This chapter argues that notwithstanding the Symposium’s debt to its more famous Platonic predecessor, Xenophon exploits the symposiastic setting to serve his own purposes and interests, as Socrates, assisted by Antisthenes, seeks to educate Callias, a super-rich Athenian, concerning proper elite values and behavior in the democracy. Callias’ naive assumptions concerning his wealth and its capacities are challenged and laid bare, and ultimately Socrates instructs him on how he can live up to the high expectations of a man of wealth and high birth by seeking political knowledge, pursuing leadership positions within the city, and fostering the same ambitions in the boy Autolycus, whom he loves, within the context of a mutually supportive friendship (philia). As such, the Symposium constitutes a case study in the education of a conspicuous member of the Athenian elite concerning the political role to which he should aspire within the city. Although Xenophon portrays Callias as a challenging student to educate, he shows his Socrates doing his best to recruit a prominent elite Athenian to serve the democratic city.