The evaluations of past generations on Sir Wang Jing, mostly in historical biographies, jottings, and short stories, lead to both positive and negative comments and have established a three-dimensional image of Sir Jing. However, there is yet no monograph on poetry, which is also one of the important genres in the writing system of stories about Sir Wang Jing. This article attempts to explore the discussions of figures in history-themed poems and to return to the beginning of the arguments on Sir Jing’s image and depict the image of him portrayed in Song poems. First, it discovers the polarized identity, as a prime minister with loyalty or a guilty person causing the ruin of the Song dynasty. Second, it organizes and analyzes the common materials and theme thoughts in writings about Sir Jing, such as creating atmosphere of elegies around tombs and shrines and fickleness of the world, sketching the reading hall and mocking new learning, and paying attention to inscriptions of calligraphic works and paintings and admiration for the past manner. Finally, it probes into the rhetoric of Song people’s writings about Sir Jing. For example, the structure design of opposition between one and many and expansion and contraction of time-space helps to highlight the effect of sighs with emotions. To give another example, the adjusted use of the words of Sir Jing’s poems adds new meanings to their original meanings. To sum up, this article exhibits vividly on paper the Sir Jing in Song poems and provides a reference for studies on the image of Sir Wang Jing shaped by history.