This study examines Leo Strauss’s reading of ancient philosophers on the relationship between the politician and philosophical life. We seek to answer these two questions: What does Strauss’s invitation to us to connect with the ancient form of the project of philosophy and politics, or at least to place this ancient form as a starting point for their wise application in today’s society, first tell us about the relationship between philosopher and politics? What does it tell us about the relationship between philosopher and politics? In response to the crisis of modern political philosophy, Strauss invites us to observe the behavior of philosophy and politics among the ancients from Plato to Xenophon. What he himself calls classical political philosophy. The goal is to reach an understanding of Leo Strauss’s understanding of these two ways of life. At the heart of this rationalism lies the classicists and their way of looking at philosophy, the city, politics, and the politician. In this recovery of the ancients' sense of politics, Strauss mentions the nobility of the politician/gentleman as someone who stands before the philosopher at the dawn of the city. He believes that the gentleman has a more natural view of the nature of the city and politics than anyone else, so the philosopher approaches the city through moderation and wisdom from the perspective of a gentleman rather than a partisan.