Robert (Bobby) James Fischer (1943–2008) remains one of the most puzzling and enigmatic personalities in modern American history. In 1972, at the height of Cold War tensions between the Soviet Union and the United States, Bobby Fischer defeated Soviet Boris Spassky to become the first official world chess champion from the United States. Two decades later, after playing a rematch with Spassky in war-torn Yugoslavia, Fischer became a fugitive from U.S. justice. Although always an independent, autonomous, and forthright person, Fischer's behavior after the 1972 championship grew increasingly strange and bizarre. “Who was Bobby Fischer and what happened to him” is a lingering question that has not been adequately answered by psychologists, historians, and biographers. The present article examines the life of Bobby Fischer from three diverse psychobiographical lenses: Erikson's (Erikson, E. H. [1950]. Childhood and society. New York, NY: Norton) psychosocial development model; the clinical diagnostic model of the Shedler-Westen Assessment Procedure (SWAP; Shedler, J. [2009]. Guide to SWAP-200 Interpretation. Shedler-Westen Assessment Procedure: Where Science Meets Practice. www.SWAPassessment.org ); and a strengths-based positive psychology model (Peterson, C., & Seligman, M. E. P. [2004]. Character strengths and virtues: A handbook and classification. Oxford, UK: Oxford University Press.). Suggestions for advancing the science of psychobiography are put forth with particular emphasis on incorporating mixed methods approaches to research.