Born Dai Chunfeng, he was just four years old when his father died, leaving his mother to raise him. At the age of six, Dai was enrolled in a private academy the Linsen elementary school, to study Chinese classics; he later graduated as
valedictorian from
Wenxi County Elementary School. His mother could not afford to send him to university, so at the age of 16 he had to leave home and make his own way in the world. With no steady income or guidance, he began living on the streets of
Shanghai. Until 1923, he was mentored by labor organizer and hitman
Wang Yaqiao. Dai Chunfeng soon became a skilled gambler who could often be found in one of Shanghai's many casinos, trying to win enough money to make ends meet. It was in a Shanghai casino that he met
Du Yuesheng, head of the criminal organization known as the "
Green Gang". Through Du Yuesheng, he later met
Chiang Kai-shek. It is unclear when Chiang and Dai first met, but it was probably around 1921. Dai later lost all his money and was forced to return to Bao'an. In 1927, Dai met his elementary school friend
Mao Renfeng, who suggested that Dai enroll in the Whampoa Military Academy in
Guangzhou, where Chiang served as Superintendent-Commandant (1924–1947). Dai followed the suggestion, obtained a letter of recommendation from Du Yuesheng, and made his way to Guangzhou. In 1925, Dai enrolled in the 1st Student Regiment of the Sixth Class of the
KMT Officer Training Academy. At this time, he changed his name to "Dai Li," which in
Chinese refers to an assassin's hooded veil, reflecting the clandestine nature of his planned future career. Chiang soon made him a student informant to spy on Communist activities within the academy, where he played an instrumental role in the
Zhongshan Warship Incident of March 1926. ==Role in KMT==