Many theories attempt to explain why some countries democratize and others do not. Existing accounts, however, focus almost exclusively on structural factors and ignore individual leaders. In this article, we argue that leaders educated at Western universities are more likely to democratize than other leaders because Western education socializes leaders to prefer democracy and creates transnational linkages that alter the strategic calculus of democratization. Utilizing an original data set on the specific colleges and universities world leaders attended, we show that Western-educated leaders significantly and substantively improve a country’s democratization prospects.