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But it’s not just the Cubans who’ve left who speak like this. If one ever needs affirmation that this emotion’s targets aren’t limited solely to the past—that one can also be nostalgic for the present and for the future, or simply for life while you’re alive—Cuba is the place to learn. Perhaps Columbus sensed a love for superlatives, by means of some mysterious Genoese intuition, in this island’s very soil. Whatever the source, his first effusive appraisal clocked the abiding tone of much conversation in a country that remains in love with over-the-top endearments, and with diminutive ones, too. Here where the woman at the lunch counter will address you as “mi vida” (my life’s devotion), and apologize for running out of cheese sandwiches by sighing, “Disculpe, mi amor” (I’m sorry, my love), every Pedro’s a Pedrito and every Ana an Anita. Here where every drama contains hints of melodrama, the unbearable—the too much or too little; the too beautiful, the too painful, the too sweet—is to be cherished too, at least in its retelling. There’s a reason Cuba is the home of the bolero: one of many Cuban song forms to conquer the Americas in the twentieth century, it’s a form of ballad devoted not merely to rending the heart but to making it bleed, as well. And it fits. Whether you’re from here, or were from here once, or would like to be again. The island as obsession, the island as wound—it’s a not-uncommon way, for all those who touch Cuba, to engage it.

      Meyer Lansky was once asked why he remained fixated on Cuba during the decades between his first visit here, in the 1920s, and when he opened the Riviera in 1957. He replied with a gangster’s concision: “I couldn’t get that little island off my mind.”2 Neither has any Cuban who’s ever been here and then left, or has parents who’ve done the same. With its balmy breezes and sherbet sunsets and tres leches ice cream and rumba to kill, there’s a lot for which to build affection, and upon which to base one’s own understanding—whether personal or received—of what’s known here as cubanidad: Cuban-ness. Only people from nations with a healthy sum of self-regard see fit to devote blood and thought to the idea not merely that they possess an ineffable nation-ness, but that their country’s essence has contours that are discoverable—and that those contours’ essence is something for which one can, and maybe should, really suffer. But Cuba is one of those nations: it’s not just the intellectuals who stake hopes and careers, here, on arguing about the meaning and contents of cubanidad.

      Of course, part of Cuba’s outsized self-regard, pace Meyer Lansky, is that it’s not a little island at all: at fully eight hundred miles from tip to tail, it’s huge. Its claims to kingliness are based firstly on amplitude. But being the greatest of the Greater Antilles does not a major player in world power make. This big island is also a small country that wants to be a macho-sized nation. That desire—linked always to the aim of not having its big, looming neighbor flick it about—has molded Cuba’s story from Jefferson’s age through the Castros’. And it has led, at moments like the crisis that ensued after Khrushchev sent his missiles, to some tricky spots. Tricky spots will happen, as Quixote learned, when tilting at windmills or superpowers.

      For a brief time in the 1960s and after, and whatever one felt for its bearded leaders’ revolution, those barbudos’ egos and aims gave Cuba a seriously macho profile on the world stage. In an era when dozens of ex-colonial states joined the United Nations, but also in the context of the Cold War whose contending powers forced them to choose sides, Castro’s Cuba became a chief source of inspiration, if not of actual power, for the quixotic dreams of the Nonaligned Third World. That era and Cuba’s role in it were bound to be short-lived. But if politics are momentary, culture is forever. And Cuba’s self-regard, like Cubans’ general pride in their cubanidad, has never derived as much from its politicians’ rhetoric as from daily life—from the cultural fruits and quirks of quotidian streets whose collective ethos, wrote their first determined scholarly excavator, Fernando Ortiz, has always been “creative, dynamic, and social.”3 And from their justified pride, too, in cubanidad’s impacts not merely on their own lives but on others’ lives, too, in the audible impress that its rhythms have long had on the soundscape of the wider world.

      For far beyond the sunsets and ice cream and royal palms, the inevitable core of cubanidad has been this: how it sounds. And it’s been this, too: how its sounds have spread. Long before an aging LA guitarist met Ibrahim Ferrer and heard about a defunct social club in the Havana suburb of Buena Vista, it was here in Cuba’s capital that a series of dynamic idioms and patterns took root and were then shipped, north and south and east and west, to vibrate the globe. In Cuba, this was thanks as well to down-island Afro tributaries in places like Matanzas and Santiago de Cuba, the southeastern seat of island soul. But from the “Spanish tinge” that made the syncopation of New Orleans jazz, to the “clave” rhythmic core of salsa, from Caracas to Manhattan, to the cha-cha-cha figure upon which “Louie, Louie” and other early rock ’n’ roll was built—it was here in the Antilles’ great beachhead, the meeting ground for the lifeways of Congo and Yoruba-land and Andalucía, that the sounds of “Latin America,” and of the Afro-Americas at large, took perhaps their most potent shape.

      For well over two centuries, beginning in the mid-1500s, it was here in Havana that the great treasure fleet of Spain gathered to transport gold and silver from Mexico and from Potosí back across the Atlantic to Seville. Cuba’s role in Spain’s empire was fixed less as a center of production than as the key way station and gathering point for the New World’s riches. It was inscribed in Madrid’s empire, and the larger Atlantic world that empire helped create, as a great port, rich in the kinds of interchange upon which culture’s evolution thrives—and whose riches in that regard only increased after Havana was opened to traders from all nations in 1790. For it was in the decades after that event, as free trade first brought an abundance of African slaves here, and then later saw them freed, that Havana also became the great metropolis of manumitted blacks who rolled their drums and families into Cuba’s capital from its fields to give Havana its lasting stature as the great Caribbean city.

      And the great Caribbean city, make no mistake, is what it remains. Because what you learn, over repeated visits and in absorbing its history, is this: if in 1820 Havana was the most intriguing and beautiful and rhythmic city in the New World, which is to say in the world, it was also those things in 1920—and it remains so, beneath the crust of decay and of politics, as we near 2020, as well.

      Havana, like the island it incarnates, will break your heart.

      * * *

      IT DID MINE, from the moment I alighted here for my first unhurried stay. I was twenty-two and had just sprung from a college apartment with a Che photo on the wall and a worn CD of Cachao’s Descargas on the hi-fi, but with just one previous visit to Cuba under my belt. I’d come down, during college, in one of the few legal ways one then could: with a delegation led by lefty Jesuits who were sympathetic to Cuba’s ruling party because they were lefties but kosher to the U.S. because they were Christian. Our officially sanctioned itinerary, organized by our very nomenclatura Cuban hosts, included visits to places like a model psychiatric hospital with a sign over its playing field, out front, that read “Sports: For a Healthy Mind,” and a little museum area, as we entered, on whose walls were hung big photos depicting “the era of capitalist psychiatry”—people chained to beds, abused kids, lobotomized patients, that sort of thing. This exhibition led onto the gracious grounds of a place where the mentally compromised, treated not with capitalist brutalism but with socialist care, were encouraged to paint pictures and to dance ballet and to belong to bands like the rock ensemble, with its earnest savant belting off-key opera out front, whom we watched to affirm with our applause these good works, anyway, of Cuban communism. This appealing place, our humorless guide intoned to drive the point home, had all been made possible by the revolution—that mythic event, in 1959, that had occurred in the past but was also still going on in a country where every neighborhood still had a Committee for the Defense of the Revolution. Near the Museum of the Revolution, which Fidel’s government built into the old dictator’s palace to commemorate this triumph, a big sign proclaimed, “We Have and We Will Have Revolution.”

      But that was then. And this, now, was me returning to Havana for a year’s stay aimed not at touring the revolution’s official showpieces but at living its daily life. I’d won a fellowship to study language

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