The figures of the great conquerors of the Orient were extremely attractive during the Renaissance. Therefore, a whole series of treatises dedicated to Tamerlane and Bayezid appeared. Due to cultural and linguistic differences, the writings of European authors created and developed the legendary narrations of questionable content about the leaders of the Orient. Such discrepancies gave space for creativity to authors in that epoch. One of such legends narrates about the grievous enthralment of the Turkish Sultan Bayezid, who fell into Tamerlan’s arms after the defeat at Ankara (1402). Thanks to the writings of Piccolomini (Pope Pius II), Buonaccorsi-Kallimachus, Bracciolini, the assertion that the sultan was put in a cage, he was in shackles (sometimes golden) and served as a stand for Tamerlane when he sat on a horse, spread. Historical narratives influenced literary and visual works. The article examines the origin of such a legend. I presume that the legend of imprisonment of Bayezid rooted in the work of Dietrich of Nieheim, who compiled his work “Three Books on Schism” at the beginning of the 15th century. This book has a separate part about Tamerlane. This chapter also mentions a prayer to St. Leonard, who was the patron saint of prisoners. It was customary to depict St. Leonard with handcuffs and chains. His relics, after their discovery in 1403, were placed in a cage on the altar. Churches dedicated to the saint were decorated with images of chains. On the ground of St. Leonard’s cult the legend about the supposed imprisonment of Bayezid in a cage was created. Such a legend circulated not only in the texts of the historiographical or cosmographical nature. It also inspired authors of literary works and artists. The legend about imprisonment of Bayezid in the cage has been included into Polish and Ukrainian historical narrations. Thanks to Bernard Wapowski’s Chronicle, the legend about Bayezid’s grievous enthralment was added to the story about the military campaigns of the Lithuanian prince Vytautas against the Hordes. The first of these campaigns took place probably in the mid-1390s, while the second battle of the Vorskla river, which is clearly dated, occurred in 1399. This second expedition, which ended in the defeat of the Lithuanian troops, is recorded in Polish, Lithuanian, and Ukrainian historiography during the Renaissance. It seems that Wapowski followed the narration of Maciej Miechowita, who first mentioned about Tamerlane in the context of the defeat of the Lithuanians. The spread of the legend in Ukrainian historical writings of the 17th century is good evidence that the local elite was eager to learn about the past. The research methodology of this article is based on the comparative study of sources of historiographical and cosmographical content. Sources written in Italian, French, English, Latin, German, Greek, Polish and Ukrainian have been involved for this research. The legend’s inclusion in the texts of the chronological and cosmographic characters sheds light on the processes involved in the Renaissance construction of historiography. The fact that these publications allowed the curious European public to learn about the people and customs of the Orient is equally significant.