During the Muromachi Period they passed on the stewardship of the Kamakura Kubo and subsequently the Kanto Kanrei position (a shogunal deputy for the Kanto region) through hereditary succession, and they also prospered as a powerful shugo daimyo family that held the governorship of Sagami, Musashi, Kozuke and Echigo Provinces.
室町時代は鎌倉府にあって鎌倉公方の執事、次いで関東管領の職を世襲し、相模国、武蔵国、上野国、越後国など一門で4ヶ国の守護職を占める有力守護大名としても栄えた。