This dissertation delves into the unique experiences of Black women principals in the Greater Boston Area. More precisely, it explores the impact of their distinctive leadership styles, characterized as either “unbought and unbossed,” a term originally coined by Congresswoman Shirley Chisholm, or a reinterpretation as “bought and unbossed.” The study investigates the success and challenges Black women encounter in the principalship while attempting to create a culture of achievement for Black students. This study explores the following questions: In what ways do Black women principals in the Greater Boston Area enact and embody “unbought and unbossed” leadership? What successes and challenges do Black women principals face? How do they navigate these challenges to ensure a culture of achievement for Black students? By adopting an inquiry stance and conducting 18 non-evaluative, semi-structured interviews, alongside a basic demographic and White supremacy culture survey, my research reveals profound insights into how Black women embody the essence of “unbought and unbossed” leadership. Furthermore, my research extends beyond Chisolm’s groundwork by introducing a new framework, “Principal-Ing While Black, Bought, & Unbossed: A Reframe of Shirley Chisholm’s Concept of Unbought & Unbossed Leadership.” This framework provides a deeper and more nuanced understanding of how the Black women in my study navigate the intricacies of their roles as principals in the Greater Boston area through a new term, “bought and unbossed leadership.” Through this framework, I construct a typology for the two leadership strategies, delving into their respective characteristics, methodologies, and, most importantly, the implications of their leadership on the individual, schools, and professions. By juxtaposing these concepts, I initiate a dialogue that illuminates the advantages and drawbacks associated with each approach to leadership by situating the examples in the lived experiences of the Black women in my study. This framework contributes significantly to the field of education as it positions Black women as experts on their own experiences and allows them to provide strategies developed by and for Black women to navigate the challenges of the principalship in urban districts.