The article presents a historical-philosophical study of the book The City and Man published in 1964 by the political philosopher Leo Strauss. Using a large amount of material, the author attempts to assess the place the book holds in Strauss’ legacy. Additionally, the author presents his own interpretation. Highlighting that The City and Man is mostly concerned as a marginal work in comparison to other of Strauss’ papers, he gives and analyzes a number of political interpretations of the book. Not being content with any of them, he presupposes that The City and Man should be considered in the context of classical political philosophy research undertaken by Leo Strauss. Analyzing each of the three chapters of the book dedicated to Aristotle’s’ Politics, Plato’s Republic and Thucydides’ History of the Peloponnesian War, the author concludes that all three texts are interconnected through the figure of one man. This man is Socrates, who discovered sanity and reason as the basis of political philosophy. Each of these works has sanity and reason at their roots, which is a foundation for the revival of political philosophy. By comparing virtue and city (polis) as terms of classical political rationalism, we could shed light on the actual problem of the relationship between ethics and law.