Obama's Ambition Ruined His Romance With Woman He Proposed To Before Michelle

Before Barack Obama married Michelle, the 44th President of the United States had experienced some other significant romantic relationships. However, even as far back as his 1995 memoir, "Dreams from My Father," Obama was reluctant to discuss these individuals in detail. "I was very sensitive in my book not to write about my girlfriends, partly out of respect for them," Obama later explained to biographer David Maraniss (via Politico). Obama went even further and combined situations from different relationships, a strategy he called "compression."

In 2017, historian David Garrow separated details of those past romances in his 1,400+ page Obama biography, "Rising Star." Garrow located Sheila Miyoshi Jager, a woman Obama had proposed to twice before meeting Michelle.  Obama and Jager had a three-year romance in the 1980s when Jager was a University of Chicago doctoral student in anthropology. Obama was a community organizer who aspired to a political career, like the Mayor of Chicago or a national political office.  For Jager, who was living with Obama, his shift in mindset was abrupt. "He became ... so very ambitious very suddenly," she explained to Garrow (via The Washington Post). "By 1987, about a year into our relationship, he already had his sights on becoming president."

"Rising Star" claims Obama believed that to reach his career goal, he needed to emphasize his African American heritage. Discussions of race and Obama's and Jager's differing viewpoints complicated their relationship, impacting their decision to split up.

Even before Barack Obama set his sights on the presidency, there were conflicts in his relationship with Sheila Miyoshi Jager. In 1986, Obama proposed to Jager while the couple visited her family. Jager turned him down after her parents expressed doubts about Obama's career and said she was too young. Jager later explained to Garrow that as Obama's career goals became clear, their bond was overshadowed by his "torment over this central issue of his life . . . race and identity," (via The Washington Post). In "Rising Star," one of Obama's friends told David Garrow that the former president said, "If I am going out with a white woman, I have no standing here." Garrow also references the political difficulties experienced by two African American U.S. senators from Illinois with interracial marriages.

Obama's "Dreams from My Father" describes a scene with an unnamed girlfriend in which they have irreconcilable outlooks after seeing a play by an African American playwright. Jager recalled a different argument that caused a major rift, as she was upset that Obama wouldn't take a stand against a Chicago mayoral aide who had been making antisemitic remarks. 

Obama proposed to Jager the second time just as he was leaving for Harvard Law School and Jager was traveling to South Korea for her dissertation. She turned him down again, believing he was motivated by their impending separation rather than a desire for commitment.

In June 1989, after Sheila Miyoshi Jager and Barack Obama went their separate ways, Obama met his future wife when he took a summer job at a Chicago law firm. The then-Michelle Robinson was his mentor, and soon they began dating. Six months later, they were contemplating marriage. Then, at the beginning of 1990, Jager returned to the U.S. and accepted a Harvard teaching fellowship. While she was in South Korea, she and Obama had exchanged letters, so she was aware of his evolving relationship with Michelle. According to David Garrow's "Rising Star," once Jager and Obama were both at Harvard, the former couple occasionally met up. 

While the book doesn't specify what happened during Jager and Obama's interactions, Jager later told the author that it was a source of conflict for her. After a year of these get-togethers, their relationship definitively ended when Jager began a new romance with Jiyul Kim. The couple would eventually marry and have three children.  "As much as I loved [Obama], I was relieved when our paths finally parted," she recalled to Garrow, per People. Months later, Obama and Michelle got engaged.

After their marriages, Jager and Obama rarely corresponded. On September 1, 2001, Jager's husband was serving as a Colonel and was working at the Pentagon, and Obama contacted his former girlfriend after the 9/11 attacks.  In another instance, Obama called Jager to inquire if a biographer had communicated with her.