Naoe

Naoe Kanetsugu was born in 1560. Because of his intelligence, he quickly became a chief advisor to the Uesugi. In the civil war that was fought between Uesugi vassals following Kenshin's death, he supported Uesugi Kagekatsu. In 1579, Kagekatsu emerged as the victor. Because he had supported Kagekatsu in this war, when the lord of Yoita Castle, Naoe Nobutsuna, died, Kagekatsu ordered Nobutsuna's widow to marry Kanetsugu. Thus Kanetsugu (who at the time was still named Higuchi Kagetsugu) became Naoe Kanetsugu and the inheritor of Naoe Nobutsuna's domain (which he would keep until the Uesugi clan was transferred to Yonezawa by Tokugawa Ieyasu). During and after the Uesugi conflict, the Oda Clan converged upon Uesugi Kagekatsu's territories and nearly wiped the Uesugi off the map. However, when Oda Nobunaga died, Uesugi Kagekatsu won favor with Hideyoshi by attacking Shibata Katsuie. This was during a time when Shibata Katsuie and Toyotomi Hideyoshi were at odds with one another, and so the Toyotomi and Uesugi became strong allies thereafter.

Following Hideyoshi's death, Uesugi Kagekatsu decided to build up his army. Tokugawa Ieyasu, who feared that the Uesugi might go to war with him, demanded that Kagekatsu stop this. Supporting Kagekatsu's plan to strengthen the Uesugi army though, Naoe Kanetsugu wrote a hostile letter to the Tokugawa stating that "while citified samurai busily collect tea implements, country samurai gather arms for war." Soon after, the Uesugi arranged an alliance with Ishida Mitsunari, one of Toyotomi Hideyoshi's former administrators, against the Tokugawa.

In the events that led up to the Battle of Sekigahara, Naoe Kanetsugu moved swiftly in an attempt to jeopardize Tokugawa Ieyasu's holdings in Japan's Kanto Province. After a brisk siege, he managed to take Hataya Castle. However, two daimyo of the North, Date Masamune and Mogami Yoshiaki, successfully countered Naoe Kanetsugu and defeated him in the Battle of Hasedou. During the year 1601, after the decisive Battle of Sekigahara that resulted in victory for the Eastern army, the Uesugi clan was transferred to Yonezawa. Naoe Kanetsugu received a fief there. Soon after, Kanetsugu retired, though before the end of his life he would write a law code called "Orders for Peasants" Naoe Katsushige (who was adopted) and Naoe Kageaki succeeded Kanetsugu after the latter's death in 1619.

Though Kanetsugu is not as famous as many other samurai from this time, he still played an important role in supporting Ishida Mitsunari during the Sekigahara campaign.