 During the Novgorod campaigns of 1492 and 1495, he was one of the commanders of the so-called Big Regiment (Большой полк) and was noted by Ivan III for his bravery in combat.Ivan would soon admit him to his circle of friends and royal court.In 1500, the grand prince arranged a marriage between Vasily Kholmsky (who was a descendant of appanage princes of Tver) and his second daughter Feodosiya Ivanovna (died February 19, 1501) and bestowed the title of a boyar upon Vasily.