It’s almost unimaginable to envision Barack and Michelle Obama with different partners, yet circumstances could have led to a different outcome for Michelle’s role as First Lady.
Before meeting Michelle, Barack had his share of previous relationships. In David Maraniss’ biography, “Barack Obama: The Story,” it was revealed that Barack once dated Alex McNear, whom he met at Occidental College. They shared a mutual love for art and literature, but their romance ended when Barack relocated to New York for his studies at Columbia. Despite attempts to sustain a long-distance relationship, it ultimately faded. Later in Columbia, he crossed paths with Genevieve Cook, a woman three years his senior and a teacher. Their relationship lasted roughly 18 months, though it was primarily one-sided. Maraniss noted that when she expressed her love for him, his response was not ‘I love you, too,’ but rather a ‘thank you,’ indicating an appreciation for her affection.
Then there was Sheila Miyoshi Jager, often considered Barack’s most significant love before Michelle. In Barack’s book “Dreams from My Father,” he characterized their relationship as “intimate and special. A world of our own. That’s how it felt.” While he didn’t offer further details and didn’t mention her by name, historian David Garrow’s biography “Rising Star: The Making of Barack Obama” revealed that Barack proposed to her.
In Garrow’s account, Sheila Miyoshi Jager provided additional insights that Barack omitted from his memoir. Jager confirmed that they indeed had their own universe when they were together. Their relationship began in 1986, and they created a space that was uniquely theirs. As reported by the New York Post, marriage discussions arose, and during a visit to Jager’s family, Barack even proposed on bended knee.
However, Jager asked him to wait, partly due to her parents’ belief that she was too young and partly because of conflicts between Barack and her father, who held differing political views. About a year into the relationship, something shifted within Barack. Jager explained to Garrow that his aspirations to become president suddenly took precedence. He also realized that to pursue these aspirations, “he had to fully identify as African American,” and he couldn’t do that while dating a white woman like Jager. At the time, Jager said that Barack felt torn between the woman he loved and the destiny he believed was his.
When Barack had to leave for Harvard, their relationship was already strained. He proposed to Jager once more, but she felt it was “out of a sense of desperation over our eventual parting and not in any real faith in our future.” She was on her way to Seoul at the time and was frustrated by his assumption that she would sacrifice her career for him. This marked the breaking point, leading to their eventual separation.
After his first year at Harvard Law, Barack joined the law firm Sidley & Austin, where he crossed paths with Michelle Robinson, now known as Michelle Obama. Assigned as his mentor, Michelle initially found the idea of dating a colleague “tacky,” but as Barack recalled in his book “A Promised Land,” he was captivated from the moment he laid eyes on her. He wasted no time in asking her out. Despite initial reservations, Michelle eventually agreed.
As Barack and Michelle’s relationship deepened, Sheila Miyoshi Jager re-entered Barack’s life. She, too, found herself at Harvard as a teacher, and according to David Garrow, the former flames “continued to see each other sporadically throughout the 1990-91 academic year, despite Barack’s deepening relationship with Michelle Robinson.” Jager admitted to feeling remorseful about it, but ultimately, nothing transpired. Barack and Michelle ultimately married in 1992, severing all ties with Jager, except for occasional letters or phone calls.
With Michelle, Barack found his true partner. In 2011, he expressed to Oprah, “Obviously I couldn’t have done anything that I’ve done without Michelle. She is just my rock. I count on her in so many ways every single day.”