The acclaimed modern historian Chen Yinke argues that Qian Qianyi’s (15821664) literary criticism on poetry and prose writings consists of two types: One can be considered as literary criticism in the strict sense of the term. Another is, however, infused with political purpose, such as the unjustifiable commendation of the late-Ming poet Cao Xuequan (1573-1646). Chen holds that Qian’s praise of Cao was motivated by political considerations, i.e., to help bring about his release from custody in Nanjing from 1647 to 1649 because of his suspected involvement in an anti-Qing uprising led by Huang Yuqi (1579-1648). This paper unfolds in two parts. First, it conducts a historical investigation of the official career of the chief personages concerned, to critically assess the assumed plausibility of a political bonding among them. When Qian was arrested by the authorities, Cao had already died two years earlier. What was the political use of a dead poet for Qian’s legal defense in the lawsuit? Being intrigued by Chen’s theory, I examine and illustrate the true nature of Qian and Cao’s friendship and their writings on each other. The second part of this paper tries to reconstitute the circumstances in which Qian lauded Cao’s achievements. I argue that Chen’s assertions are problematic, and that Qian had, throughout his long life, admired Cao as a wonderful poet from the Wanli (r. 1572-1620) era. Furthermore, scholars in the past have paid attention only to the role that Cao played in the development of the so-called Min (Fujian) School of Poetry in the late Ming. I nevertheless maintain that Qian’s admiration of Cao should be understood in the light of Cao’s contribution to Nanjing’s extraordinary blossoming of literary clubs and societies in the Wanli era.