This article addresses how U.S. public diplomacy, in educational, cultural, and media-focused projects, has influenced the development of Venezuela’s civil society and democracy during three eras. First, during the Cold War, to contain communism, U.S. public diplomacy prioritized educational projects targeting Venezuela’s military and youth. As military coups occurred across Latin America, the U.S. government sought to educate and spread information among military officers who could promote anti-communist political development, especially in Venezuela. Second, in the 1990s, U.S. public diplomacy began shaping the development of political structures and democratization in Venezuela by training leaders of political parties, civil society, and media groups. Until the mid-2000s, the United States also sought to influence political parties and elections by establishing non-governmental organizations and interacting with a new generation of politicians. Third, in today’s era of digitalized international relations, U.S. public diplomacy has mobilized digital diplomacy to sway Venezuela’s political development, notably in the 2015 parliamentary elections and 2018–2019 political crisis. Although the United States has cooperated with independent Venezuelan media organizations and broadcast across local social media networks, the 2015 elections and recent political crisis revealed that local media are more popular among Venezuelans than their U.S., European, and Russian counterparts.