Takasuke was short of recovering his fief Mitoya, and left the Mori clan to be a vassal of the Hosokawa clan; during the Battle of Sekigahara in 1600, he joined the army locking itself up in Tanabejo Castle in Tango Province and where he provided exemplary service.
しかし、本領である三刀屋の回復には至らず、毛利氏を退去して細川氏に仕え、慶長5年（1600年）の関ヶ原の戦いでは丹後国田辺城(丹後国)籠城に加わり活躍した。