In the bakufu (Japanese feudal government headed by a shogun), he assumed the position of oshobanshu (senior representative) and acquired the trust of Yoshimasa ASHIKAGA, who was shogun and, during Kansho era, it was a customary that Yoshimasa visit Yoshinao's kyoyakata (mansion in Kyoto) ("Inryoken Nichiroku," a diary of the owner of Inryoken).
幕府においては、御相伴衆となり将軍足利義政の信頼を得、寛正年間は毎年2月17日に義直の京屋形に義政が訪れるのが慣例となっていた（『蔭凉軒日録』）。