The person who was surprisingly more of an underdog than Liu Bei from the Three Kingdoms.

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Liu Bang, the ancestor of Liu Bei. Liu Bang's family was actually better off than Liu Bei's, but Liu Bang himself was just a local bum. Surprisingly, many of Liu Bei's core ministers weren't actually from commoner backgrounds. However, except for Zhang Liang, most of Liu Bang's core founding members were from very lowly or average backgrounds. Even the 'high-ranking' ones were just local low-level clerks like Xiao He. Han Xin was from a poor family, and guys like Fan Kuai and Xiahou Ying were just regular dudes from the same neighborhood who became founding heroes just by hanging out with Liu Bang... And Liu Bang's enemy was...

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Xiang Yu, the strongest being in Chinese history. Even Han Xin, one of history's greatest strategists, got wrecked by Xiang Yu and avoided direct confrontation—even in historical records, Xiang Yu is described as a literal natural disaster. Liu Bang basically never won a proper fight against an army led by Xiang Yu until the very last battle, and even then, Xiang Yu managed to escape... Liu Bang is the guy who kept losing and losing but tanked everything until he finally unified China.