This article provides a historical contextualization of Corporate Social Responsibility (CSR) and its political role. CSR, we propose, is one form of business–society interactions reflecting a unique ideological framing. To make that argument, we compare contemporary CSR with two historical ideal-types. We explore in turn paternalism in nineteenth century Europe and managerial trusteeship in early twentieth century US. We outline how the political responsibilities of business were constructed, negotiated, and practiced in both cases. This historical contextualization shows that the frontier between economy and polity has always been blurry and shifting and that firms have played a political role for a very long time. It also allows us to show how the nature, extent, and impact of that political role changed through history and co-evolved in particular with shifts in dominant ideologies. Globalization, in that context, is not the driver of the political role of the firm but a moderating phenomenon contributing significantly to the dynamics of this shift. The comparison between paternalism, trusteeship, and contemporary CSR points to what can be seen as functional equivalents—alternative patterns of business–society interactions that each correspond, historically, to unique and distinct ideological frames. We conclude by drawing implications for future theorizing on (political) CSR and stakeholder democracy.