This study examines how individuals make the decision to become police officers in the context of a police legitimacy crisis and how men and women’s decision-making processes may be different. In-depth interviews were conducted with 42 criminal justice college students who want to become police officers. Prospective police officers anticipated facing challenges as a direct result of the current climate surrounding American policing, which is characterized by decreased police legitimacy. On top of this, women anticipated facing more challenges than male officers due to their gender and underrepresentation in police work. However, women were uniquely motivated to enter policing to overcome gender-specific challenges and felt that they offered special skills that would provide solutions to the police legitimacy crisis. The paper draws implications for how agencies can identify more quality candidates and increase their representation of women.