The current study proposed and tested a conceptual model of medical mistrust in a sample of African American men (N = 216) recruited primarily from barbershops in the Midwest and Southeast regions of the United States. Potential psychosocial correlates were grouped into background factors, masculine role identity/socialization factors, recent healthcare experiences, recent socioenvironmental experiences (e.g., discrimination), and healthcare system outcome expectations (e.g., perceived racism in healthcare). Direct and mediated relationships were assessed. Results from the hierarchical regression analyses suggest that perceived racism in healthcare was the most powerful correlate of medical mistrust even after controlling for other factors. Direct effects were found for age, masculine role identity, recent patient-physician interaction quality, and discrimination experiences. Also, perceived racism in healthcare mediated the relationship between discrimination experiences and medical mistrust. These findings suggest that African American men's mistrust of healthcare organizations is related to personal characteristics, previous negative social/healthcare experiences, and expectations of disparate treatment on the basis of race. These findings also imply that aspects of masculine role identity shape the tone of patient-physician interactions in ways that impede trust building processes.