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He had succeeded to that office in 1367, at the age of nine, and his father, then within a year of death, had entrusted him to the care of Hosokawa Yoriyuki, one of the ablest men of his own or any generation. There are strong reasons for thinking that between this statesman and Masanori an understanding existed.

In 1391 Yamana Ujikiyo and his kinsman Mitsuyuki took the field against Kyoto under the standard of the Southern Court. He commanded a great army, and there resulted a desperate struggle known in history as the Meitoku War, after the name of the year-period when it occurred. The Yamana leader was killed and his army completely routed. In the following year, the great Hosokawa Yoriyuki died.

There is little question that whatever applause history can extend to the administration of the third Ashikaga shogun, Yoshimitsu, was won for him by his profoundly sagacious guardian and chief minister, Hosokawa Yoriyuki. After the latter's death, in 1392, many abuses and few meritorious acts appear in the shogun's record.

The most prominent figures in the closing chapter of the great dynastic struggle are Hosokawa Yoriyuki and Yamana Mitsuyuki. When the second Ashikaga shogun, Yoshiakira, recognized that his days were numbered, he summoned his trusted councillor, Hosokawa Yoriyuki, and his son Yoshimitsu, and said to the latter, "I give you a father," and to the former, "I give you a son."

Yoriyuki faithfully discharged the trust thus reposed in him. He surrounded his youthful charge with literary and military experts, and secured to him every advantage that education could confer.

During ten years he remained in seclusion. But, in 1389, a journey made by the shogun to Miya-jima revealed so many evidences of Yoriyuki's loyalty that he was invited to return to Kyoto, and with his assistance the organization of the Ashikaga forces at Muromachi was brought to a high state of efficiency, partly because the astute Yoriyuki foresaw trouble with the Yamana family, which was then supreme in no less than ten provinces, or nearly one-sixth of all Japan.

Ryoshun had been selected for service in Kyushu by the great shitsuji of Muromachi, Hosokawa Yoriyuki, who saw that only by the strongest hands could the turbulent families of the southern island be reduced to order the Shimazu, the Otomo, the Shoni, and the Kikuchi. Everything went to show that Imagawa would have succeeded had not that familiar weapon, slander, been utilized for his overthrow.

Hosokawa Kiyouji, returning to his native province, Awa, essayed to bring the whole of Shikoku into allegiance to the Southern Court, but was signally worsted by his cousin, Hosokawa Yoriyuki afterwards very famous, and scarcely a month had elapsed before Yoshiakira was back in the capital.

This daimyo was a puissant rival of the Ouchi family, and on the downfall of the latter he soon came into collision with Mori Motonari. Early in the fourteenth century, the celebrated Hosokawa Yoriyuki was banished to Sanuki, and in the middle of the fifteenth century we find nearly the whole of the island under the sway of Hosokawa Katsumoto.