Vasily Kholmsky, a nobleman from Moscow, served as one of the commanders of the Big Regiment (Большой полк) during the Novgorod campaigns of 1492 and 1495.
Recognizing Kholmsky's bravery in battle, Ivan III admitted him to the royal court and welcomed him to his circle of friends.
In 1502, Vasily Kholmsky and Dmitry Ivanovich, son of Ivan III, fought against the Lithuanians in the Smolensk region.
[citation needed] In 1505-1506 Kholmsky resumed command of the Big Regiment and was ordered to defend Murom and Nizhny Novgorod.
Upon hearing the news, Kholmsky's troops, stationed in Mozhaisk at the time, immediately mobilized and defeated the Lithuanian army at Vyazma.