This essay examines the meaning, function, and possible future(s) of entrepreneurship in Cuba. Within the larger process of Raúl Castro's unprecedented economic reforms and in the midst of an ongoing “normalization” of relations between Cuba and the United States, we ask: How is entrepreneurship being reconfigured both from above and from within? What effects will that reconfiguration have in shaping the popular response to the simplistic either-or model of a mere “updating” of socialism, on the one hand, versus an implicit “transition” to capitalism on the other? What was—and is—the meaning of entrepreneurship in the Cuban context, especially from the perspective of entrepreneurs themselves? To address these questions, we focus on a particular site: Havana's private, home-based restaurants, known popularly as paladares in Cuba¹. Paladares are the most widespread, dynamic, and profitable mode of entrepreneurship in today's Cuba and—we argue—the quintessential experimental space for the articulation of different, competing notions of entrepreneurship. In other words, how do private restaurateurs balance state supervision and regulation with their need for innovation and flexibility especially since the enactment of major entrepreneurial reforms in late-2010? Our focus on entrepreneurship acquires more urgency (and demands deeper analysis) in the rapidly changing context of U.S.-Cuba bilateral relations following the historic thaw initiated on December 17, 2014, culminating in the establishment of diplomatic relations and the opening of embassies on July 20, 2015. Indeed, President Barack Obama's new “empowerment through engagement” policy explicitly targets Cuba's emerging entrepreneurial class as agents of change following Raúl Castro's 2010 liberalizations. Thus, we conclude by addressing how new state policies on each side are impacting Cuban entrepreneurs and how entrepreneurs themselves are strategically taking advantage of their role as economic protagonists in a new Cuba.

Except in cases where we discuss paladares whose travails have been covered in the media—“El Hurón Azul” and “El Cabildo”—all other names have been altered. Translations from the Spanish are our own. Henken carried out ethnographic interviews with nearly two-dozen paladar proprietors on multiple visits to Cuba between July 2000 and April 2011. Henken's ethnographic work was augmented by that done between 2010 and 2014 by Vignoli.