Shigetsugu was on the side of the western army in the Sekigahara Battle in 1600, and became a commander in chief after conquering the Tanabe-jo Castle in Tango (Maizuru-jo Castle), but when the western army was completely defeated in the main battle, he was tracked down by Tadaoki HOSOKAWA of the eastern army, and killed himself.
重次は慶長5年（1600年）の関ヶ原の戦いにおいて西軍に味方し、丹後田辺城（舞鶴城）の城攻戦総大将となるが、本戦で西軍が壊滅すると東軍の細川忠興の追討を受けて自害した。