Xenophon’s interest in the role of elite Athenians in the democratic city is evident not only in his manifestly Athenian works where this is an explicit concern but also elsewhere in his corpus, most notably in his Anabasis, the focus of this chapter. Although this work tells the story of how a band of Greek mercenaries marched with Cyrus into the heart of the Persian Empire in 401 BC, Xenophon’s account is profoundly affected by his Athenian experience and interest in elite political behavior within the Athenian democracy. The Anabasis broadly evokes the political situation in Athens and the complex interactions of mass and elite as Xenophon depicts the importance of and challenges for elite leadership in the quasi-democratic setting of the Cyrean army. In setting forth how a versatile elite Athenian – Xenophon himself – succeeds as a leader of the Cyreans, it confirms in action the principles that Xenophon lays down elsewhere for effective elite leadership within the Athenian democracy. It portrays Xenophon not just as a talented general but as a capable democratic orator who wins over the Cyrean masses in deliberative and forensic contexts that recall their Athenian analogs.