Hidemasa and his eldest son, Tadanaga OGASAWARA died at Osaka Natsu no Jin (Summer Siege of Osaka) of the Siege of Osaka and because the eldest son of Tadanaga, Nagatsugu OGASAWARA was still a child, the second son of Hidemasa, Tadazane OGASAWARA took over the position as head of the family.
秀政と長男の小笠原忠脩は慶長20年（1615年）の大坂の役大坂夏の陣で討死し、忠脩の長男の小笠原長次は幼年であったため、秀政の次男の小笠原忠真が家督を相続した。