This qualitative study utilized elite, semi-structured interviews of a purposive sample of the first women who became Special Agents and supervisors in the highly gendered Federal Bureau of Investigation (FBI). The historical context for their experiences is significant in light of social and legal mandates for equal opportunity and the increased interest in gender-specific research that took place during the 1970s. Literature relating to feminist perspectives, the integration of women into nontraditional occupations, and the gendered nature of bureaucracy supported the conceptual framework. Guided by educational criticism, four strategies were used recursively: typological analysis was used to define categories of data; interpretive analysis was used to identify patterns and connections in the data; evaluation was used to attach value to the data beyond the participants, and thematics were used to analyze pervasive messages within the data as a whole. Typologies included the choice of nontraditional careers, decision-making, efficacy as leaders, and efforts to negotiate the FBI’s bureaucracy. Three metaphors were used to interpret connections and patterns according to feminist standpoint theory, career self-efficacy theory, and various organizational principles. A Supergirl metaphor highlighted women’s unique knowledge and complex roles; a Target metaphor highlighted complex patterns for high achievement and response to obstacles, and a Clubhouse metaphor highlighted masculine culture, the role of rules, and changes to an organization’s equilibrium. Evaluation analysis addressed the moral obligation for women in leadership and the need for organizational diversity. Themes in the data included occupational pride, the challenge to manage multiple roles, an absence of relationship support, and inconsistency in feminist views.