Naoe Kanetsugu had displayed great prowess from an early age. Uesugi Kagekatsu’s mother, Sentōin, recognized his potential and subsequently selected him to become the page for the young Kagekatsu when he was six years old in 1566.

Kanetsugu also travelled with Kagekatsu, who had been made the adopted son of Uesugi Kenshin, to Kasugaya Castle to learn the arts of battle from Kenshin himself.

After being defeated at the battle of Sekigahara, Kanetsugu was moved with Kagekatsu to Yonezawa. There, he initially worked to build up the town with the aim of housing Kagekatsu’s men.

New construction at Yonezawa Castle, the maintenance of the samurai and merchant housing districts, and improvements to the irrigation system are just a handful of examples of what Kanetsugu managed to achieve shortly after arriving in Yonezawa. He also implemented flood prevention systems, backed local industries, and created education incentives during his time in administrative power.