The aim of this paper is to elucidate a particular vision of the concept of tyranny as presented in the works of Antonio de Guevara (c.1480-1545), one of the most distinguished and influential Spanish scholars in the Sixteenth Century. Guevara contributed to the shaping of many meaningful terms and ideas that kindled the cultural ambiance of his days. Furthermore, this Spaniard’s writings establish a dialogue with the works by the leading figures of the European Renaissance, such as More’s Utopia, Erasmus’ Institutio principis christiani or The Courtier by Castiglione. The detailed analysis of Guevara’s texts will show how the Renaissance revitalized Classical motifs instilling into them new meanings. This is the case, for example, in the case of genres such as the Specula (Principis or Militis). Guevara claims for a proper education for both the prince and the court, concluding that sovereignty must be properly supported by the ethical (or even intellectual) principles of the monarch.