This essay analyzes the figure of the “smoking habanera”—a term I use to describe the sexualized image of a black Cuban woman smoking a cigar, usually wearing a headdress and revealing clothing, whose latest iteration is found among the plethora of small clay figurines on sale for tourists in Havana's street markets. The essay traces the figure to nineteenth-century artist Víctor Patrício Landaluze, whose widely circulated lithographs enacted key modes of understanding race and emergent nationalism in mid- to late-nineteenth-century Cuba. His portraits of mulatas and black women sought to naturalize the stark racial categories by which Cuba then lived, even as the images illuminated the realities of—and white anxieties about—interracial sex and its primary cultural and biological product: mestizaje. I link this historical backdrop to “her” return in the present day, after a hiatus during the early decades of the revolution. The smoking habanera is, I argue, a signature of Cuba's so-called “Special Period,” a figure that interrupts and corrects the exceptionalist narrative of the Revolution and one that assures us that the racial past is not over; in the new economy, the framing and commodification of black women, in answer to new fears and new racial fantasies, takes new and virulent form.