It is well known that Song neo-Confucians’ critiques of the eight great prose masters of the Tang and Song dynasties were generally in the manner of Confucian in-house controversies. However, due to the strict barriers to its “Dao Xue”, conflicts were inevitable. Zhu Xi scribed profound critiques of the eight great prose writers at times on the basis of his credentials as the compiler of a prodigious volume of neo-Confucian learning, and at times as a literary critic. Han Yu, Ouyang Xiu and Su Shi were the subjects of the majority of his criticisms, and generally speaking, critiques stemming from Zhu’s credential as a neo-Confucian scholar were generally critical in nature, while those made as a literary critic were more often than not commendatory. However, Zhu Xi appeared to have a special preference for the writings of Zeng Gong, and hardly raised any opinions that were critical of them. This paper undertakes a detailed analysis of Zhu Xi’s multifaceted appraisals of Zeng Gong in order to understand the various layers of meaning presented in Zhu Xi’s critiques.