The Islamic Republic of Iran is no doubt an autocratic regime, where the supreme leader, Ayatollah Khamanie, has taken it upon himself to micromanage the suppression of the opposition for many years. In this respect and in the eyes of most Iranians, the resignation and submission of the Iranian reformists, including the former president Mohammad Khatami, is puzzling if not downright treacherous. By appropriating the insight of an Italian Renaissance writer, Baldassare Castiglione, in his book, Il Libro del Cortegiano or The Book of the Courtier, I hope to offer an alternative interpretation of the confounding position of the Iranian reformists. Contrary to its prevalent reading in its scholarship, which takes Il Libro del Cortegiano as an apolitical book, its more recent scholarship has discovered a political program, which in the absence of freedom aims to ameliorate the conduct of the tyrant through the actions of the courtier, who provides an example of honourable conduct and public service. I propose to adopt the ideal of cortegiano as a heuristic device that, when applied to the Iranian situation, can explain Mr. Khatami and his fellow reformists’ acquiescence as a stratagem of resistance that, in the absence of a better alternative, works as the politics of the second best to make their "master" a better leader by offering an example of a more virtuous leader.