After Qin Shi Huang's death in 210 BC, however, there were revolts everywhere against his incompetent son and successor Ying Huhai (Qin Er Shi). Many of these revolts claimed to be attempts to restore the kingdoms that Qin had conquered two decades earlier. One of these rebellions started in 209 BC, under Xiang Liang. At that time, the Xiangs were living in the region of Wú (modern southern Jiangsu). Xiang Liang was well known as the descendant of the Chu general Xiang Yan, and people of the Wu region quickly rallied about him in resistance to Qin. After one of the first and strongest rebel generals, Chen Sheng, then styling himself the Prince of Chu, was assassinated by one of his guards, Xiang Liang assumed leadership of a coalition of rebels. Serving under his uncle, Xiang Yu showed quickly both his military ingenuity and his ruthlessness. For example, when his uncle commissioned him to attack the Qin stronghold Xiangcheng (襄城, in modern Xuchang, Henan), he conquered the city despite its strong defenses, and after it fell, he slaughtered the entire population.
To rally the disparate forces against Qin, Xiang Liang reinstated the Chu monarchy and installed a member of the deposed Chu royalty, Mi Xin (羋心), as the Prince of Chu in 208 BC. Initially, under Xiang Liang's control, Mi Xin was more or less a puppet prince. However, when Xiang Liang died in battle later that year, there was no single general who took his place, and the rebel Chu's generals and the Prince became an effective collective leadership, with the Prince gradually asserting his authority. A demonstration of this was that, against Xiang Yu's wishes, in winter 208 BC, he sent Xiang Yu as the second-in-command to Song Yi (宋義) in an expeditionary force to relieve Zhao Xie (趙歇), the Prince of Zhào, who was then under resurgent Qin siege by Qin general Zhang Han in his capital Handan (in modern city of the same name in Hebei). He put Liu Bang in command of another expeditionary force (which Xiang had wished to command) against the heart of Qin itself. Around this time, Prince Mi Xin also named Xiang the Duke of Lu.
Xiang quickly marched toward Handan. At the time of his arrival at the battlefield, the city of Julu and the Zhao forces within had been nearly starved by the besieging Qin forces, under general Wang Li (王離), an assistant to Zhang Han. Xiang understood the importance of reducing the Qin forces' effectiveness first, and he accomplished this by cutting off Wang's supply lines. To further prevent Wang Li from using his weakness as a source of motivation for his army, Xiang Yu ordered his forces to carry three days of supplies and destroy the rest, giving his troops the option of quick, decisive victory or death. Still, no other relief force sent by other rebel principalities dared to engage the Qin forces, and Xiang attacked them alone. He fought nine engagements before the Qin forces collapsed and Zhang was forced to retreat. Wang was captured. After the battle, all other rebel generals, regardless of whether they came from Chu or not, were so awed by Xiang, that they voluntarily came under his command. Xiang then prepared for a final confrontation with Zhang.
That confrontation would not happen, however. The Qin prime minister, the eunuch Zhao Gao, had become jealous of Zhang's military successes and became concerned that Zhang would replace him. He falsely accused, before Qin Er Shi, Zhang of military failure and conspiracy with the rebels. Having no other option, Zhang surrendered to Xiang without a fight in summer 207 BC. Xiang slaughtered the surrendering Qin army except for Zhang and a few other generals, and, ignoring Prince Xin, named Zhang the King of Yong (a region within Qin proper (i.e., the former territory of Qin during the Warring States Period before its expansion), modern central Shaanxi), even though he had not yet captured Qin proper.
Under a promise issued by Prince Xin of Chu earlier, Liu Bang had assumed that he, as the one who entered Xianyang first, would be created the Prince of Guanzhong (which includes the capital Xianyang and most of Qin proper). He had also planned to make Ying Ying, whose wisdom and knowledge he admired, his prime minister. Xiang paid no attention to Liu's presumptive title to Qin, and he, in another act of deliberate cruelty, killed Ying Ying. It is also generally believed that he burned down the Qin palace, which contained a large royal library commissioned by Qin Shi Huang. The unique copies of many "forbidden books" were then lost forever. However, recent reports from historians said that Xiang Yu did not burn down the Qin Palace. Despite advice from one of his advisors to set his own capital at Xianyang, Xiang was intent on returning to his home region of Chu. Xiang said "To not return home when one has made his fortune is like walking in the night with rich robes, who will notice?" (富贵不归乡，如锦绣夜行，谁知之尔?). In which one of the advisors muttered "Those men of Chu are nothing but apes wearing robes", when Xiang Yu heard that insult he made sure that advisor was executed by being boiled alive slowly.
Note: Yong, Sai, and Zhai were known as the Three Qins because they comprised of the former territories of Qin proper; similarly, Qi, Jiaodong, and Jibei were known as the three Qis.
The five year power struggle between Xiang and Liu became known as the Chu Han Contention. Initially, Xiang had all the advantages -- he had the much larger territory, the larger army, and the greater number of allies. He was also a far superior military commander than Liu. However, his lack of political skills, the inability to accept criticism, and his inability to trust and to listen to his advisors would eventually lead to his downfall. He also paid little attention to supplies for his army -- a fatal error, as Liu set up an efficient army supply system to keep his army well-fed and well-clothed with food and clothing shipped to the front from his heartland, while Xiang's army eventually fell apart from hunger and lack of weaponry. As he got bogged down in various wars on different fronts, Liu, along with his very able general Han Xin, was able to gradually absorb many of the principalities into his territories or alliance. By 203 BC, the balance had shifted against Xiang. Xiang Yu, however, managed to capture Liu Bang's father after a year-long siege. Outside the city walls, Xiang Yu threaten to boil Liu Bang's father alive if Liu Bang did not surrender. Liu Bang remarked, "We were sworn brothers, and my father would be your father" and then responded, "When you are done with our father, let me have a taste of the soup." Xiang Yu instead sued for peace, and Liu entered into a treaty with Xiang. However, as soon as Liu received the hostages that Xiang returned to him as part of the treaty, Liu discarded the treaty and attacked Xiang's army which were completely unprepared for the attack. In 202 BC, his forces, under Han Xin's command, had Xiang trapped at the Battle of Gaixia. Liu ordered his army to sing songs from Xiang's native country of Chu to give Xiang's soldiers an impression that they were fighting against their own countrymen, which demoralized Xiang's army. Xiang Yu, sensing his first defeat in his military career, became distraught and sang to his beloved concubine Yuji (虞姬) who was with him in the camp:
To which Yu Ji replied after performing a final dance in front of him:
Yu Ji then committed suicide. (The title of the famous Chinese opera "Farewell My Concubine", as well as the 1993 film inspired by the opera, comes from the aria that Xiang Yu sings to Yuji before his last stand.)
Early next morning, Xiang Yu organized his troops for a last desperate charge to escape the encircling Han troops. Xiang still enjoyed support in his homeland in the Wu region, south of the Yangtze River. He, with a handful of his personal cavalry, finally managed to break out, and headed for the river, intending to cross it at Wujiang (烏江, in modern Chaohu, Anhui). The fordsman at the river encouraged him to cross, telling him that the people of Wu were still intent on supporting him as their prince. Xiang laughed and said "Heaven wants me dead, why should I go back?". He then committed suicide. According to legend, he cut his throat open with his own sword.
There are many different stories about Xiang Yu's suicide. One famous story is when he was surrounded by Han cavalry, he saw an old friend and said "Are you Lü Matong? I heard the Prince of Han has a great reward for my head. Here let me give you this..." After saying these words, he killed himself. (A legend indicates that he decapitated himself with his own sword, although many dispute whether such a thing is possible.) Another legend about Xiang Yu as a warrior was that he and his remaining 28 personal elite bodyguards managed to slay more than 200 Han cavalry soldiers. His bodyguards fought to the bitter end and only 2 of Xiang Yu's soldier died in battle, and there was a man with a ship waiting for him. He said that he would die fighting and ordered all his elite bodygaurds to leave. After they had gone, Han soldiers surrounded him, but none dared to approach the heavily injured Xiang Yu, who instead he committed suicide upon seeing Lu Matung among the Han forces.
A fight apparently broke out among Han's troops at the scene over Xiang's body because of the large reward offerred by Liu Bang. According to historians, Xiang's body was severely mutilated in the fight and the reward had to be divided five ways.
Although Liu Bang was a bitter rival, he made a grand funeral (with the ceremony befitting that of a duke) and graveyard for Xiang Yu and had it maintained regularly. Also, Liu spared many of Xiang Yu's relatives and rewarded Xiang Bo, who saved Liu Bang's life during the Feast at Hong Gate incident, by creating him and three other relatives of Xiang Yu marquesses.
Xiang's heroism on the battlefield and his death at the hands of Liu Bang has been immortalized in the Shǐjì ("Records of the Grand Historian") has made him a cultural hero in Chinese folk tales and poetry, the warrior king, Xiang Yu's battle against the people's king, Liu Bang. His dominance over the princes were undeniable, credited with all the victories by himself and defeated every single opponent in combat. Even Han Xin, one of the greatest commanders in Chinese history who was given the title 'Invincible Against Metal' by Liu Bang, knew of Xiang Yu's invincibilities, and never really confronted him in battle. Instead Han Xin used the strategy of isolating Xiang Yu, which Liu Bang took advantage of, and betrayed Xiang Yu on the peace treaty.
The stories of prophecy flourished and in some ways overshadowed Liu Bang's glory of building the Han dynasty. During the period of war between Liu Bang and Xiang Yu, Liu Bang had once asked Han Xin, "How many soldiers can you command with efficiency?" Han Xin replied, "As many as possible -- my strength can only be increased by the number of soldiers I command." Liu Bang then asked Han Xin, who had served under Xiang Yu but was driven out, "what is Xiang Yu's weakness? Is there a way to defeat him?" Han Xin calmly replied, "No, Xiang Yu himself is invincible, he is destined to be king." Liu Bang however had a different destiny: the destiny of becoming an emperor.
Xiang Yu is popularly viewed as possessing great bravery but lacking in wisdom, as summarized in the Chinese idiom "yǒuyǒng wúmóu" (有勇無謀). His military tactics were required learning for generals, while his political blunders were also required learnings for emperors as to what not to do as leaders. An idiom that referred to his being surrounded at Gaixia is "surrounded by Chu music" (sìmiàn Chǔgē, 四面楚歌), which refers to a desperate situation without allies--based on Xiang's lament at Gaixia that he heard Chu songs coming out of Liu's surrounding camps--implying that Liu had conquered all of Chu. Yet another idiom that refers to the inability to listen to advice is, "having a Fan Zeng but unable to use him" (有一范增而不能用), referring to Xiang's reliance on Fan but actual inability to listen to Fan's advice, which came out of Liu's critique of Xiang after his final victory. (For the more complete quote from Liu, see here.)
Another figure in Chinese history, Sun Ce, was often compared favorably to Xiang by his contemporaries, and was given the nickname "Young Conqueror" (Xiǎo Báwàng 小霸王).
He is depicted as a ruthless leader, making a sharp contrast with his rival, Liu Bang. He was known to be a mass murderer starting from the battle of Julu. On the other hand, Liu Bang is depicted as a shrewd and cunning leader, who strictly ordered his troops not to loot in the cities they conquered to gain the support and trust from the people, which Xiang was not able to do. As the story goes, it was Xiang's biggest mistake as a leader; it soon became an example for Confucianists to say that leaders should rule with love, but not fear.
Xiang Yu appeared in several movies, video games, and also comics. He is often depicted as heroic and brave in battle but arrogant and bloodthirsty in domestic issue; and toward other people, he is an early example of a Chinese tragic hero.
The Meng Ch'iu, an eighth-century Chinese primer, contains the four character rhyming couplet "Zhi Xin impersonates the Emperor", referring to an episode in which Zhi and two thousand women disguise themselves as Liu Bang and an army, distracting Xiang Yu while Liu Bang can escape from the city of Jung-yang.