Ludolf of Żagań, the abbot of the monastery of the Canons Regular (d. 1422), was the author of works that extensively addressed issues of politics. One of the most interesting themes in his writings is the analysis of the starkly contrasting portrayals of the Bohemian kings Charles IV and Wenceslaus IV. The former is depicted by Ludolf as an ideal model of monarchical virtues, while his son is held chiefly responsible for the profound crisis afflicting his domains. Ludolf of Żagań’s reflections offer a compelling example of considerations on secular power, written from the perspective of a monastic chronicler. This paper aims to highlight the differences and similarities in Ludolf’s perception of both rulers and their reigns, as presented in Catalogus abbatum Saganensium and De longevo schismate—works that primarily focus on monastic and ecclesiological themes.