In the Millennium Development Goals discussion, the question of how we eliminate bad institutions that perpetuate global poverty often arises. Democracy and participatory institutions are proposed as meta-institutions that are meant to create better ones. Democracies, however, also stumble. We study two episodes of crisis of presidential legitimacy in the Philippines: one arising from perceived electoral failure and the other from involvement in an illegal numbers game called Jueteng. A crisis of legitimacy can arise because the “declared winner” may not be the “true winner” because of the compromise of mechanisms of recall and accountability, or because the “true winner” reveals himself or herself ex post to be the “incorrect choice,” or both. The ensuing crisis of legitimacy, in turn, robs the executive of political mandate and momentum for reform. In the struggle to survive, executive autonomy is traded away as the power brokers of the status quo are enlisted for the defense. Thus, democracy's march to good institutions may be blocked or even reversed.