Before marrying Michelle Obama, Barack Obama was deeply involved with another woman, according to David J. Garrow’s biography Rising Star: The Making of Barack Obama. In his early 20s in Chicago, Obama dated Sheila Miyoshi Jager and even proposed to her twice.
The relationship ultimately ended as Obama’s political ambitions grew and he left for Harvard Law School. Jager later became a respected academic, while Obama went on to build the life and career that made him a global figure.
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