Chapter 9 examines the evolution of US cities’ relations with Taiwan in the early stages of the ROC’s democratization. It argues that economic interests ostensibly prompted US municipal leaders to establish partnerships with Taiwan. ROC authorities, for their part, made promises of economic benefits to those municipalities that inked sister-city agreements with Taiwanese counterparts and opened trade offices in Taipei. The fact that most cities did not benefit economically from their relations with Taiwan led some local officials and residents to question the pursuit of global markets, but it did not necessarily undermine local executives’ determination to capitalize on the rise of the Pacific Century. The chapter analyses the case studies of trade offices established by Tucson, San Francisco and Atlanta. It concludes by analysing the impact of Taiwanese democratization on US-ROC city-to-city relations, paying particular attention to city diplomacy pursued by Taipei Mayor Chen Shui-bian of the Democratic Progressive Party.