In Chinese history, the intellectuals in the difficult times of transition usually suffered a double loss. They lost both their native lands and their poetic visions or source of inspiration. The scholar-poet Shih Shih-chi’s woeful life marked by vicissitudes is an apparent example. Shih was a native of Taiwan. He had been the leading figure in the community of poets and enjoyed a pleasurable life before China ceded Taiwan to Japan and he was forced to leave for the Mainland. There he appeared to be a hopeless wanderer. His miserable life is reflected in his latter-day poetic work. The main concern of this paper is to present the profile of a typical Taiwanese poet facing the disastrous times of transition.