Kanetsugu became an Uesugi councilor at the age of 22, quickly distinguished himself as an outstanding commander, he fought at Battle of Tedorigawa and was involved in much of the fighting that took place on the Sea of Japan coast against Sassa Narimasa and Maeda Toshiie.

Ieyasu accused Kagekatsu's castle construction of being a suspected rebellion against the Toyotomi clan and demanded that he come to Osaka to explain.

[4] At that time, Kanetsugu argued that they should pursue the Tokugawa forces, but Kagekatsu prioritized the suppression of the Date and Mogami clans, leading to the rejection of the pursuit strategy.

[5] In order to maintain the pay of Uesugi vassals with such small revenue income, Kanetsugu focused on domestic affairs.

Furthermore, Kanetsugu worked to also obtain information about distribution and market prices from government merchants, and focused on producing local specialties such as safflower and wax.

Meanwhile, he also employ lower-ranking samurai lived outside the castle as part time farmers to further increase the revenue production's input.

[5] As now Kanetsugu facing the reality that the Tokugawa clan now effectiely controlled Japan, he also worked on diplomatic route by taking step to get close to Ieyasu's inner circles.

[5] Following his death, his wife Lady Osen (お船), per the custom at the time, took the tonsure, cutting her hair short and becoming a Buddhist nun.

Dening recount an anecdote in which Hideyoshi, whose temporary unification of Japan paved the way for Ieyasu's shogunate, decides to visit Uesugi Kagekatsu, Kanetsugu's liege lord at the time, in person, accompanied by just a few retainers.

Kanetsugu is also represented, though in fictional female form, in the popular Anime 'Hyakka Ryoran: Samurai Girls', and its sequel 'Samurai Bride'.

In the Light Novel Nekomomogatarai (Black) from the Monogatari Series the protagonist Koyomi Araragi compares himself to Naoe to counter his little sister Tsukihi who accused him of being a "loveless person".