Known as the cruelest 'Assassination Daimyo,' he primarily utilized poisoning and matchlock firearms for his hits. Born in 1529 as the son of Ukita Okiie. In 1534, his grandfather Yoshiie was assassinated by Shimamura Morizane and others, forcing Naoie to flee with his father. Upon reaching adulthood, he served the regional daimyo Uragami Munekage. At the time, the Uragami clan was divided between Munekage and his brother Masamune, and the Ukita clan was similarly split between Naoie and Kunisada, who served Masamune. Naoie defeated and killed Kunisada, seizing leadership of the Ukita clan. Possessing brilliant strategic intellect, Naoie steadily expanded his own territory even while working to enlarge the Uragami clan's influence. To avenge his grandfather, he began by assassinating Shimamura Morizane. He frequently employed schemes such as marrying the daughter of Nakayama Nobumasa to become his son-in-law, only to assassinate him once his guard was down, or killing Munesho Mototsune, the lord of Tatsunokuchi Castle. He often married off his own daughters to targets to establish kinship, then struck when they least suspected him, showing no hesitation in sacrificing his own family members in the process. In February 1566, he hired a ronin from the Hosokawa clan to assassinate Mimura Iechika of Bitchu, who was attempting to advance into Mimasaka Province north of the Uragami lands. The following July, at the Battle of Myozenji, he successfully drove out the Bitchu forces that had advanced into western Bizen Province. Subsequently, he brought about the downfall of the father-son duo Matsuda Mototeru and Motokata of Kanagawa Castle—to whom he was related by marriage—as well as Kanamitsu Munetaka of Okayama Castle, seizing their lands as his own and becoming the most powerful figure within the Uragami clan. In 1569, he finally conspired with Oda Nobunaga and Akamatsu Masahide to rebel against his lord, Uragami Munekage. However, following Akamatsu's defeat and Oda's withdrawal, he was forced to surrender to Munekage and beg for forgiveness. Later, he allied with the Mori clan and rebelled again in 1574, installing Munekage's young grand-nephew (Masamune's grandson), Hisamatsumaru, as a figurehead. By sowing discord between the Uragami generals and their lord, he successfully neutralized Munekage's power and finally took control of Bizen Province. He continued to expand his influence into Bitchu and parts of Mimasaka, attacking the Miura clan of Bitchu. Once Hisamatsumaru was no longer useful, Naoie had him poisoned. He then focused his efforts on suppressing the remnants of the Uragami clan. In December 1578, he faced a crisis when Uragami remnants within Bizen and clan members who had fled to Harima launched a simultaneous uprising, capturing the Kojima region. However, he eventually suppressed them and completely uprooted the Uragami clan. When Hashiba Hideyoshi, acting on Oda Nobunaga's orders, began his advance, Naoie eventually submitted to Nobunaga after a period of resistance. Thereafter, he fought in various locations, repeatedly engaging in battle against the Mori clan. He died at Okayama Castle in December 1581. He was the older brother of Ukita Tadaie and the biological father of Ukita Hideie. Ukita Naoie possessed a meticulous personality, often feigning foolishness to hide his superior intelligence. However, his natural disposition is sickly and quiet. He primarily uses poison and firearms for assassinations. He speaks politely.