Xiang Yu was a native of Xiaxiang, his given name being Yu. When he first rose in revolt, he was twenty-four. His uncle Xiang Liang—younger brother of Yu's father—was the son of Xiang Yan, the Chu general whom the Qin general Wang Jian had slain. The Xiang family had served as Chu generals for generations and had been enfeoffed at Xiang, which is how they took their surname.
In his youth, Xiang Yu studied letters but gave them up before mastering them. He then took up swordsmanship and failed at that too. Xiang Liang flew into a rage. "Letters are only good enough to record a name," Yu replied. "A sword can only defeat one man—there is no point learning it. What I want to learn is how to defeat ten thousand men." So Xiang Liang taught Yu military strategy. Yu was overjoyed but grasped only the general outline and refused to pursue it further.
Once, when Xiang Liang faced arrest in Liyang, he asked the prison clerk Cao Jiu to write a letter to the Liyang prison clerk Sima Xin, and the matter was quietly dropped. Xiang Liang had committed murder, so he and Yu fled to Wu to escape vengeance. The gentry and officials of Wu all ranked below Xiang Liang. Whenever Wu undertook major construction projects or funerals, Xiang Liang invariably took charge, secretly organizing guests and young men on military principles—so everyone came to recognize his ability.
As the First Emperor of Qin crossed the Yangtze during his inspection tour of Kuaiji, Xiang Liang and Yu observed the imperial procession side by side. "I could replace him," Yu declared. Xiang Liang immediately clamped a hand over Yu's mouth. "Never say such a thing again—you would bring destruction upon your entire clan!" Yet Xiang Liang became convinced that Yu was no ordinary man. Yu stood over eight feet tall, could hoist a cauldron with ease, and possessed talents that far surpassed others. Even the finest young warriors of Wu had come to fear him.
In the seventh month of the second year of Qin Er Shi, Chen Sheng and others rose in revolt at Daze. In the ninth month, the Kuaiji prefect Tong said to Xiang Liang: "The lands north of the Yangtze have risen in rebellion—this is surely the moment heaven sends to destroy Qin. I have heard that he who strikes first controls others, while he who strikes second is controlled by them. I wish to raise an army, with you and Huan Chu as commanders." At that time Huan Chu was a fugitive hiding in the marshes. "Huan Chu has fled," said Xiang Liang, "and no one knows where he is—only Yu knows his whereabouts." Xiang Liang went out and told Yu to wait outside with sword drawn. He then re-entered and sat down with the prefect. "If you would summon Yu," he said, "so that he may receive your orders and summon Huan Chu." "Agreed," said the prefect. Xiang Liang called Yu in. A moment later, Xiang Liang gave Yu a meaningful look: "Now!" Yu drew his sword and struck off the prefect's head. Xiang Liang held the head aloft, displaying the official seal and insignia. The household dissolved into chaos. Yu cut down several dozen men. Terror struck the residence; no one dared move. Xiang Liang then called together his most trusted and bold officers, explained his intentions, and raised an army in Wu.
He sent men to recruit from the neighboring counties, gathering eight thousand picked troops. He appointed leading gentry of Wu as captains, company commanders, and battalion officers. One man was passed over and appealed to Xiang Liang. "Recently, when someone died," Liang replied, "I assigned you certain duties, and you could not discharge them. That is why I am not using you." Everyone thereupon fell in line.
Xiang Liang was appointed military governor of Kuaiji, with Lü Jia as his deputy general, and they set about conquering the surrounding counties. A man from Zhaoping of Guangling had been campaigning for King Chen in Guangling but could not take the city. Hearing that King Chen had been defeated and had fled, and that Qin troops were approaching, he crossed the Yangtze. Claiming to carry orders from King Chen, he installed Xiang Liang as Supreme General of Chu. "The East has been pacified," he declared. "Move your forces swiftly westward to strike Qin."
Xiang Liang crossed the Yangzi River with eight thousand men, heading west. Learning that Chen Ying had seized Dongyang, he dispatched an envoy proposing they join forces and march westward together. Chen Ying had served as a clerk in Dongyang county, renowned for his integrity and prudence, and held in respect as an elder. The young men of Dongyang had killed their magistrate and gathered several thousand followers, seeking a leader but finding none worthy. They approached Chen Ying, who declined. They then compelled him to accept command, and twenty thousand men from the county rallied to his cause. The young men wished to proclaim Chen Ying king, establishing a distinct force distinguished by black headbands. Chen Ying's mother said to him: "Since I married into your family, I have never heard of your ancestors attaining honor. To gain great fame so suddenly is ill-omened. Better to attach yourself to another. If you succeed, you may still earn a title; if you fail, you can easily escape—you will not be singled out by the world." Chen Ying dared not become king. He said to his officers: "The Xiang family has produced generals for generations and is renowned in Chu. If we wish to undertake a great enterprise, we must follow the right man. With such a distinguished lineage to rely upon, we will surely destroy Qin." They followed his counsel and submitted to Xiang Liang.