On August 22, 1860, an enslaved woman from Mississippi named Eliza Winston petitioned for her freedom before a judge in Minnesota?and she won. After she left the state for Canada, the abolitionists who helped her escape her enslavers told and retold the story, emphasizing their own actions; their detractors claimed they had used Winston as a pawn. Historians' accounts emphasize the mobs who battled in the streets after the ruling and the implications of the events for Minnesota politics. Winston is often portrayed as a simple woman, ignorant of the significance of freedom and needing to be convinced to pursue liberation. For more than 150 years, this is how Eliza Winston's story has been told.

In this a remarkable work, historian Christopher P. Lehman uncovers the story of Winston's first forty-two years and her long struggle to obtain her freedom. She was sold away from her birth family; her husband, a free man, died before he could purchase her freedom. She was enslaved in Tennessee, Louisiana, Kentucky, Mississippi, and Minnesota. At one time, a sitting US president?Andrew Jackson?bought her, and that purchase kept her enslaved by his relatives for over a quarter of a century.

The lives of individual enslaved people are almost entirely undocumented and untold. In Lehman's telling, Winston reappears as a capable, mature woman who understood her life and her values. Eliza Winston herself made the bold decision to leave behind everything she had known for an uncertain but free future.