“Before Michelle” The Woman Who Almost Became Mrs. Obama

Barack Obama’s path to the presidency was filled with twists and turns, and before Michelle Obama, another woman played a significant role in his life. Her name was Sheila Miyoshi Jager. Obama and Jager met in Chicago when he was a community organizer, and they quickly fell in love. Jager, now a professor at Oberlin College, was a pivotal part of Obama’s life during those formative years.

“In the winter of ’86, when we visited my parents, he asked me to marry him,” Jager told David J. Garrow, author of Rising Star: The Making of Barack Obama. She replied, “Not yet,” thinking they were too young to tie the knot, but they stayed together. Their relationship was intense and somewhat insular, as Obama kept his work life separate from his personal life.

Jager didn’t meet many of his colleagues or the influential pastor, Jeremiah Wright. Things began to shift in 1987, about a year into their relationship. Jager noticed Obama becoming increasingly ambitious. She told Garrow, “I remember very clearly when this transformation happened, and I remember very specifically that by 1987, about a year into our relationship, he already had his sights on becoming president,” as reported by The Washington Post.

Obama’s growing ambition seemingly caused a strain in their relationship, and he started considering how his choices might affect his political future. In Chicago, some believed a non-African American spouse could hinder a black politician’s career. Race and identity became significant issues for the couple, leading to frequent arguments. A friend recalled Obama saying, “The lines are very clearly drawn… If I am going out with a white woman, I have no standing here.” Obama felt torn between his love for Jager and his political aspirations.

Just before leaving for Harvard Law School, Obama asked Jager to marry him again, but it didn’t feel right to her. She was planning to go to Korea for research and didn’t want to put her career on hold. They eventually parted ways, but their story didn’t end there. At Harvard, Obama became a star, elected as the first black president of the Harvard Law Review, which brought him national attention. However, some classmates found him annoying in class, even creating an “Obamanometer” to measure how pretentious his comments were.

Obama met Michelle Robinson at a law firm in Chicago after his first year of law school. They began dating seriously, but Jager wasn’t completely out of the picture. Garrow writes that Obama and Jager “continued to see each other irregularly throughout the 1990-91 academic year, notwithstanding the deepening of Barack’s relationship with Michelle Robinson,” as reported by The New York Post.

Obama and Michelle eventually married, but he maintained occasional contact with Jager, sometimes writing her letters or calling her. The journey from Sheila Miyoshi Jager to Michelle Obama shows the complex interplay of love, ambition, and identity that shaped Barack Obama’s early years and his path to the presidency.