This chapter discusses Caribbean antifascism’s roots and its connection to the Comintern’s regional radical network, tracing the evolution of the movement from its anti-imperialist origins as early as 1924. The discussion provides specific examples as to how visions of fascism and antifascism were created for and/or adapted to the local and regional realities through an anti-imperialist prism. The study also maps the transnational and transatlantic journey of an antifascist discursive formula from its origins as a Caribbean hologram equating fascism with imperialism, to its official incorporation to the Communist internationalist lexicon as Comintern policy in 1935, and finally to its application as a propaganda formula during the Spanish Civil War. In the long run, while Caribbean antifascism’s anti-imperialist sensibilities may have been lost in translation in the mayhem of theoretical battles and iron-fist, Stalinist policies, the gist of the messages survived the turmoil, and perhaps still lingers on in our culture even to this day.