By the mid-sixteenth century, the Vorotynsky princes were highly sought aft er for their military service within the Russian state. Th e brothers of the Vorotynsky family served as regimental commanders, at times leading substantial independent fi eld formations, in addition to garrisons of major cities and fortresses. In the autumn of 1562, however, the Vorotynsky family fell into disgrace. Th is decline was particularly marked in the case of Prince M.I. Vorotynsky and his brother A.I. Vorotynsky, whose lands were confi scated (Prince V.I. Vorotynsky had already died). Th e severity of the disgrace is also refl ected in its duration; for the elder brother, it ended only in 1565. Mikhail Ivanovich and his wife were imprisoned in Beloozero, while Aleksandr Ivanovich and his wife were detained in Galich. As a result, the Vorotynskys, who were major generals, were permanently expelled from the Russian voivodeship corps. Th e reasons for the disgrace of the Vorotynskys have been a subject of speculation among experts. One commonly held view is that it was a consequence of Ivan IV’s desire to destroy the vast Vorotynsky Principality, refl ecting the course of the Tsar’s land policy. Conversely, alternative theories have postulated that the Vorotynskys’ decline can be attributed to the prevailing political dynamics of the era. Th e present author puts forward an alternative hypothesis, namely that the Vorotynskys were punished for their failure to defeat the Crimean Khan Devlet-Giray near Mtsensk in the summer of 1562. Th e Khan managed to evade capture and retreat onto the steppes, thereby circumventing a potential defeat at the hands of the Russian voivodes. Th is outcome is attributed to the Prince M.I. Vorotynsky’s slowness in command, specifi cally with regard to the Russian troops’ defensive formation. Th is event is likely to have resulted in the monarch’s censure of the prince’s performance in a senior position. During deliberations among experts specializing in the military and political history of the Russian Empire, analogous assumptions have been posited on at least two occasions. A.A. Zimin and V.P. Ul’yanov have expressed views that are similar to these. Th e present author’s position differs from that of his predecessors in terms of its validity, which is derived from a meticulous examination of the sources, specifi cally razriad (register) records and chronicles.