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Background and early life (155–184)

Cao Cao's ancestral home was in Qiao County (譙縣), Pei State, which is present-day Bozhou, Anhui. He was purportedly a descendant of Cao Shen, a statesman of the early Western Han dynasty (206 BCE – 9 CE). His father, Cao Song, served as the Grand Commandant during the reign of Emperor Ling (r. 168–189), buying his way into high government office for an exorbitant sum, and serving less than half a year. Cao Song was a foster son of Cao Teng, a eunuch who served as a Central Regular Attendant and the Empress's Chamberlain under Emperor Huan (r. 146–168), and held the peerage of Marquis of Fei Village (費亭侯).

In his youth, Cao Cao was known to be perceptive and manipulative. He liked to hunt, idle, roam about freely, and play vigilante so he was not as highly regarded compared to his more studious peers. From the time Cao Cao was fifteen until he turned thirty, widespread epidemic diseases ravaged China on average one out of every three years.

Despite Cao Cao's loafing ways and unimpressive behaviour, there were two persons – Qiao Xuan and He Yong – who recognised his potential and extraordinary talents. Upon visiting the famous commentator and character evaluator Xu Shao, Cao Cao was assessed as being "a treacherous villain in times of peace, and a hero in times of chaos". Another source recorded that Xu Shao told Cao Cao, "You will be a capable minister in times of peace, and a jianxiong in times of chaos."