The 1950s gave an important impulse to the birth of Medieval and Humanistic Philology and in general to Neo-Latin studies: however, there are still few contributions dedicated to the intellectuals of that period, and investigations about their approach and objectives. The aim of this paper is to propose a critical reflection on the first monograph dedicated to Tristano Caracciolo by Mario Santoro in 1957, and on the method with which the scholar approached the reading of the works of the Neapolitan humanist. After analyzing the way in which Caracciolo’s works are cited and the quality of the quotations, particular attention has been paid to the historical and cultural context in which Santoro’s interests in humanistic literature were born, a period that we can define of great change and crisis of traditional values. The pedagogical meaning of Caracciolo’s thought is emphasized to the point that Santoro builds a singular parallelism between the Neapolitan culture of the early Sixteenth Century and that of the 1950s.