In the 16th century, the monastery was the second richest landowner in Russia, after its model, the Trinity Monastery near Moscow. Ivan the Terrible not only had his own cell in the cloister, but also planned to take monastic vows here. The cloister was also important as a political prison. Among the Muscovite politicians exiled to Kirillov were Vassian Patrikeyev, Tsar Simeon Bekbulatovich, Patriarch Nikon, and the prime minister Boris Morozov. In December 1612, the monastery was besieged by Polish-Lithuanian vagabonds, the Lisowczycy, who failed to capture it.