Talking about “Trumpism” is probably the wrong approach to Trump, but there are other pitfalls when speaking about the 45th president’s impact on political life. Notably, partisan strife is held to an overly strict standard: it is as if the president could not be harming American politics unless there were pitched battles in the streets. Xenophon’s portraits of men who want or exercise power proves to be a middle ground between trying to examine any “Trumpist” ideology or the immediate political ramifications of Trump’s actions. I compare Trump to Glaucon in Memorabilia III.1–7, Meno from the Anabasis, and Hiero from the work of the same name. What I find is a man Xenophon would struggle to comment on—the president is not the sort of man who would easily qualify for the ranks of the unworthy. His shamelessness, greed, and lust for power reflect broader, complicated political vices we share.