Objective: This article explores the life and career of Sebastian K. Littmann. He was a foundational figure of the University of Calgary’s Department of Psychiatry in his role as its second chair and, before this, as an influential administrator at Toronto’s Queen Street Mental Health Centre and Clarke Institute during a transitional period in the 1970s-1980s. According to McGill University’s Heinz Lehmann, this transitional period was when the field of psychiatry underwent an identity crisis that threatened to dissolve the discipline and see its functions increasingly filled by counsellors, neurologists, and primary physicians. Littmann’s professional background and training in Edinburgh was followed by periods of community work in New York, which—by the time he immigrated to Canada—predisposed him to favour a humane and community-based approach to psychiatric work; this approach encompassed the cultural variations that were increasingly characterizing North America’s urban social landscape. His compassionate and progressive approach to treatment was remarkable in light of his troubled and deprived upbringing in Nazi-era Germany. Conclusions: The present sketch of Littmann’s personal and professional biography serves to highlight the ways that major historical events and large-scale migration movements, which affected Central Europe, impacted the development of Canadian psychiatry and, by extension, individual Canadians in the twentieth century.