Sheftall graduated from Stuyvesant High School in New York City, attended the United States Military Academy at West Point for two years as a member of the Class of 1984, and received a B.A. in Political Science/International Relations from Fordham University in 1985.
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He holds Master's degrees from California State University and the University of Birmingham, and received his Ph.D in International Relations Studies from Waseda University in Tokyo.
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He is a professor of modern Japanese cultural history and communication in the Faculty of Informatics at Shizuoka University, a branch campus of the Japanese national university system.