1540 - 1591
Hidenaga was Hideyoshi's half-brother and a chief retainer, also known as Toyotomi Hidenaga. Hidenaga joined Hideyoshi's staff when the latter took up in Ômi province in 1573 and following Oda Nobunaga's death in 1582 and the defeat of Akechi Mitsuhide was given the fief of Koriyama in Yamato (confiscated from the Tsutsui). Hideyoshi appointed Hidenaga commander of the forces dispatched against Shikoku in 1585, and made him a leading commander (with 60,000 men at his disposal) in the invasion of Kyushu in 1587. Hidenaga was a stolid if unimaginative leader, and advanced slowly despite only desultory Shimazu resistance (save at the one-sided Battle of the Sendai-Gawa). Afterwards, Hidenaga was named Dainogon at Junior Second Rank and an income that may have reached 1,000,000 koku (he also held the title Mino no kami). Well-trusted by Hideyoshi, Hidenaga acted as guardian to the Taiko's infant son Tsurumatsu. When Tsurumatsu died in 1591, Hidenaga stood as the likely heir to his now childless brother. Unfortunately, Hidenaga died that same year of an illness that had plagued him for a number of years, despite the fervent prayers of Hideyoshi and Kyoto's temples. Hidenaga's death was a great source of grief for Hideyoshi, and complicated matters for the Toyotomi, especially coming after the execution of Toyotomi Hidetsugu in 1585.