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The purpose of this study is to examine the life of Wu Wei-ye, who lived in the age of despair in which the dynasty was replaced, and to understand the world of his works. He is a representative poet who played an active role during the Late Ming over to the Early Qing Period. Wu Wei-ye was a leading poet representing drifting people of Ming Period. Therefore, his works have a very important meaning in understanding the poetical circles in Early Qing. In this paper, I first review his philosophy. At his working period, there have been various arguments as to how to accept or reject the literary assertions left by Qianhouqizi(前後七子) , Gonganpai(公安派) and Jinglingpai(竟陵派) of Ming Period. Wu Wei-ye basically succeeded to Fushe(復社) and Jishe(幾社)’s literary assertions and insisted to learn their great literary heritage. Last but not at least, many of his poetry are about social problem, history facts, reproach himself for losing strong conviction and holding an office. Wu Wei-ye’s stands a firm position as a representative poet of early Qing and contributed a lot to the development of Chinese poetry history. Next, I examined & divided his despair-expressing poetry into four(4) categories by their topics : 1) poetry lamenting entering public office and losing his integrity, 2) poetry recalling historic facts 3) poetry singing sadness of losing his country , 4) poetry accusing of social reality.