In this article, Raudiel F. Peña Barrios examines the wave of democratization that swept through Latin America at the end of the 20th century, highlighting how various autocratic regimes transitioned to democracy in response to pressures for change. The author notes that many of these regimes, which initially legitimized themselves as temporary responses to threats such as communism during the Cold War, eventually accepted negotiated exits from power. This phenomenon reflects a broader trend where the retreat of communism shifted political calculations among military dictatorships in Latin America, allowing for democratic transitions even after periods of intense repression. He further explains that Latin American military dictatorships were often justified as a response to societal pressures linked to the Cuban Revolution and the rise of guerrilla movements across the region. As the necessity to combat communism diminished, these regimes began to acknowledge their untenable positions. The author argues that while the justifications for their authoritarian practices do not excuse the violations of human rights, the unique socio-political contexts of each regime inform why some were more inclined to embrace democracy than others. The implications for Cuba today are significant, as the article suggests that understanding the historical patterns of transition in other Latin American countries may offer insights into the potential for change in Cuba's own political landscape. As Cuba approaches this critical juncture, the reflections on past regimes serve as a reminder of the challenges and possibilities that lie ahead for the island's future governance and civil liberties.