Stories of the Japanese 01244 [Muromachi/Yoshimitsu Period] Shiba Yoshimasa, Kanrei for the Third Time

April 26, 1393 (Meitoku 4). Retired Emperor Go-Enyu passed away. Although he struggled with his relationship with Yoshimitsu, he had narrowly won the imperial succession dispute against his cousin (Prince Eihito) and was able to pass the throne to his son (Emperor Go-Komatsu), so he must have been satisfied.
Then, in June 1393 (Meitoku 4), Hosokawa Yorimoto resigned as Kanrei, and Shiba Yoshimasa returned to the post as his successor. Presumably, with the death of Yoriyuki, his adopted son Yorimoto had lost his backing.
Looking at the successive Kanrei to date, they are as follows:
1st: Shiba Yoshimasa (in office 1362–1366)
The second Shogun, Yoshiakira, made Yoshimasa, the son of Shiba Takatsune, the Kanrei in order to win back Takatsune, who had defected to the Southern Court, to the side of the Shogunate—in other words, to appease him. Yoshimasa was 12 years old at the time of his appointment, and surely no one thought at that point that he would become a talent capable of carrying the Shogunate on his shoulders. Four years later, when his father Takatsune betrayed the Shogunate again, his son Yoshimasa also fell from power.
2nd: Hosokawa Yoriyuki (in office 1367–1379)
He was the person Yoshimitsu trusted most; he strengthened control over powerful Shugo and laid the groundwork for ending the Northern and Southern Courts period, but he fell from power due to the Koryaku Political Incident caused by the Shiba faction.
3rd: Shiba Yoshimasa (in office 1379–1391)
This was his second term. Having left his father Takatsune's influence and standing on his own, Shiba Yoshimasa plotted in various ways to oust the Hosokawa faction, but it did not go well. Yoshimitsu called Yoriyuki back to Kyoto, causing Yoshimasa to fall from power once again.
4th: Hosokawa Yorimoto (in office 1391–1393)
Although Yoshimitsu called Yoriyuki back, Yoriyuki himself had already become a monk, so he installed his adopted son (younger brother) as Kanrei. However, he did not display the same individuality as Yoriyuki, and with Yoriyuki's death, he lost his backing and fell from power.
5th: Shiba Yoshimasa (in office 1393–1398)
Yoshimasa was appointed Kanrei for the third time.
As you can see by looking at the successive Kanrei, the internal conflict between the Hosokawa faction and the Shiba faction continued throughout. Yoshimitsu was, of course, on the side of the Hosokawa faction, but in the end, he never managed to destroy the Shiba faction. Perhaps upon his third appointment as Kanrei, Shiba Yoshimasa gave up on overthrowing the Hosokawa faction and began to seek a path of coexistence. Yoshimitsu and Shiba Yoshimasa maintained a certain level of tension, but they never parted ways.