On October 17, 1882, Mary Booth, a fourteen-year-old African American girl, arrived at the Virginia State Penitentiary to serve a life sentence after being wrongfully convicted of murder. Working from a fragmented and fragmentary archival record, this article reconstructs the tortuous path Booth traveled through Virginia’s courts and prisons. Her story sheds light on how African American children were transformed into new carceral subjects in the wake of emancipation. It also provides insight into the varied strategies black Virginians employed in their efforts to extract meaningful, if inadequate, gains in access to justice under the Readjuster Party. Ultimately, locating Booth’s story within the larger history of children’s incarceration offers insight into why Virginia’s late-nineteenth-century juvenile justice reforms entrenched, rather than diminished, racial disparities for young citizens accused of crimes.