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.”
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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.
