Did Barack Obama Almost Marry Another Woman Before Michelle?
It's almost unfathomable to think of Barack and Michelle Obama being with other people, but if circumstances had been different, Michelle wouldn't have been a First Lady.
Before meeting Michelle, Barack had his fair share of exes. In David Maraniss' biography, "Barack Obama: The Story," he detailed how Barack once dated Alex McNear, whom he met at Occidental College and shared his love for art and literature. Their relationship fizzled out when Barack moved to New York to study at Columbia, although the two exchanged passionate love letters when they were trying to make things work long-distance. In Columbia, he would later meet Genevieve Cook, a woman three years his senior who worked as a teacher. They dated for around 18 months, but it was mostly one-sided. "When she told him that she loved him, his response was not 'I love you, too' but 'thank you" — as though he appreciated that someone loved him," Maraniss wrote.
And then came Sheila Miyoshi Jager, who's known to be Barack's greatest love before Michelle. In Barack's book "Dreams from My Father," he described their relationship as "hidden and warm. Your own language. Your own customs. That's how it was." While he didn't divulge any more detail, nor did he even name her, historian David Garrow's "Rising Star: The Making of Barack Obama" biography made the revelation that Barack asked her to marry him.
Barack Obama proposed to his ex-girlfriend, Sheila Miyoshi Jager — twice
In "Rising Star: The Making of Barack Obama," David Garrow supplied more information about Sheila Miyoshi Jager that Barack failed to provide in his memoir. Jager corroborated Barack's assertion that they indeed had their own world when they were together. They started dating in 1986 and had "an island unto ourselves," she told Garrow. As recounted by the New York Post, the pair soon discussed marriage, and when the two visited Jager's family, Barack got down on one knee.
But Jager told him "not yet," partly because her parents thought she was too young and also because Barack butted heads with her father, who had opposing views in politics. A year into the relationship, however, something in Barack had changed. Jager told Garrow that his ambitions to become president suddenly intensified. It also dawned on him that to pursue those dreams, "he had to fully identify as African American," and he couldn't do that while dating someone White, which Jager is. At the time, Jager claimed that Barack "felt trapped between the woman he loved and the destiny he knew was his."
Barack eventually had to leave for Harvard at a time when their relationship was hanging by a thread. He proposed to her once more, but Jager thought it was "out of a sense of desperation over our eventual parting and not in any real faith in our future." She was bound to head to Seoul then — and felt frustrated over his assumption that she would drop her career for him. That became the tipping point, leading to their eventual split.
Barack continued to keep in touch with Sheila after meeting Michelle
After his first year at Harvard Law, Barack Obama signed up to be an associate at Sidley & Austin, a prestigious law firm. It was there he met Michelle Robinson, who we now know as Mrs. Michelle Obama. "Because I went to Harvard and he went to Harvard, and the firm thought, 'Oh, we'll hook these two people up,'" Michelle told ABC News when they assigned her to be his mentor. In his book "A Promised Land," Barack wrote that he "was smitten almost from the second I saw her," so he didn't hesitate to ask her out. Despite Michelle initially finding it "tacky" since they were colleagues, she eventually agreed.
As Barack and Michelle's relationship grew more serious, Sheila Miyoshi Jager returned to Barack's life. She, too, found herself at Harvard to teach, and per David Garrow, the former lovebirds "continued to see each other irregularly throughout the 1990-91 academic year, notwithstanding the deepening of Barack's relationship with Michelle Robinson." Jager confessed to feeling "bad about it," but nothing came out of it anyway. Barack and Michelle eventually tied the knot in 1992, effectively severing all ties with Jager, save for a letter or a phone call here and there.
With Michelle, Barack found his match. "Obviously I couldn't have done anything that I've done without Michelle," he told Oprah in 2011. "She is just my rock. I count on her in so many ways every single day."