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Born in 1568 as the son of Hideyoshi's elder sister Nisshu-ni, his childhood name was Mago-Shichiro. Adopted by Hideyoshi, in the Battle of Komaki-Nagakute in 1584 he suffered a major defeat against the combined forces of Oda Nobuo and Tokugawa Ieyasu in his first battle. However, he subsequently distinguished himself in the Shikoku, Kyushu, and Odawara campaigns. In 1591 he took over the position of Kampaku as Hideyoshi's designated successor. He was also a cultured man who loved linked verse and tea ceremony, known for governing well including developing the castle town of Omi-Hachiman. However, with the birth of Hideyoshi's biological son Hideyori in 1593, his position as heir became unstable. In 1595 he was accused of treason, confined to Mount Koya, and forced to commit seppuku. About 30 family members including his principal wife, concubines, and children were executed at Sanjo Riverbed, branding him the "Murderous Regent." However, recent scholarship has reassessed much of the accusation against Hidetsugu as false, reinterpreting the tragedy as a product of Hideyoshi's paranoia. He was 28.

A cultured man skilled in both letters and arms, who loved linked verse and tea ceremony. Kind to his retainers, yet powerless against his uncle Hideyoshi's suspicion.

Much of the "Murderous Regent" infamy was later fabrication; he was actually a capable ruler who brought prosperity to Omi-Hachiman. The Hidetsugu Incident symbolizes the self-destruction of the Toyotomi regime.