Recent studies of democratization generally emphasize the role of elites and political pacts in transitions to democracy. They usually give little attention to the institutional conditions for elite's successful pact making. This article argues that although choices by elites are important, pact making does require certain institutional conditions. By examining the democratization experiences of Spain, Brazil, the Soviet Union, and China in 1989, this article argues that only some types of authoritarian regimes have the historical possibility of following a pacted transition. Specifically, the author argues that corporatist regimes have unique advantages in following such a path. On the other hand, the totalitarian institutional legacies of once-entrenched communist regimes left democratic oppositions as broadly based social movements and their leaders with strong populist tendencies. These, the author argues, create structural obstacles to democratization through elite's pactmaking for these regimes.