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Politically charged claims about both "capitalism" and "risk" became increasingly insistent in the late twentieth century. The end of the post-World War II boom in the 1970s and the subsequent breakup of the Soviet Union inspired fervent new commitments to capitalist ideas and institutions. At the same time structural changes in the American economy and expanded industrial development across the globe generated sharpening anxieties about the risks that those changes entailed. One result was an outpouring of roseate claims about capitalism and its ability to control those risks, including the use of new techniques of "risk management" to tame financial uncertainties and guarantee stability and prosperity. Despite assurances, however, recent decades have shown many of those claims to be overblown, if not misleading or entirely ill-founded. Thus, the time seems ripe to review some of our most basic economic ideas and, in doing so, reflect on what we might learn from past centuries about the nature of both "capitalism" and "risk," the relationship between the two, and their interactions and consequences in contemporary America.