Hirotada was always a supporter of Takenaka Okawa and after the Hojo War he was nominated shugo-daimyo of Miyama by the shikken. In 1357 DR, he was in a difficult situation because he was personally loyal to Okawa but his wife was daughter of Takenaka Sugawara and Hirotada tried to remain neutral in the brothers' conflict. He was developing a strong power base in the province.
Hirotada was a straightforward and honest individual, known to seldom reveal any unnecessary details in conversation. He was also very cunning and intelligent. Above all, he was truly patient, always waiting for the right time to do things. He believed that the conflict between court and bakufu would end with a disaster and that that day he would be ready to be the absolute ruler of Miyama.