Instead of assuming “warlords” as a homogeneous counter-force to the May Fourth enlightenment while imagining Chinese intellectuals as a natural alliance for the “anti-warlordism” National Revolution, this article examines the prevailing idea exchange and political collaboration between Chen Jiongming, the Cantonese military strongman, and the May Fourth intellectual within and beyond regional borders. Between 1919 and 1922, Chen Jiongming not only fostered his anarcho-federalist blueprint, but also garnered support from prominent thinkers hailing from across different ideological camps such as Liang Bingxian, Chen Duxiu, and Hu Shi. Focusing on the ideological and intellectual aspects of warlord rule, this article attempts to situate the study of warlordism against the backdrop of the Chinese enlightenment, to downplay the differences between the man of guns and the man of letters, and thereby to redefine, re-characterize, and reappraise “warlords” as active agents—the initiators—of China's renewals during this formative period.