Throughout his life, Cao Cao formed deep friendships with many individuals, though due to various reasons, he also fell out with numerous close friends, ultimately becoming mortal enemies. Among those who eventually turned against him, Zhang Miao and Yuan Shao are two poignant examples.
Early friendship and loyalty
In his youth, Zhang Miao was known for his chivalrous spirit, often aiding the poor and helping others, earning the admiration of many warriors. He was listed as one of the “Eight Compassionate Men” (meaning those who used their wealth to save others), alongside figures like Du Shang and Wang Kao. Cao Cao and Yuan Shao, who admired such virtues in their youth, deliberately sought his friendship, and the three gradually became close companions, with Zhang Miao and Cao Cao sharing the strongest bond. Due to his reputation, Zhang Miao was summoned to serve in the government, rising to the positions of Governor of Chenliu.
After Cao Cao raised an army to oppose Dong Zhuo, Zhang Miao devotedly followed him, remaining loyal even during Cao Cao’s most difficult times.
In 193 AD, before embarking on a campaign against Tao Qian, Cao Cao told his family, “If I do not return from this battle (meaning if I die), you can seek refuge with Mengzhuo (Zhang Miao’s courtesy name).” Zhang Miao tearfully accepted this responsibility. When Cao Cao returned victorious, the two met and wept together, rejoicing in their reunion. Their closeness was evident from such moments.
The cracks in the friendship
Surprisingly, this intimate relationship eventually shattered. Zhang Miao not only betrayed Cao Cao but nearly cost him his base of power. The reasons for his betrayal were numerous and complex, but two incidents served as critical triggers.
Cao Cao’s execution of Bian Rang
Bian Rang was a renowned scholar and former high-ranking official known for his pride and talent. He frequently belittled and mocked Cao Cao’s background, character, and reputation, gradually becoming a thorn in Cao Cao’s side. Around 193 AD, Cao Cao ordered Bian Rang to be executed.
In Cao Cao’s eyes, executing Bian Rang was like crushing an insect—a means to intimidate others. However, instead of serving as a warning, the act revealed Cao Cao’s cruel nature, inciting anger among the scholars and people of Yanzhou.
The massacre of Xuzhou’s civilians
While campaigning against Tao Qian, the Governor of Xuzhou, Cao Cao unleashed indiscriminate slaughter upon the civilians. The conflict originated when Tao Qian, seeking to foster goodwill with Cao Cao, sent his general Zhang Kai to escort Cao Cao’s father, Cao Song, and his family through Xuzhou. However, Zhang Kai killed Cao Song and stole his wealth. Although Tao Qian may not have intended the murder, he bore responsibility as Zhang Kai was his subordinate. Cao Cao vowed revenge for his father’s death.
Under the pretext of avenging his father, Cao Cao launched a military campaign against Tao Qian, directing his rage against the civilians of Xu Province. Wherever his troops marched, they massacred cities, resulting in the deaths of over 100,000 innocent people.
Cao Cao’s rise to the governorship of Yan Province (Yanzhou) owed much to the efforts of Chen Gong, Bao Xin, Zhang Miao and others, who had seen him as a heroic savior. Witnessing his descent into a bloodthirsty tyrant caused them immense anguish. To save the people of both provinces and halt the violence, Zhang Miao and his allies resolved to break with Cao Cao and seek a new leader.
The betrayal and its aftermath
The following year, while Cao Cao was campaigning in Xu Province for the second time, Zhang Miao and Chen Gong staged a rebellion in Yan Province, welcoming the fugitive Lü Bu as the new governor. Nearly all commanderies joined the revolt, leaving only Fan County, Dong’e, and Juancheng under Xun Yu and Xiahou Dun’s control to maintain Cao Cao’s foothold. Cao Cao fought fiercely against Lü Bu for two years before achieving a decisive victory at Juye and reclaiming his territory.
After his defeat, Lü Bu fled to Liu Bei, who had just been promoted to Governor of Xu Province (Xuzhou). Zhang Miao, knowing he would not be forgiven by his old friend, followed Lü Bu eastward but left his family in Yongqiu under his brother Zhang Chao’s care. Consumed by hatred, Cao Cao besieged Yongqiu, massacred its inhabitants, and executed Zhang Chao and Zhang Miao’s family.
The tragic end
Upon learning of his family’s fate, Zhang Miao wept in despair. He led his remaining troops to seek aid from Yuan Shu, requesting support to attack Cao Cao. However, he was killed by his own soldiers en route, never fulfilling his goal.
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