed Obama becoming very ambitious. She told Garrow, "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," as per The Washington Post. 

Obama's growing ambition seemingly caused problems, and he began to think about how his choices might affect his political future. In Chicago, some people thought a non-African American spouse could hurt a black politician's career. Race and identity became big issues for the couple as they argued about it a lot. A friend remembered Obama saying, "The lines are very clearly drawn... If I am going out with a white woman, I have no standing here." Obama felt torn between his love for Jager and his political dreams.

Just before Obama left for Harvard Law School, he asked Jager to marry him again but it didn't feel right to her. She was going to Korea for research and didn't want to put her career on hold. They went their separate ways, but it wasn't the end. At Harvard, Obama became a star; he was elected the first black president of the Harvard Law Review. This brought him national attention but some classmates found him annoying in class, even creating an 'Obamanometer' to measure how pretentious his comments were.

Obama met Michelle Robinson at a law firm in Chicago after his first year of law school. They started dating seriously but Jager still wasn't completely out of the picture. Garrow writes that Obama and Jager "continued to see each other irregularly throughout the 1990-91 academic year, notwithstanding the deepening of Barack's relationship with Michelle Robinson," as per The New York Post. Obama and Michelle got married, but he stayed in touch with Jager occasionally. He would write her letters or call her sometimes.