Between 1928 and 1953, Joseph Stalin was the undisputed totalitarian dictator of the former Soviet Union whose “reign of fear” continues to maintain its egregious reputation. An examination of Stalin’s documented behaviors attempts to evaluate any signs of psychopathology in accordance with DSM-IV-TR criteria. Evidence of a troubled upbringing, depression, paranoia, and alcohol abuse suggests psychopathology as an implicating factor behind Stalin’s actions. Utilizing such a perspective may allow for future distinctions of individuals deemed responsible for horrendous atrocities.