Immediately after coming to power, the Clinton administration declared the consolidation of market and democratic institutions in Russia to be a vital American interest. The administration's central tactic for promoting this outcome was to help Boris Yeltsin remain in power. In a major assault on Clinton's historical legacy, much of the scholarly community maintains that U.S. policy was fundamentally flawed, both morally and strategically. In the view of these analysts, post-Soviet Russia's founding president was an autocratic leader who derailed the country's progress toward democracy. However, this body of research focuses exclusively on the Russian Federation and fails to utilize comparative referents. In contrast, we analyze the experiences of the full population of post-communist states of Eastern Europe and Eurasia from 1991 to the present. Whether examined in cross-national or longitudinal perspective, we find that Russian democracy under Yeltsin was, relatively speaking, a success. We conclude that the Clinton administration's policy of support for Yeltsin both served various American foreign policy interests and strengthened the prospects for democratic consolidation in Russia, thereby fulfilling the dictates of both real- and idealpolitik. In addition, the relative success of Russia's democratization in the 1990s, the reversal of that pattern in this decade, and the magnitude of the transformation of the polity under Putin all demonstrate the pivotal role played by presidential leadership in Russia's transition.