This chapter explores Plutarch’s presentation of greatness as it equates with leadership ability and outcomes. He expressly values civic participation and leadership that aims to secure and promote the welfare of the community. Subsequent to the presentation of some basic information concerning his theories of education, especially ethical education, attention is then focused on the innate components of greatness and the appropriate means to develop this inborn talent in training individuals to wield power in an effective and responsible fashion. A comparative analysis is then undertaken to set forth the similarities and differences between the psychological/behavioral makeup of Plutarch’s ideal leader and recent influential work in leadership theory by Daniel Goleman, James MacGregor Burns, and Bernard M. Bass. The significant degree of correspondence elucidated leads to a discussion of the literary techniques Plutarch employs to place in sharper relief the salient aspects of great leadership (and its opposite), including his developed use of synkrisis and the Socratic paradigm, as well as the representation of performative acts of leadership.