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For decades the Miami-based Cuban diaspora successfully represented itself globally as a monolithic bloc and influenced US policy vis-à-vis Cuba. Yet the success glosses over the diversity of the Cuban diaspora, not only in Miami, but in the United States more widely, as well as internationally. The first wave of émigrés, who are known as “exiles,” have for decades campaigned for a watertight embargo against Cuba and have on principle refused to visit their homeland. By contrast, more recent Cuban émigrés, who have left the island since the economic crisis of the 1990s and who are less affluent and have less political clout, have forged cross-border transnational links with kin and friends on the island. In this article, building on Mannheim’s thesis about the long-lasting impact that early-life experiences may have, we show that diasporic Cubans who left Cuba with shared experiences and then settled in the United States or Spain adapted similarly, and relate to Cuba in similar ways, and differently from Cubans who emigrated at other points in time with different pre-migration lived experiences. Specifically, we compare and contrast two historically grounded generations in the United States and in Spain in terms of labor market insertion, political incorporation, and linguistic and cultural acculturation in the two host countries. We thereby illustrate the explanatory power of our historically grounded thesis of diasporic generation formations that we elucidated in the Introduction. The article shows how historically grounded pre-migration experiences continue to shape and mold the ways in which immigrants relate to their homeland from abroad, in ways that neither the assimilationist nor the transnational framework can account for. The article then discusses implications of this finding for the conceptualization of “generation” within research on migration more broadly.