This article evaluates once more the historiographic and literary images of John of Bohemia and his son Charles IV in Italian texts from the 14th and early 15th centuries. What we find is a peculiar mixture of criticism and apotheosis, sometimes stated by the same authors, depending on the point in time they were writing, and of course the expectations of their potential readers. While John of Bohemia faced overwhelming expectations from Dante after the death of his father, he was branded a naïve yet greedy papal mercenary from the beginning of his Italian Expedition in the early 1330s. His son was more successful in avoiding negative stereotypes and harsh criticisms during his Italian expeditions in his youth, as well as in 1354/55 and 1368/69. In the end, however, even chroniclers that are traditionally considered to have had a positive view of the Luxemburg king and emperor harshly rejected his political actions in Italy. Most of the time, this is connected with the financial interests all foreign monarchs had when establishing temporary rulerships in Italian cities, and the monetary pressures this bore on their citizens; the worn-out cliché, both of contemporaries and historical researchers, that labelled foreign, Central European monarchs as barbaric intruders, could hardly be confirmed. Charles and his father are blamed for being unable to solve the structural problems of Italian and Imperial politics.