Straits of Fate: A Young Cuban-American Visits the Homeland

The sign, an example of Cuban government sloganeering, reads, "Cradle and Tombstone of Distinguished Patriots."
The sign, an example of Cuban government sloganeering, reads, "Cradle and Tombstone of Distinguished Patriots."
Photo by Humberto Guida

José Martí International Airport in Havana appears much as it did in the early 1960s. Large Casablanca fans, peeling paint, vinyl tiles, and faded plastic poster boards direct the flow of visitors to customs. The only sign of modernity to greet arrivals in the international terminal is a large billboard promoting medical tourism. It pictures an attractive middle-aged blonde on a gleaming Cuban beach, her arms outstretched, basking in tropical serenity — it looks like an ad for a feminine hygiene product.

"Cuba, un destino de salud para todos," it reads. "The health destination for everyone."

When I arrived in Havana this past June, the first Cubans I encountered were relaxed but neither smiling nor overly polite. As I passed through customs, I was nervous about handing them my American passport. But the young customs agent didn't react. He merely asked that I look up at the small camera over his head for a photo. Then he handed me my passport, unstamped.

As I made my way to the main escalator, I heard the uniformed airport staff speaking in the Cuban accent I'd grown up with; many of them had distinctly Caribbean mulatto features. They walked on their heels. They sank into their hips. I recognized these people.

I made my way past the gate and into a general receiving area. That's where I saw a familiar face. I had never really bothered to look at the pictures of my second cousin Lara, my maternal grandmother's niece. But I didn't have to. I knew those eyes, the way she tilted her head to the side, the composure obvious in her lips. She looked just like my abuela Coralia. I didn't even look down at the sign she had made with my name on it.

"¡Hola, prima!" I hollered. We hugged.

It's a hell of a thing to meet your family for the first time as an adult and to see your eyes in theirs. I felt a connection to this island instantaneously, and I hadn't even walked out of the terminal into that hot, humid, so-heavy-it-hugs-you air. She was accompanied by her husband Juan, who was tall, tan, and wearing a button-up shirt tucked into his pants despite the searing heat. A cigarette pack protruded from his breast pocket.

We got into their car, a mid-'90s Eastern European make, similar to a Toyota Tercel, with a stick shift. Juan said he was proud and lucky to have it as I nestled into the back seat and we left the airport for the city. All I could think was, Holy shit! I'm in Cuba.

I was born and raised in la saguesera — Southwest Miami-Dade, where Cubans congregate in a very visible (and loud) majority. I'm a second-generation Cuban-American who seldom felt like an outsider as Latinos in many other parts of this country do because, well, it's Miami.

Let's get something straight. Los Angeles, New York, and several other large American cities have vibrant, influential Latino populations. But Miami represents the most significant example of a major U.S. metropolis undoubtedly and unapologetically run by Latinos, with Cubans being the force at the helm. We remind ourselves of that fact every day between shots of Cuban coffee and pastelitos de guayaba. And we will tell this to anyone who comes within earshot.

Today, Cuba is undergoing change. It's not the overnight political transformation my Cuban-American exile community craves, but a slow-moving economic and cultural metamorphosis that rides the wave of the rest of the world.

In the past couple of years, I developed a feeling that the time had come to stop hearing and reading about those changes and go see them for myself. That feeling was spurred by years of questions from many of my non-Cuban friends about whether I'd been to the island. I grew tired of explaining the politics of why I was depriving myself of the experience despite the island's proximity. I grew jealous of Mexican, European, and Canadian friends returning from the trips of their lives, sliding through smartphone photos of my family's homeland — a place I had never seen in person. Half the time, it felt as if they were rubbing it in my face. I began to think I was ignoring my heritage. I was staying home because of other people's feelings.

The world my family left behind has been a theme in my life, as it has been in the lives of many other second-generation Cuban-Americans. Events that led to my very existence are rooted on an island just over the horizon from where I was raised. Until I landed that day in Havana, those events lived only in my imagination. That steamy, pulsating, fabled place has haunted me since I was old enough to understand my family was from somewhere else.

Now I would become the first of my clan to return to Cuba. "Return" is, of course, a relative term because I had never been to the 780-mile-long island. But it would feel like a return to me.

My great-grandfather on my dad's side went to sleep one night the owner and operator of a dairy farm in Manzanillo. He woke up the next morning, headed to the farm, and found the gates locked. His employees, who were waiting outside, were perplexed. Authorities had left behind a letter indicating which regional office he'd have to visit to complete the government's appropriation of his life and his dreams.

"¡Viva la revolución!" an official yelled as he drove off in a topless military jeep. Fucker.

Following Fidel Castro's 1959 victory, my mother's family quickly packed as much of their lives as they could fit into a suitcase. They gathered what little cash they were allowed to withdraw from the bank by begging lifelong friends who worked there to help. Then they grabbed the last few seats on one of the last few planes departing the country. They left behind everything and everyone they knew.

My maternal grandfather, Eduardo Dieppa, returned in April 1961 as part of the CIA-backed Bay of Pigs invasion. He hoped to spark a counterrevolution. At age 39, he was one of the oldest members of the Brigade 2506 and a radio operator for his unit. He was captured and spent a year and a half as a political prisoner in Castro's jails. His captors brutally beat him in the midsection with the butts of their rifles — literally busting his guts.

Abuelo Eduardo survived until his release was negotiated by the U.S. State Department. He rejoined his wife and kids in Miami. My maternal grandmother, Coralia, a devout Catholic, strait-laced and traditional, had been taking care of five kids on her own in a country where she did not speak the language. She was happy to see him despite how skinny and frail he had become. And though injuries from the beatings had forced a surgeon to remove a quarter of my grandfather's intestines, he joined the other brigadistas to walk in a parade that finished inside the Orange Bowl, where John F. Kennedy welcomed the unsuccessful counterrevolutionaries as "patriots and heroes." (The Democratic president had reneged on previously promised air support just before the invasion, which eventually pushed Cuban-Americans to the Republican Party.)

In those years, many around the world admired Fidel, his brother Raúl, and their proto-hipster Argentine buddy, Che Guevara. It seemed these iconic leaders had overthrown the deeply corrupt regime of right-wing dictator Fulgencio Batista and replaced it with a democratic government.

But then Castro declared publicly that he was a devout Marxist and that the revolution was Communist. Cuba became a one-party, totalitarian dictatorship. For many on the island, it took a few more years to realize the "oops" factor of these events. Not until their homes and businesses were forcefully nationalized and redistributed did many know they'd been duped.

My father's relatives were initially sympathizers, but they left in the late '60s after the street-side assassination of my paternal grandfather's best friend, the revolution's chief physician, Manuel "Piti" Fajardo. He had refused to participate in the witch hunts and firing-squad executions of political dissidents.

My paternal grandmother, Maria Dolores, who was sassy, loud, and tough, remembers her last conversation with Fajardo. It took place in the living room of their upscale apartment in a Havana suburb. He told her: "Maria, this revolution is turning red," referring to the impending Communist takeover. The insinuation was that they should look into leaving Cuba. So she secured exit visas for her and her kids to Mexico City. My grandfather Humberto, whose name I bear, and two of his friends were doctors, thus prohibited from leaving the country. So they spent 36 hours swimming to the American naval base at Guantánamo Bay, their faces smeared with camouflaging black shoe polish. They were dehydrated and half-dead when they saw an American military boat with the Stars and Stripes on the bow.

On my trip, if there was any indication of how Cubans of my parents' generation who stayed feel about the revolution today, it didn't come from any spoken words. It was a look in older Cubans' eyes that cut through their big egos. It expressed what their mouths would not say: "We fucked up."

This is most evident in Havana Vieja (Old Havana), a five-century-old city where the ghosts of a glorious past pace among the old buildings, some of them restored and picturesque, others crumbling and decaying, but all equally haunting. And there are always reminders of the revolution. Cubans shout about everything, but they whisper when talking about the government. There are no ads on billboards, only government propaganda and motivational messages on the public walls.

For those who don't understand the specific lament of Cuban exiles, keep this in mind: Cubans pre-Castro didn't live in a Third-World situation. Sure, the island was corrupt, but there was an ample and proud middle class. There was opportunity and economic progress. For much of the '40s and '50s, the island's gross domestic product ranked third in the Western Hemisphere, trailing only the United States and Canada.

So these older exiles saw their small but respectable and comparatively prosperous country go to shit in one fell revolutionary swoop. Cuban exiles are a deeply traumatized group. An overwhelming feeling of loss abounds. And it's that trauma that prompts the vast majority of them to refuse to go back to Cuba as long as the Castro dictatorship is still in power.

I went back for them.

Beautiful beaches and Jurassic-looking landscapes are just part of the attraction for young Cuban-Americans.
Beautiful beaches and Jurassic-looking landscapes are just part of the attraction for young Cuban-Americans.
Photos by Humberto Guida

After leaving the airport that steamy day in June, Lara, her husband Juan, and I head along the lush eastern bank of the Río Almendares to Nuevo Vedado, a neighborhood just west of Havana's city center. Then we cut onto side streets to my cousin's home. The neighborhood reminds me of a rundown version of Miami Beach, like the South of Fifth neighborhood in the mid-'80s. Art deco buildings line pothole-riddled streets. Along the way, Juan lets me know that with all the tourists coming, "They're going to get to fixing these streets, but no matter, we get around."

Their well-kept six-unit apartment building is for the most part as nice as the condo I lived in between Jefferson and Meridian Avenues a few years ago. Located in a quiet, quaint neighborhood, their building is freshly painted pink. Kids chase after one another in the street. Pedestrians wave to my cousins as we arrive.

Lara explains she has turned part of their place into a one-bedroom casa particular, basically a room for rent. It has an air conditioner, its own bathroom, and a private, gated entrance. To remodel it, she used whatever savings she had, along with cash donations from family members.

After showing me their home, Lara, Juan, and I walk a block to a private restaurant, a paladar, called La Rosa Negra. There are just four tables and a full bar. On the menu are authentic Cuban meals just like you'd see in Miami: pork chunks in a garlic broth with fried plantains, plus the ubiquitous black beans and white rice.

There is an immediate intimacy. To me, Lara represents a part of my family I never knew. To her, I am a new future she is finally getting a chance to understand. Lara says she is at the heart of the tourism-fueled change happening in Cuba. It is a portal to an outside world and outside people.

"We host people from all over the world in our home," she says, "Germans, Canadians, Chinese. We are excited. We see opportunity. We love having people visit so they can see how special Cuba is."

Her father Pedro, my great-uncle, was the only member of either side of my family who stayed. He was a strident supporter of Castro's revolution. When my grandmother left, he saw it as abandonment. When her husband, his brother-in-law, my grandfather, returned two years later as part of the Bay of Pigs invasion, Pedro saw it as betrayal.

Yet here we are, having spent our lives on opposite sides of the revolution. Though we just met an hour earlier, we're eating together in Havana. What would the old men, now deceased, have thought?

"My father loved your abuelita very much," Lara explains. "He would be so happy to know that this side of the family would return one day to reunite."

Lara's husband Juan is a civil engineer, every bit as gracious and chatty as any Cuban you might find at the ventanita of a Cuban bakery on Calle Ocho. He, more than many others, holds onto the dream of the revolution. In his 50s, he is a product of its system. A highly educated man with an advanced degree in civil engineering, he's curious about my gadgets — a camera, a smartphone, and a laptop.

There's also a certain defensiveness. You can tell he's a very proud man. Like a lot of Cubans, he wears that pride on his sleeve no matter how things are going. "This is a country that loves its people," he tells me. "And we are happy. We are not subjected to the rat race like in the U.S. But we still eat good." Then he asks, "How is your food?"

Truth be told, the food in Cuba was better than I imagined. It compared well to the menus at Miami staples such as La Carreta. Though if you're a vegan or health-food nut, all I can do is wish you luck in Cuba.

While Lara stays away from political talk, Juan continually reminds that the state of the island is better than what we hear across the Florida Straits. "Look at how good we're eating," he says between sips of Cristal, one of two state-owned beer brands. "Let people back in Miami know we're doing good. Let them know we're not starving." But the truth is a meal like this one is a luxury my relatives enjoy infrequently.

Juan also offers a message to the impending onslaught of Americans expected to arrive in the coming year: "They can suggest new things, but you shouldn't go into someone else's home and tell them how to paint their walls."

A couple of hours later, Juan confides that he is worried about his son Juan Jr., who is working and going to school in Mexico. The dog-eat-dog capitalistic world might erode some of the 27-year-old's core socialist values. But because Juan Jr. is married with a daughter, he explains, the young man is in no position to let political thinking interfere with his family.

"It hurts a little because he can stay here, build here in a place that has given him so much support," Juan says, "but he's working in Mexico. I hope as things get better here, he might come back to work in his home country."

Juan is optimistic about the opportunities that lie ahead. While the casa particular is owned and run by his wife, he's all about online marketing, the booking website, and social media. He just needs better Wi-Fi (which Cubans pronounce weefee) because internet access is intentionally slowed and regulated by the state.

Juan also hopes to one day form his own cooperativa, a private construction company, which the Cuban government is slowly allowing groups of engineers to form. But it must employ no less than seven or eight engineers, he explains. It takes that many to ensure no one person gets too close to being well-off. It has to be a "collective" thing, he says.

The next day, we head to the Playa del Este, a beautiful municipal beach where locals are allowed, unlike the popular tourist-only destination Playa Azul, 30 minutes east of here in Varadero. Sitting on the edge of the unbelievably blue, clear-as-glass sea water, Juan tells me more about his dream of starting a business. He draws in the sand with a twig while he talks. Unlike the rest of his conversations, which are close and face-to-face, his description shows a profound longing.

"I have to find the right associates," he explains. "All need to be in good standing. The business plan gets reviewed by the regional office. You still have to wait for licenses because they already cut off the number going out this year." He goes on and on. The red tape is dizzying.

After that, he challenges me to a swimming race. He swears he'll beat me to a nearby buoy. I'm not a competitive swimmer, but I'm also not about to back down from a physical challenge by a guy 20 years older. After all, I'm also a hot-blooded Cuban, and this trip only serves as a validation of my nature. We hit the water. I beat him by 20 yards.

"My shorts came undone during the race!" he hollers, laughing at his own excuse. I love this guy.

Back in Nuevo Vedado, I notice every other house in this neighborhood is either a casa particular, as evidenced by the Airbnb and Trip Advisor stickers on the windows, or a paladar. Many taxis are private too.

One day, I hire a personal taxi driver for $70 from dawn to dusk. Piloto is a clean-shaven, well-dressed mulatto in his 30s. He rents a 1950s Lincoln Continental in exchange for a percentage of his earnings. The car is vintage, original body, but everything else is jerry-rigged. The leather is patched up. The clutch is from a Russian car. The brakes go out a few times while taking turns. And the smell of unleaded fumes gets me high. But it runs like a dream.

Like so many Cubans here, Piloto has a PhD in engineering. Cubans are some of the most educated people on the planet. Half the population goes to school for, like, forever. What else is there to do? But for many, a great education is not enough. With his taxi, Piloto earns more in one day as a driver than he does for an entire week as an engineer for the state.

"I have three kids, a wife, and I hope to start a construction firm soon," he says. "But for now, driving is the best option. Tourism, the cruises, it's changing things." As a taxi driver, Piloto says, he also gains access to hotels, shops, and restaurants designated for tourists and generally off-limits to Cubans. He asks me about Miami and the United States. He's trying to get an edge on what is to come. He wants to be ready for when the wave crashes.

It's more difficult for a Cuban to get hold of free-market ideas than the typical Westerner because the media, education, and access to the internet are so restricted. But thanks to tourists, Cubans are being peppered with living, walking, talking, interacting human beings who can speak to what really goes on in the developed world. It is these conversations, even more than high-speed web access, that are enlightening the Cuban people to other possibilities.

"Now we have gotten to the point where we are wondering maybe you can have more than one political party," Piloto tells me as we pass sign after sign with revolutionary iconography of Fidel and Che. "Why can't we do more for ourselves?"

"Now you're talking," I say from the back seat.

Humberto Guida
Humberto Guida
Courtesy of Humberto Guida

A large hipster society rules the nightlife and art scenes in Havana. The two intersect in a perfectly presented venue on Calle 26 called Fábrica del Arte Cubano. One night toward the end of my stay, I meet Juan Jr. and his wife, who have recently arrived from Mexico. In their mid-20s, they are game for taking me out to Fábrica. Outside, it is not unlike a velvet-rope-guarded South Beach hot spot. The venue is part of an expansive complex that includes a boutique, a concert hall, an art gallery, and a gourmet food court.

I hang out with my cousins and drink Havana Club and Coke (which I don't order as a "Cuba Libre"). In the food court, I enjoy Wynwood-food-truck-quality bocaditos. Then we move into the main room at Fábrica and take in the sounds of Alex Arias, a world-renowned Havana-native singer-songwriter. In between, we check out some of the most provocative, original, captivating art I've seen this side of gallery parties in places like Wynwood, Venice Beach, and SoHo.

We return the next night to have dinner at El Cocinero, a rustic eatery next door to Fábrica where President Obama ate during his visit. Located in a remodeled, century-old, abandoned red-brick factory between Vedado and Miramar, it is located up a winding staircase on a rooftop overlooking downtown Havana. There is a posh central bar and a chic vibe. I enjoy a fusion of food cultures amid a nouveau-urban menu. I have to remind myself that this is, in fact, Havana and not Chelsea. This might not be the Cuba of the golden era, but it's not the Cold War either.

There's an eager joy that simmers in the youth of Cuba as they congregate by the thousands on the Malecón while shimmering and shaking their butts to the battling conga drumbeats and radios. Change is definitely happening. I see it in my hopeful relatives and the optimistic friends I meet along the way. The surging tourism in Cuba has led to all of this optimism. So has the privatization of other sectors of the economy. So I believe there's a crack in the wall that will lead to greater liberty.

But still, I have some mixed feelings. Before I embarked on this trip, a good friend from high school laughingly said, "I think I should punch you in the face," after I told him I was going.

I guess I was ready to deal with the resentment from folks at home in Miami. But I'll admit this: After being there and seeing the crumbling, unkept façades of the beautiful country that used to belong to our grandparents, I better understand why they don't go back. I would not recommend that my grandmothers visit Cuba. Not yet. They'd cry and become angry. It wouldn't be pleasant.

My parents' generation, though, should try it. They commonly left as kids. The decay of the country will hurt them, but they're young enough to see the potential future for Cuba, perhaps even take part in it. And much of this generation has succeeded in America. So what darkness they'll feel when they encounter what was left behind will not overshadow the light they'll find among their people in the long-lost place of their birth.

And as for Cuban-Americans born in the United States. Oye, mi gente, enough with the bluster and bravado about not going to Cuba for some high and mighty reason. The stories about everything our families lost are just that to us — stories. This is an idea, not an experience. We didn't lose anything we already had. We weren't there. We do not have the same emotional connection as our grandparents, who surrendered their homes and lives. It's not our trauma. Hell, most of my generation wouldn't have been born if it weren't for the Cuban revolution, because most of our parents met in Miami.

You're not punishing the Cuban government by not going. The rest of the world is already there. You're only punishing yourself. Get off the high horse. Book a flight to Havana, especially because who knows what will become of our diplomatic relations with Cuba now that Donald Trump has been elected president. The Cubans I met really do want to connect with Cuban-Americans. They are ready to greet you and get to know you and learn from you. They are ready for change.


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