He then became a member of the Oda clan and was ordered to serve under Kinoshita Tōkichirō (the eventual Toyotomi Hideyoshi).

Hidehisa is generally described as a brave and skillful warrior in his early days with Nobunaga; he was often at the front lines of the Oda clan's military operations.

He also appears to have inherited some of Hideyoshi's charisma, as he was able to avoid getting himself killed despite ending up several times in situations that would normally have boded poorly for most samurai.

[1] Due to this series of events, after Hideyoshi's death, Hidehisa easily sided with Ieyasu in the Sekigahara campaign.

In 1600, Hidehisa was in the army of Ieyasu's heir, Tokugawa Hidetada, they were unable to reach the Sekigahara main battle in time due to the stalling tactics of Sanada Masayuki at Siege of Ueda.