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This paper describes a course entitled “Leadership and the Ancient World” and details some of the challenges and trends in higher education which make a course focused on the Classics and leadership desirable. The paper summarizes conventional approaches to leadership and emphasizes the advantages of a liberal-arts based approach starting with the Classics. We explain our basic course design; offer a summary of how the course was run; and present sample activities. In closing, we present assessment and evaluation data for the course and remark on ways in which the syllabus and design could be improved in future iterations.