Enya Takakiyo served as head of the Enya clan in Tajima Province based at Ashiya Castle. The Enya of Tajima originated from the Enya clan in Izumo. Takakiyo received the title of Suō no kami. Kami was designated the highest of a four-level rank for kokushi, or officials serving as local commissioners on behalf of the central authorities in Kyōto.
Takakiyo had intimate knowledge of the convoluted mountainous terrain, positioning soldiers in unexpected places. Takakiyo drew comparisons to Nasa Nihonnosuke, a leader of pirates originating from a branch of the Kusakabe clan in Tajima. Hideyoshi referred to them as sanzoku, or pirates based in the mountainous areas who attacked and robbed those passing through their territory. The presence of these groups posed an uncertain and potentially fatal risk to travelers during the Sengoku period.
Takakiyo indicated a desire to pledge allegiance prior to an attack into Tajima by the Amago and Oda. Later that year, Takakiyo’s collusion with Yamana Toyokuni invited an attack by Takeda Takanobu, which Takakiyo repelled. He then came under the command of the Mōri. From 1574 to 1576, Takakiyo protected Takanobu despite their earlier conflict, and pleaded with the Mōri to spare Takanobu’s life and reinstate him. These wishes proved to no avail after Toyokuni assassinated Takanobu, whereupon Takakiyo fled to Ashiya Castle without attempting to resist the Oda invasion.
Surrounded on all sides by precipitous seaside cliffs, Ashiya Castle stood as a naturally impregnable fortress. Its location enabled control over the nearby sea lanes. In 1580, Hashiba Hideyoshi attacked Tajima, and Ashiya was captured. Takakiyo fled to the protection of Kikkawa Tsuneie, a retainer of the Mōri, head of the Kikkawa clan of Iwami, and lord of Tottori Castle in Inaba Province. In 1581, Takakiyo joined forces led by Tsuneie at Tottori to oppose the Oda campaign in the western provinces under the leadership of Hideyoshi.
Takakiyo built Kariganeyama Castle on Mount Karigane to the north of Tottori Castle and, together with Maruyama Castle under the control of the Nasa, was in charge of the supply lines for Tottori. Rather than a direct assault on the castle, Hideyoshi adopted a plan to wait until their supplies ran out. Having determined this could be hastened by cutting the supply lines from Kariganeyama and Maruyama to Tottori, Hideyoshi ordered Miyabe Keijun to attack Kariganeyama Castle. Takakiyo fought valiantly against Keijun’s men, but supply shortages undermined the defenders, and as the castle fell to the Oda, Takakiyo escaped to Maruyama Castle.
Soon thereafter, Tsuneie’s men in Tottori Castle confronted a hellish starvation, whereupon he offered to surrender to Hideyoshi on the condition that he be allowed to sacrifice himself in exchange for having the lives of his men spared. While Hideyoshi respected Tsuneie’s courage and planned to spare him, he scorned the actions of Takakiyo and Nihonnosuke as those of pirates and resolutely insisted that each of them commit seppuku. Takakiyo and Nihonnosuke then committed seppuku in their quarters prior to Tsuneie taking his own life. Memorial towers for Takakiyo and Nihonnosuke stand at the western base of Maruyama Castle.