Following the death of Nobunaga ODA, Harusue, enjoying a close friendship with Hideyoshi TOYOTOMI, in power at that time, attempted to attain the position of seii taishogun (literally, "great general who subdues the barbarians") through positioning himself as the adopted son of Yoshiaki ASHIKAGA, yet was rejected by Yoshiaki, and when at the point of abandoning the shogunate it was suggested he become the kanpaku (Chief Advisor to the Emperor) and subsequently he worked in the Imperial Court in mediation and arbitration.
晴季は豊臣秀吉と親密な間柄で、織田信長亡き後、秀吉が天下人として、征夷大将軍の位を得ようとし、足利義昭の猶子となろうと工作したものの、義昭の拒否に遭い、将軍職を諦めていた所に関白任官を持ちかけ、朝廷における斡旋、調停役を務めた。