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This chapter introduces classical ideas of leadership, from Homer's Iliad and Odyssey and Xenophon's Anabasis, posing questions that challenge the ethical and value-based stance of the contemporary literature on authentic leadership. Do leaders in all spheres need to be versatile in the classical sense? Is the use of ruses legitimate if they succeed? Do literature and history provide greater insight into the execution of leadership than conventional business school courses? Pieper urges researchers to investigate the qualities that a leader needs and the values espoused by proponents of authentic leadership and what coherent theory that recognises the leadership imperatives exemplified by the heroic classical accounts could replace the model of authentic leadership.