Naoe Kanetsugu, originally called Higuchi Kagetsugu, was originally born in 1560 and became a chief advisor to Kenshin Uesugi and the Uesugi clan. In a somewhat similar manner to Kuroda Yoshitaka, Naoe Kanetsugu’s strong relationship with Hideyoshi Toyotomi began after the Uesugi clan helped Toyotomi fight against one of its rivals: Shibata Katsuie. Following Hideyoshi’s death, Kanetsugu managed to convince the Uesugi clain to join forces with the remainder of Hideyoshi Toyotomi’s vassals against Tokugawa Ieyasu in the climactic Battle of Sekigahara. Naoe Kanetsugu became famous for his hostile letter sent to Tokugawa stating that "while citified samurai busily collect tea implements, country samurai gather arms for war." 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.

Kanetsugu was well known for wearing a helmet affixed with the kanji 愛 (Ai), which means Love

TDuring the year 1601, after the decisive Battle of Sekigahara that resulted in victory for the Eastern army, the Naoe Kanetsugu was transferred to Yonezawa where he eventually became the leader of the Uesugi clan and ultimately died in 1620. Kanetsugu was well known for wearing a helmet affixed with the kanji 愛 (Ai), which means Love. Though Kanetsugu is not as famous as many other samurai from this time, he still played an important role in the Sekigahara campaign. As such, anyone can find the statue of him in front of the Yoita History and Folk Museum in Niigata Prefecture of Japan, along with ample references throughout anime and games (e.g. Sengoku Basara).