The anticipatory logic of speculation and preemptive politics of risk are increasingly gaining significance in a globalizing neoliberal world. This study traces risk and speculation as aesthetic and political-economic strategies in factual and fictional discourses emerging at the North American Pacific Rim within a decade around 2000. Its exemplary close readings in particular focus on three fictional texts (Kathryn Bigelow's Hollywood film "Strange Days", 1995, Karen T. Yamashita's novel "Tropic of Orange", 1997, and Larissa Lai's novel "Salt Fish Girl", 2002) whose intricate aesthetics pass perceptive critique on concurrent political-economic discourses and their subtle reconfiguration of race, class, and gender. The speculative near-future scenarios projected by these artifacts expose the rise of risk as a new rationality of governance. At the same time they illustrate neoliberal speculation as a new paradigm of subject formation at a hyper-capitalist, millennial Pacific Rim.