Investigating the propaganda surrounding the grand duke, this study reveals that, in fact, there were two opposite images: that of a good ruler and that of a tyrant. The paradox is that frequently these opposites were based on the same features of the grand duke's character or episodes from his biography. The research is based on a wide array of written and visual sources as well as on records of oral tradition. Rich and diverse primary materials are analysed from the perspectives of political and social history, memorial culture, as well as iconography and rhetoric.