Takatsugu Kyogoku was from Wakasaka Province, and was the head of the Kyogoku clan. He married Lady Ohatsu, daughter of Nagamasa Asai and the niece of Nobunaga Oda, making his bonds with the family stronger. Also, he became the brother-in-law of Hideyoshi Hashiba when Hideyoshi married Ohatsu's older sister Lady Yodo. Also, Ohatsu's sister Lady Oeyo married Hidetada Tokugawa, making Takatsugu and Hidetada also brothers-in-law. However, in 1598, he sided with the anti-Tokugawa Western Army after Hideyoshi's death, and Takatsugu ran Otsu Castle for the Toyotomi. But he later changed his mind and sided with Ieyasu Tokugawa's Eastern Army, and fell under attack at Otsu by Sakon Shima's Western Army troops. Takatsugu Kyogoku surrendered, but he regained the castle after the Battle of Sekigahara and was entrusted with the fief of Obama Castle. He died in 1609.