He was a half-brother of Toyotomi Hideyoshi,[1] one of the most powerful and significant warlords of Japan's Sengoku period and regarded as 'Hideyoshi's brain and right-arm'.

He led Hideyoshi's vanguard force a few years later into Satsuma Province, contributing heavily to his half-brother's victories in gaining control of Kyūshū.

Hidenaga was awarded the provinces of Kii, Izumi and Yamato, reaching a governance of one million koku.

During the Warring States period, it was not uncommon for even parents and siblings to engage in lethal conflicts, yet he unwaveringly supported his brother.

Indeed, Hideyoshi's Korean campaign and the purge of Hidetsugu occurred after the deaths of Hidenaga and Sen no Rikyū.