The article examines the miniatures of the Radzyvill Chronicle. It attempts to discriminate between real and fictional emotions of a person from the Middle Ages and focuses on the expressions of sorrow and crying. In historical studies of emotions, images are crucial. They record both real manifestations of emotions and ideas about their importance, expediency, essence. The article relies upon iconographic method, as well as upon semiotics, historical-comparative and content analysis. We assume that sad emotions have more expressiveness in the visual manifestations. Reading facial expressions in miniatures or painting can be challenging. Thus, we rely on interpreting a hand near the cheek or the hem of a garment pressed to the face or sleeves that are down as a universally recognized gesture of sadness. This paper offers a first insight into the miniatures of the Radzivil Chronicle, which depict sadness and crying. It examines emotions through narrative and visual strategies of the Chronicle and reveals how it fits within the tradition of showing tears and sadness in medieval society. After studying the Chronicle, we can conclude that it did not deal with emotions extensively. Only 25 of the 613 miniatures of the Königsberg list (which is 4% of all images) convey unhappy emotions. The miniatures from the Radzyvill chronicle confirm the three main states where sadness and weeping corresponded with the decorum of medieval Rus: the death of loved ones, common misfortunes or public troubles like captivity and separation-farewell. Therefore, the emotions depicted in the Chronicle were historically conditioned. Sadness was conveyed in illuminations that dealt with the departure from this world and burials of princes and clerics, the military conflicts, which affected people’s lives. Sometimes the emotions were not mentioned in the accompanying text, but only conveyed through the visual means, which reveals medieval behavioral models and ideas about crying as a natural emotional reaction to the death and burial of the loved ones and to the misfortunes associated with captivity. The absence of illustrations of sadness and tears in the Pechersk cycle of miniatures is generally consistent with the tradition of illustrating texts where attention was paid to actions and not to emotions. This fact, too, may indicate the understanding of tears of repentance and prayer as an internal state that is not conveyed through external means.