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|Died||December 1, 1602 (aged 24 or 25)|
|Allegiance|| Mōri clan|
Saemon no Kami (左衛門督)
|Commands held||Naval Commander, General|
|Battles/wars||Battle of Sekigahara (1600)|
|Relations||Father: Kinoshita Iesada|
Mother: Sugihara Ietsugu's daughter (杉原家次娘)
Foster Father: Toyotomi Hideyoshi
Foster Father: Kobayakawa Takakage
Wife: Komahime, Shishido Motohide’s daughter
Son: Hashiba Hideyuki
He was adopted by Hideyoshi and called himself Hashiba Hidetoshi (羽柴 秀俊). He was then again adopted by Kobayakawa Takakage, becoming Kobayakawa Hidetoshi (小早川 秀俊). He then renamed himself Hideaki (秀秋) after Takakage's death. Shortly after the Battle of Sekigahara, he renamed one last time to Hideaki (秀詮). Because he had gained the rank of Saemon no Kami (左衛門督) or in China Shikkingo (執金吾) at genpuku and held the title of Chūnagon (中納言), Hideaki was also called Kingo Chūnagon (金吾中納言).
During the Battle of Keicho he led reinforcements to rescue Ulsan Castle from the Ming army. Fighting on the front line with a spear, he managed to capture an enemy commander and broke the siege. However, Hideyoshi saw the danger of a reckless charge by the general commanding an army and deprived him of his domain, Chikugo after returning. Kobayakawa, angered by this, believed the lie circulated by Tokugawa Ieyasu that this had been the doing of a jealous Ishida Mitsunari. He never forgot nor forgave Mitsunari and worked to undermine his position. Moreover, Kobayakawa was known to attack women and children during the campaign, an act that is despised by many of his fellow commanders.
Before the battle of Sekigahara, Kobayakawa happened to be in Osaka and acted as though he would go along with Mitsunari, even though he had intended to betray him, having secretly communicated with Ieyasu. Knowing Kobayakawa held ill feelings, Mitsunari and Ōtani Yoshitsugu promised him two additional domains around Osaka and the position of kampaku (until Toyotomi Hideyori grew old enough to rule) if he helped them to victory.
Even after the battle began, Kobayakawa kept his intentions hidden. Ieyasu's force (east) was not faring well against Mitsunari from the west; Ukita Hideie was winning against Fukushima Masanori and Ōtani Yoshitsugu was also winning against Tōdō Takatora. Kobayakawa was hesitant to participate with either side. Ieyasu ordered troops to fire blanks against the Kobayakawa troops to force them into action. Kobayakawa then ordered an attack on the Otani troop and while this attack was beaten back temporarily, his action forced the other armies who had pledged betrayal to also turn. The battle was over within a day.
Kobayakawa also had success in the mopping up operations that followed, defeating Mitsunari's father, Ishida Masatsugu in the siege of Sawayama. Once the dust had settled, Kobayakawa was given the defeated Ukita clan's former fiefdoms of Bizen and Mimasaka, for a total of 550,000 koku. However, Kobayakawa suddenly died two years later after supposedly going mad, and with no one to succeed him, the Kobayakawa clan disbanded, and his fiefdoms were absorbed by the neighboring Ikeda clan.
Media related to Kobayakawa Hideaki at Wikimedia Commons