This chapter critically engages Assata: An Autobiography by former Black Liberation Army operative and political exile Assata Shakur. The argument examines how Shakur develops psychologically and politically as both a Black revolutionary and a Black revolutionary woman. The chapter offers close readings of the political messages shared throughout Assata then contextualizes Shakur’s frameworks by turning to her experiences as a runaway teen in the Village in New York City. Her story – from childhood until her time being held as a political prisoner – compels attention to how blackness and gender collide and at times collapse. This chapter illustrates how her political communiqué “To My People,” broadcast by Shakur while incarcerated, was informed by the lessons on Black gender and sexual vulnerability she learned from Miss Shirley, a transgender woman who was her surrogate caregiver during her time living in the Village.