Political strategies of external support to democratization are contrasted and critically examined in respect of the United States and European Union. The analysis begins by defining its terms of reference and addresses the question of what it means to have a strategy. The account briefly notes the goals lying behind democratization support and their relationship with the wider foreign policy process, before considering what a successful strategy would look like and how that relates to the selection of candidates. The literature's attempts to identify strategy and its recommendations for better strategies are compared and assessed. Overall, the article argues that the question of political strategies of external support for democratization raises several distinct but related issues including the who?, what?, why?, and how? On one level, strategic choices can be expected to echo the comparative advantage of the “supporter.” On a different level, the strategies cannot be divorced from the larger foreign policy framework. While it is correct to say that any sound strategy for support should be grounded in a theoretical understanding of democratization, the literature on strategies reveals something even more fundamental: divergent views about the nature of politics itself. The recommendations there certainly pinpoint weaknesses in the actual strategies of the United States and Europe but they have their own limitations too. In particular, in a world of increasing multi-level governance strategies for supporting democratization should go beyond preoccupation with just an “outside-in” approach.