This chapter discusses Jane Bolin's career in the legal profession and the lived experiences that produced her as the nation's first African American woman judge. A member of a small unit of black women lawyers, Bolin's early practice mirrored that of other black women lawyers who gained entrance, but not full integration, into the legal profession. Jane's strides in the legal profession from 1931 to 1939 were made relatively quickly, suggesting a tale of easy access and an unobstructed path. However, an examination of her professional life beyond the pioneering peaks reveals the pervasive discrimination that Bolin overcame, and unravels the threads of gender, class, race, credentialism, and politics that colored the fabric of her professional life.