Akai Naoyoshi served as a bushō in the Azuchi-Momoyama period and a hatamoto in the Edo period. Naoyoshi was the son of Akai Naomasa, known as the Red Demon of Tanba Province.
Naoyoshi was nine years old when Naomasa died of injuries sustained in battle. His uncle, Akai Yukiie, served as his guardian. However, following multiple attacks by Akechi Mitsuhide, Yukiie lost Kuroi Castle and fled. He then led a secluded life in Kyōto, changing his name to Ogino Kinsaemon. In 1610, through the introduction of Yamaguchi Naotomo, Naoyoshi served Tōdō Takatora and awarded a fief of 1,000 koku. He then reverted to his previous surname. In 1615, Naoyoshi served on behalf of Takatora as a commander of ashigaru, or foot soldiers, at the Siege of Ōsaka.