Based on Zhu Xi’s statement that Laozi’s teachings were very cruel, Wang Fuzhi condemned Laozi as a crafty, petty person in his Confucian commentaries. Yet, he had to understand the Laozi or Daodejing sympathetically when he commented on it in Laozi Yan老子衍 (Extended Commentary on the Laozi). As a result, he showed inconsistency in his criticism and evaluation of the author. Some scholars have noted this problem but have not shed ink analyzing it. This essay finds that Wang Fuzhi’s ambiguous attitude toward Laozi results from his Confucian prejudice against other schools and his failure to grasp the breadth and depth of Laozi’s thought. From the perspective of Heaven, Laozi promoted accommodation and non-interference in self-cultivation and governance, summed up by the maxim that “the sage manages affairs without deliberation, and spreads teachings without words.” In contrast, Wang Fuzhi stuck to the distinction between Confucianism and Daoism, and tried to use humanity and ritual propriety to supplement that which Heaven does not provide; as such, he criticized Laozi as crafty and irresponsible. Wang Fuzhi’s criticism neither hits the mark regarding Laozi’s weakness nor maintains a concordance with his earlier sympathetic appraisal in Laozi Yan; the reason for this is that Wang Fuzhi could not fully grasp Laozi’s thought from a Confucian and anthropocentric perspective.