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Updated: June 13, 2025
This being an enterprise of large dimensions, he entrusted its conduct to five of his most competent generals, namely, Ukita Hideiye, Hachisuka Iemasa, Kuroda Nagamasa, Kikkawa Motoharu, and Kohayakawa Takakage.
This part of the enterprise was entrusted solely to Asano Nagamasa, minister of Justice, one of the five bugyo, that is to say, five officials called administrators, in whose intelligence and competence Hideyoshi placed signal reliance.
Meanwhile and this step also was undertaken under Hideyoshi's advice a friendly contract had been concluded with Asai Nagamasa, the most powerful baron in Omi, and the agreement had been cemented by the marriage of Nobunaga's sister to Nagamasa. In October, 1568, Nobunaga set out for Kyoto at the head of an army said to have numbered thirty thousand.
Such was the case with the son of Hosokawa Tadaoki; with Goto Matabei, chief vassal of Kuroda Nagamasa, and with Nambu Saemon, principal retainer of Nambu Nobunao. These three and many others repaired to the castle of Osaka, and being there secure against any unarmed attempt of the Tokugawa to arrest them, they virtually defied Ieyasu's control.
This lady was a sister of Nobunaga. She had been given, as already stated, to Asai Nagamasa, and to him she bore three children. But after Nagamasa's destruction she was married to Katsuiye, and was living at the latter's castle of Kitano-sho when the above incidents occurred.
He himself would have directed his forces at once against Nagamasa, but Hideyoshi contended that the wiser plan would be to endeavour to win over some of the minor barons whose strongholds lay on the confines of Omi and Mino. The former was attacked first, Nobunaga being assisted by a contingent of five thousand men under the command of Ieyasu.
Success crowned the early efforts of the Owari forces in this war, but the whole situation was changed by Asai Nagamasa, who suddenly marched out of Omi and threatened to attack Nobunaga's rear. It is true that before setting out for Kyoto originally, Nobunaga had given his sister in marriage to Nagamasa, and had thus invited the latter's friendship.
Three days of repeated assaults failed to reduce the castle, and during that interval Nagamasa and Yoshikage were able to enter the field at the head of a force which greatly outnumbered the Owari army. In midsummer, 1570, there was fought, on the banks of the Ane-gawa, one of the great battles of Japanese history. It resulted in the complete discomfiture of the Echizen chieftains.
But Nobunaga was saved by the slowness of Nagamasa, who, had he moved with any rapidity, must have reached Kyoto in advance of Nobunaga's forces; and Hideyoshi was saved by an exercise of the wonderful resourcefulness which peril always awoke in this great man.
This result was intensely mortifying to Hideyoshi, who had devoted his whole energies to the destruction of these dangerous enemies. But the final issue was only postponed. By contrivances, which need not be related in detail, Nagamasa was again induced to take the field, and, in 1573, the Owari forces found themselves once more confronted by the allied armies of Echizen and Omi.
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