Anarchists who supported the Cuban War for Independence in the 1890s launched a transnational network linking radical leftists from their revolutionary hub in Havana, Cuba to South Florida, Puerto Rico, Panama, the Panama Canal Zone, and beyond. Over three decades, anarchists migrated around the Caribbean and back and forth to the US, printed fiction and poetry promoting their projects, transferred money and information across political borders for a variety of causes, and attacked (verbally and physically) the expansion of US imperialism in the ‘American Mediterranean’. In response, US security officials forged their own transnational anti-anarchist campaigns with officials across the Caribbean. In this sweeping new history, Kirwin R. Shaffer brings together research in anarchist politics, transnational networks, radical journalism and migration studies to illustrate how men and women throughout the Caribbean basin and beyond sought to shape a counter-globalization initiative to challenge the emergence of modern capitalism and US foreign policy whilst rejecting nationalist projects and Marxist state socialism.