History's verdict on Zhou Fohai is that he was an arch-collaborator, the éminence grise of Wang Jingwei's government. Yet Zhou's political career in the 1930s as a member of Chiang Kai-shek's factional network did not suggest his later activities as a highly placed collaborator. Prior to 1938, Zhou had little or no political connections to Wang Jingwei; indeed, prior to the outbreak of war he regarded Wang and his followers as bitter factional enemies. Zhou's background, therefore, underscores the complexity and indeed contingency of collaboration in the Sino- Japanese War. This article examines three areas of Zhou's activities in the Guomindang Party-State during the first six months of the Sino-Japanese War: his role as a Chiang Kai-shek loyalist helping to craft key policies; his involvement with developing the United Front after the Lushan Conference; and his part in efforts to seek a negotiated peace with the aim of preserving as much of China's sovereignty as possible. The article argues that these peace efforts were not in themselves a harbinger of collaboration, but were in fact conducted within the framework of the Party-State and involved a variety of leading figures. Despite Zhou's liaison with the communist representatives, he remained staunchly anticommunist and suspicious of their ultimate ambitions, a suspicion that only deepened with the Guomindang's every military reverse. And in his efforts to effect peace negotiations, he faced insurmountable obstacles in Chiang's decision to pursue the military option, in the failure of international mediation by the leading Western powers, and in Japan's ratcheting up its demands as its army went from victory to victory. By early 1938, therefore, Zhou was profoundly pessimistic about China's prospects in its war with Japan.