Hisatake Chikanao served as a bushō during the Azuchi-Momoyama period. He was a retainer of the Chōsokabe clan of Tosa Province. His common name was Kuranosuke and childhood name was Hikoshichi.
Chikanao was born as the second son of Hisatake Masamoto and his older brother was Hisatake Chikanobu. Perhaps owing to concerns in regard to Chikanao’s character, Chikanobu informed his lord, Chōsokabe Motochika, that if he (Chikanobu) were to be killed in battle, not to allow Chikanao to become the successor because it would be harmful to the family.
In 1579, however, after Chikanobu was killed, Chikanao did inherit the family. In the autumn of 1584, Chikanao was appointed as the gundai, or representative in battle for his lord, in Iyo Province. On 9/11 of Tenshō 12 (1584), he attacked Fukada Castle in Iyo.
In 1587, at the Battle of Hetsugigawa, the death in battle of Motochika’s eldest son, Chōsokabe Nobuchika, triggered a succession struggle. Chikanao supported Motochika’s fourth son, Chōsokabe Morichika, while other retainers named Kira Chikazane and Hieyama Chikaoki supported Motochika’s second son, Kagawa Chikakazu. Either owing to slander by Chikanao or as a result of repeated appeals by Chikazane, Motochika became angry and ordered Chikazane and Chikaoki to commit seppuku.
After the defeat of the Western Army at the Battle of Sekigahara in the ninth month of 1600, Chikanao overcame arguments to go to war and advised Morichika to submit to Tokugawa Ieyasu. However, at the same time, he recommended killing Morichika’s older brother, Tsuno Chikatada so Morichika was removed from his position by Ieyasu for having killed his older brother. In this way, after successive purges of feuding parties within the Chōsokabe family, Chikanao was regarded by some as an uncommonly treacherous retainer who acted as the main culprit in the eventual elimination of the Chōsokabe family.
Later, he served Katō Kiyomasa of the Higo-Kumamoto domain in Kyūshū.