This Article, awarded the 2011-12 Liberty Mutual Prize by Boston College Law School, identifies four different conceptions of insurance that have operated in the debates about insurance and insurance law in recent decades, analyzes these conceptions, and examines the normative agendas that drive them. These are the contract, public utility-regulated industry, product, and governance conceptions. Although these conceptions adopt very different perspectives, each is a way of struggling with the two fundamental questions that modern insurance law has continually faced. The first question involves the extent to which the language of an insurance policy should determine its legal effect. This is the insurance law version of the age-old question of the validity of one-sided provisions in contracts of adhesion. Because virtually all insurance policies, including high-end corporate insurance policies, are standard-forms, it is a question at the core, not the periphery, of insurance law. The second question involves the proper influence of what are sometimes called “public law” values on the scope of private insurance coverage. This is a version of the question with which much of modern private law struggles. To what extent should private law be about doing justice between two contracting parties, and to what extent should it also be concerned with other, more nearly public law matters, such as the impact of litigation outcomes on the future behavior of other parties, or equal treatment of similarly-situated policyholders? Ultimately, the Article argues, adopting a particular conception of insurance is no substitute for making or rejecting the normative choices that each conception entails. It is not our concepts, but our political, economic, and social values that underlie and underwrite legal doctrines and practices. Nonetheless, sometimes we do not see through our conceptual structures but instead are led around by them. This is part of what is taking place in the contests among different conceptions of insurance. In such circumstances it takes the kind of critical analysis this Article undertakes in order to expose the normative agendas that are doing the actual work within each conceptual structure