If the aphorism “history will be the judge” is deployed, the active agent of this formulation is the historian. Comparing two great(ly infamous) doctors, John C. Cutler and Alan Berkman, the article considers how historians balance digging for sources, creating meaningful narrative, and acknowledging our own beliefs that embed in the judgments we make. The article explores our responsibility for balance and moral judgment at the same time. Cutler, admonished for his role in the infamous sexually transmitted diseases studies in Tuskegee and Guatemala, also was a well-respected researcher and teacher. Berkman, renowned for his success in global HIV/AIDs activism, was also only the second physician in U.S. history to be charged with accessory to murder after the fact and who served seven hard years for bombings and robbery. The author considers her relationship to these physicians and the effort to create a passionate historical practice.