Ivan III of Russia
In 1470, Johann Wolthus von Herse, then master of the order, took up residence in the castle. In the Middle Ages, Viljandi was a typical small commercial town, which got its main income from transit trade. The local trade and handicraft played an equally important role. In 1481, Ivan III of Russia laid siege to the castle but could not take it. The decline of Viljandi started during the Livonian War and in 1560, the forces of Knyaz Andrey Kurbsky of Muscovite Russia succeeded in seizing and demolished the town and the stronghold.