Most of the current research on Cheng Shewo has divided his experiences and thoughts into two periods, i.e. , Mainland period and Taiwan period. The current research in the Mainland seldom includes his works produced in Taiwan due to political reasons. By examining Cheng Shewo's works procuded after he left the Mainland, his children's memoirs and Taiwan scholars' research on him, this paper tries to trace his psychological world to reveal the underlying reasons for his going astray as a liberal intellectual in historic transitions.