The chapter recounts the history of the concept of risk and of early modern insurance practices as they evolved from communal attempts, mainly in Europe between the seventeenth and nineteenth centuries, to discipline and commodify earlier forms of speculation. The processes eventually involved in risk assessment, pooling, and diversification were neither inevitable nor entirely capricious. They were complicated and indeterminate, and accommodating structures of government developed in tandem. The chapter also provides an orientation to increasingly complicated scholarship focused on the governance of risk and uncertainty as considerations of their consequences migrate over time and geographic space. It notes how leading business firms around the world, not just in the insurance industry, came to base their strategies on sophisticated models that take for granted commonplace, and even simplistic, notions of risk. Those models are dynamic and they now shape larger structures within which firms and people interact. As collective impressions of risk become more complex, shared sources of uncertainty also rise, often because economic and political systems are misaligned.