Historians since the mid-1960s have debated how former slaves claimed freedom during and after the Civil War. This thesis examines the actions and behaviors of the enslaved leading up to and following emancipation as gendered expressions of freedom. Utilizing gender analysis of primary evidence --- including WPA interviews, narratives composed by former slaves, letters and petitions written by black soldiers, and government reports --- this thesis demonstrates how an understanding of freedom was described by men and women and the actions they took to reify it. By drawing on the work of psychologists such as Erik Erikson, Lawrence Kohlberg, Nancy Chodorow and Carol Gilligan this thesis considers how gendered expectations shaped an understanding of freedom and created a set of priorities necessary in making it a reality. An examination of the evidence demonstrates that formerly enslaved African American men engaged in freedom seeking behaviors focused on establishing an independent masculine identity while African American women engaged in freedom enacting behaviors directed towards maintaining their network of relationships. Furthermore, within this gender-based framework, the utilization of the post-structural theory of intersectionality shows that intragroup differences based on identity shaping factors created a multitude of nuanced differences in behaviors towards constructing a meaningful freedom.