The last time my plane arrived at the airport in Havana on March 20th, 2016, Air Force One had beat me to it by an hour. President Obama was the first sitting US president since Calvin Coolidge to visit the island since 1928. Ben Rhodes–Obama’s deputy national security adviser and his point man on the normalization of relations between the United States and Cuba–noted how unusual it was to watch the president press his face against Air Force One’s window to peer out as the plane touched down, something Obama rarely did.

“We could see the crushing poverty,” Rhodes recalled. “The dilapidated neighborhoods and all the corrugated roofs on the buildings. Obama said two things I remember very well. ‘It reminds me of some of the poorer places I’ve traveled to in Africa… It certainly doesn’t look like much of a threat to the United States either.’ He said it with a kind of biting sarcasm, but not in a humorous way. We had turned this place into a totally impoverished island because they were supposedly a national security threat.”

President Obama had also brought his family for the historic 48-hour tour. The last stop was to watch a baseball game in Havana’s beloved but rickety Estadio Latinoamericano, an inadvertently carbon neutral 55,000-seat stadium without a parking lot. Obama and his family sat alongside Raúl Castro at the game. Castro’s more famous brother Fidel–still hanging on at 89-years-old–had just over eight months to live. Three days after Obama left, the Rolling Stones performed a free concert in Havana for over 500,000 Cubans. It all felt like one of those rare moments Graham Greene once described as “when the door opens and lets the future in.”

Ben Rhodes recalled being with Obama in South Africa three years earlier for Nelson Mandela’s funeral, a man the United States had officially branded a terrorist until 2008, five years after he was awarded the Nobel Peace Prize for his contribution to the peaceful elimination of apartheid.

“We had not yet announced the opening with Cuba,” Rhodes told me. “I said to Obama, ‘You’re gonna be on the dais with Castro. You should really think about what you wanna do.’ Obama said, ‘I’ll shake his hand, of course.’ I told him that’ll be a big story back home, which it was. He said to me, ‘The Cubans have more right to be at this funeral than I do as the American president.’”

“¿Que bolá Cuba?” were Obama’s first words to the Cuban people after arriving. Obama’s use of the Cuban colloquial greeting for “What’s up?” delighted millions.

The world’s media descended on the island. There were reports of “cautious optimism” from the Cuban people. For decades Cubans used to joke that if Spanish lacked a future tense Fidel would be silenced, since all his words were devoted to broken promises. If the campaign of hope message that Obama had used to cast a spell on the American public in 2008 had worn off over the past eight years in the United States, it felt revitalized applied to Cuba.

While the cost of hotels had surged beyond Paris prices for the surreal event, many visitors bitterly complained how the level of service remained frustratingly third-world. As I approached Cuban customs in the airport, Communist inadequate hotel amenities and unmotivated waiters remained low on my list of pressing concerns. I was shitting my pants about getting detained. The crowd bustling to get into Havana was unlike anything I’d ever seen. Predictably dramatic and intense increases in Cuban security were immediately obvious. The last thing in the world the Cuban government wanted to happen was to transform some street corner in Havana into the 21st Century’s Dealey Plaza.

I had legitimate reasons to expect I’d never be allowed back in Cuba. On my last visit five years earlier, I’d illegally filmed what turned out to be the last interview with Teofilo Stevenson, the legendary three-time Cuban Olympic boxing champion, shortly before his death in the summer of 2012. After Fidel, Stevenson had the second most famous face on the island. In the 1970s, he had turned down millions to leave Cuba and fight Muhammad Ali. Even more absurd, he turned down the chance to have been Ali. By the time I caught up with him, he was chain smoking and a severe alcoholic. Stevenson growled, “I’m broke,” and only agreed to speak to me if I secretly paid him $130. When The Miami Herald learned about it they ran a front-page story about the interview as if it were the equivalent of a Michelle Obama sex tape.

So I took some inelegant, telenovela-worthy precautions to assist my odds of getting in. I flew in from a third country, officially a vacationing tourist who made no attempt to secure press credentials. I also entered under a different name and nationality than what the Herald had publicized in their article.

While soldiers and dogs sinisterly paced around the customs room, I scanned the faces of agents for the most sympathetic-looking option and was grimly waved on. Sphincter clenched, I handed over my passport. Suddenly a menacing red box appeared on the custom agent’s archaic computer screen, accompanied by the sound of an old emergency brake yanked on a jalopy. “Here they come,” warned my inner voice. The agent glanced at me and smirked just long enough for my imagination to conjure up the next 36-hours being cavity searched in a Cold War interrogation cell. I froze as she pounded her keyboard a couple of times and the red box evaporated and the alarm magically ceased. “Stubborn machines,” she sighed, handing back my passport back and waving me through. “Bienvenido a Cuba.”

Eight years after the unprecedented impact of Obama’s historic visit, two new jokes floated around Havana speaking to how much has changed: What does a Cuban child dream of becoming when they grow up? A foreigner. What do you call a Cuban orchestra after a world tour? A soloist.

I met my wife 17 days before the first case of Covid-19 was announced in New York. We moved in together during lockdown after four dates. For our first wedding anniversary in October of 2023, I suggested we might visit Havana. Everything I heard about Cuba from people still living there and from journalist friends who had covered the island for years suggested the situation was transforming into something of unprecedented bleakness. And now, a year after our visit to Havana, after a recent four-day nation-wide blackout, severe food, gas, and medicine shortages, with all this hellbroth coming to a boil, the world finally seems to care.

“Oh wow,” Em sarcastically gushed. “For our first wedding anniversary I get to spend a week with my husband’s most complicated ex-girlfriend.”

Nobody had ever framed my relationship to Cuba this way before. It had felt more akin to a one-night stand that lasted 24 years–a melancholy romance with interruptions. Not that America’s relationship with Cuba was any less fraught: five times more dollars were offered to buy Cuba than for Alaska and the Louisiana Purchase put together before basically just taking it over (along with Guam, Puerto Rico, and the Philippines) anyway after the Spanish-American War of 1898 and pimping it out.

“We talked about Cuba on our first date,” Em smiled. “What’s always made me feel insecure about your connection to Cuba is how I’m so completely different from it. There’s no Venn diagram. It’s just hard for me to understand how you can be so connected to it and reconcile the fact you feel connected to me. But let’s meet your ex anyway.”

Em knew about my fears over getting in, but waited until the final descent over the Florida Straits to express some concern.

“Isn’t it distinctly possible that the custom agents have better computers now?” Em sighed. “In which case, are we going to spend our entire anniversary in the Havana airport with me waiting for you to be interrogated until–best case scenario–you’re thrown out of the country?”

I shrugged.

“Actually, I’m not on their blacklist,” Em said cheerfully. “I’ll grab some pina coladas at the Hotel Nacional bar until you’ve been released.”

After stepping off the plane, winding through the blood-red corridors and descending a flight of stairs to enter the immigration hall, my wife turned to me with a baffled expression.

“Where is everybody?” she asked.

Scanning the area, it was one of the most surreal sights I’d ever seen traveling to Cuba since my first trip in 2000. The entire room was empty of any visitors trying to enter. In the wake of Obama’s visit seven years ago, Havana became one of the most Google-searched locations on earth to vacation. Millions of Americans followed him and the airlines couldn’t accommodate the demand. Havana’s airport was scheduled to be expanded and cruise ships were backed up trying to get in.

And now aside from a dozen olive-fatigued customs agents sitting in their booths looking bored but also unnervingly welcoming, virtually the whole labyrinthine apparatus for corralling visitors was as bare as a clothes hanger.

“How is this possible?” Em asked.

The passengers on our flight sailed through immigration with the entire procedure resembling something like lifeguards waving us down a waterslide.

“Any other predictions?” Em asked. “You’re oh-for-one so far.”

Outside baggage claim, the scene was the exact opposite: droves of Cubans sardined in the departures section trying to get out and moist-eyed crowds of friends and family watching close by. Em gestured toward the CADECA money exchange offering the official government exchange rate of 24 Cuban pesos for an American dollar. I’d heard from the friend who was picking us up that the black market exchange rate offered 245 Cuban pesos for a dollar. In a country where the economy had been cut in half since the pandemic began, every Cuban is being crushed. Americans spend more money on lottery tickets than the entire Cuban GDP.

We stepped outside the airport doors into Havana’s muggy, tropical embrace. I have never returned to Cuba without immediately experiencing the aperture adjusting dramatically both on it and also on myself. The city’s perfume climbed into my nostrils, a swirl of salty sea breeze carrying diesel fumes, tobacco commingling with melted chocolate, followed by the contents of a forever-unflushed toilet. Em nudged me, alarmed by the horde of illegal cab drivers hissing violently to get our attention.

I watched her grapple with the disorientation many first-time American visitors to Cuba experience upon arrival: in this alternate reality are you Dorothy in Oz or Alice through the looking glass? Unfortunately, Dorothy’s role is far more complicated and fraught in Cuba’s Oz, because whatever Kansas you come from doubles as almost any Cuban’s overblown fantasy of an American Emerald City. The fantasies you bring to whatever Cuba represents for you collide with the desperate fantasies Cubans entertain about what where you come from represents to them. Unlike the 1939 classic film, in L. Frank Baum’s book The Wonderful Wizard of Oz, visitors to the Emerald City are required to wear green spectacles literally locked onto their heads to ostensibly protect them from going blind from the glare of “brightness and glory.” But the spectacles' actual function is to make sure you don’t realize the Emerald City is far less green in actuality than you’ve been led to believe.

The Alice feeling in Cuba can take its time to take hold. When exactly does a child’s happy relationship to zoos or aquariums start to fray and dismantle into something tragic and cruel? At some point you can’t just look in without paying the price of empathizing with the eyes looking out. Alice’s Adventures in Wonderland are not adventures for anyone but her. The rest of the characters are trapped in an open air prison, performing as extras, until Alice wakes from her dream.

“Why are they hissing like that?” Em asked.

“Because a Cuban brain surgeon makes less in six weeks here than what one of them will make on a fare. Half of them are probably scientists or lawyers.”

Surveying the crowd, I couldn’t spot my friend Ria anywhere.

Em turned to me, “If Ria isn’t coming, should we just go with one of these guys?”

“Give her a second,” I said. “Her car probably broke–”

Suddenly Ria cut through the throng of Cubans jingling the keys to their rusty Soviet-era Ladas. She slapped some silver-streaked curls against her forehead in embarrassment and at 44 still looked exactly like a Cuban Audrey Hepburn circa Breakfast At Tiffany’s.

“Our car broke down,” Ria moaned.

Em winked at me and whispered in my ear, “Okay, you’re one-for-two.”

“How long have you been waiting?” Ria asked, pointing toward a clump of royal palms in the distance where the car was parked. She looked stressed, so I asked if Ria needed a cigarette break in the shade before we headed off. She lifted her hand and flung her wrist contemptuously in one of my favorite indigenously universal Cuban gestures.

“I quit,” she said. “Too expensive. I gave up cigarettes and hair dye for the same reason. Too expensive! I haven’t even been anywhere fun in Havana for months. I can’t afford taxis.” Ria gazed at the airport and shook her head. “An airport full of people leaving and hardly anyone arriving. Let’s get out of here, it’s too depressing.”

Out on the highway, the Cuban dreamscape rolled out its topsy-turvy red carpet. This journey has always reminded me of Havana’s version of Tony Soprano driving home through the detritus of American decline–both glaring and subtle–at the beginning of every episode of The Sopranos. The creator of The Sopranos confessed the real joke of the show was never about a gangster going to therapy, it was about a country so selfish and narcissistic that even the mob couldn’t take it. Havana’s version of decay is different: savagely neglected buildings and structures crumbling down or caving in feels like a plague of invisible termites. The only Happy Meals on the island are 500 miles away at the McDonald’s drive-through in Guantanamo Bay’s military prison.

Ria began to tell Em about how much had changed since Obama’s visit: Trump reversing the thaw in relations, remittances to the island suspended, oil shipments blocked, Havana Syndrome giving Trump a convenient pretext to amp up sanctions and re-designate Cuba as a “state sponsor of terrorism,” that played a major role in delaying the development of Cuba’s vaccine by six months during the pandemic. Biden squeezed the restrictions even further, tightening the screws of the almost 62-year-old U.S. Embargo.

Tourism has been throttled. In the summer of 2021, shortages of food, medicine, and blackouts led to the largest demonstrations against the government since 1959. This time peaceful protestors had chanted “Liberty!” and “Patria y Vida!” instead of “Homeland or Death,” the motto Fidel popularized in 1960. Over 1400 protesters were detained during the protests; more than 700 reportedly remain in jail. Ria said there was less hope now than during the “Special Period,” after the Soviet Union collapsed, along with their subsidies to Cuba. Most devastating of all, the best and brightest had fled the island any way they could in an almost biblical exodus, maybe 600,000 to just the United States and Spain alone in the last two years.

I rolled down the window and leaned out into the clammy breeze to temporarily drown out any more details. I watched the balletic anarchy of Ladas and old beaten down American cars belching exhaust rumble over warped pavement as the occasional military truck with soldiers in the back sailed by. Hitchhikers were everywhere on both sides of the road. Nearly every minute we passed a broken down car or bus. Sometimes a one-man horse-drawn carriage clopped along the shoulder of the road past little stands selling garlic or strings of fish.

Ria turned to me, “Rethinking Havana as your choice to celebrate your anniversary?”

“Life is a joke to be taken very seriously,” was a Cuban adage I learned on my first trip to Havana. It didn’t take long to recognize there was nothing lighthearted about the sentiment behind it.

Before I had even stepped on the plane to visit Havana for the first time 24 years ago, my mother had insisted I look up some of her friends in Cuba. Startled, I asked why she had never mentioned anything about them before. “Darrrling,” she purred, in her impossibly thick Hungarian accent. “Because I haven’t met them yet. But you’ll see. They’re there.”

Looking at Ria’s face in profile as she smiled almost apologetically just scratched the surface of how bleak life here had become. I reflected on how many of the “friends I hadn’t met yet” I ultimately did meet in Havana over the years. Yet those same years had also taken and delivered nearly everyone I’d cared about on the island through revolving doors to somewhere else, a hundred or so Cuban Andy Dufresnes who managed to escape their tropical Shawshank Prison. OnlyRia, unwillingly, remained. Part of the reason my wife went along with Havana for our anniversary was to bring some money to help her. Ria refused to take anything unless we hired her as a fixer so Em could see as much as possible during our five-day trip.

As the light faded and royal palms silhouetted against the horizon, we passed the Plaza de la Revolución, its six-story high stenciled outlines of revolutionary heroes Che Guevara and Camilo Cienfuegos dimly glowing. A kettle of vultures circled over the José Martí Memorial tower like remnants of burnt paper over a fire. Peeking over the jungle, the flicker of the Habana Libre hotel’s penthouse lights turning on caught my eye. On my first trip to Havana I had made friends with an elderly Ricardo Montalbán-lookalike nicknamed Cucho who had worked Habana Libre as a doorman (back when it was known as the Habana Hilton) on the day Fidel and company arrived in 1959 to take over the top two floors as their government headquarters. In his old age he ran a CDR (Committee for the Defense of the Revolution) on the block where I lived. In Cucho’s mind, compared to how Cuba had been under an American-backed dictator like Batista, his island was a shimmering utopia. His children were far more conflicted. His grandchildren were not: they’d all left.

We drove toward Quinta Avenida to exchange money at a spot Ria had lined up. Ria took $200 from Em and exchanged it inside a tiny shop, little more than a gas station convenience store. She returned looking as if she’d robbed a train, carrying an arm full of Cuban currency, nearly 50,000 pesos. Em turned to me, “We’re going to need a briefcase.”

We arrived at our rented apartment overlooking the six-story tall U.S. Embassy and I watched Em and Ria look off toward the distant lighthouse rising above the Morro fortress. The malecón sea wall, always Havana’s windowsill and collective sofa, had hardly any of the usual silhouetted lovers embracing against the hurricane-season’s bruised sunset pastel sky and waves drifting in from the Florida Straits.

Ria pointed out foreign investment in an indeterminate future, inserted like throbbing tumors on the skyline. New hotels like the Grand Aston directly behind us and a 5-star monstrosity–the largest in the country–under construction called Tower K, looming directly opposite the Habana Libre. Ria scoffed and said all the fancy tourist hotels were basically empty, Havana’s Potemkin village. Along the malecón we watched a motorcade of shiny American 1950s convertibles carrying posing tourists taking selfies in the backseat.

The sunset beyond the selfie sticks reminded me of a woman I’d fallen hard for the last time I visited the island. If Cuba has a famous reputation for being frozen in time, a whiplash momentum exists for relationships that form with an acceleration and intensity rivaling wartime urgency. Havana’s nervous system responds to the atmosphere of a war zone despite the absence of any actual war. The woman hadn’t told me she was in an arranged marriage with a wealthy Swiss businessman and would soon leave to join him in Europe. “Beautiful sunsets require clouds,” she’d written me in a letter after leaving Cuba. “The fact our paths crossed doesn’t mean that we have the same path or even that our paths necessarily follow the same way for long.” On the flight home after meeting her there was a slight discrepancy with the headcount. The American Airlines cabin crew and Cuban airport refused to communicate for 11 hours to sort it out while every passenger on the flight melted down. I was the only person disappointed when the issue was finally sorted out and we took off. J.D. Salinger was on to something when he wrote, “Probably for every man there is at least one city that sooner or later turns into a girl.” For me, Havana had turned into her and I seriously doubted I could ever go back.

When Em connected her phone to the wifi, the person renting us the room texted, warning us about some recent muggings of tourists in Centro and Old Havana. Someone had even climbed from balcony to balcony to steal a laptop from a nearby Airbnb. In all my previous visits to Havana, some lasting long periods of time, I had never met anyone visiting who had ever experienced any form of violence.

Ria shook her head. “These are dark times. Massive food shortages. The pharmacies are empty. Blackouts. Hospitals are death traps. Mira, I have cavities in my mouth. It’s not just that all the dentists have left. Even the people on the street with dental tools and black market anesthetic who for $10 could help you with cavities in the past? They’ve left too!”

Em and I stared blankly at Ria.

“I’m not sure if you’re waiting for me to laugh or cry?” she threw up her hands.

We left the apartment and walked through the overgrown, leafy residential neighborhood of Vedado toward Old Havana. Ria wanted to show Em some of the hidden delights buried in the magical liminal spaces across town. Blocks of faded mansions filled with dilapidated elegance, the streets lined by palms and monstrous banyan trees, bulging roots tearing through the pavement in chasms. Concealed riotous gardens. Laundry strung above us over balconies. Beyond the handful of tourist-infested targets in Old Havana, one of the great delights of Havana is how rarely you run into anyone but Cubans. We stopped for a drink out behind the Hotel Nacional in the rocky gardens perched above the sea.

As we approached the Nacional’s entrance, Em asked Ria about how Cubans viewed President Miguel Diaz-Canel, the first leader in 60 years not named Castro.

Ria quickly gazed around to see if anyone was in earshot.

“His nickname,” Ria said in a hushed tone, “is singao.”

Em and I looked at one another wide-eyed and turned back to Ria.

“Motherfucker?” I asked.

“Shhhhhhh!” Ria protested. “People will know who you’re talking about! People have written it as graffiti and got years in jail.”

For the next two days leading up to our anniversary on October 8th, Ria’s plans for Em’s tour reminded me again how Havana supplied the definition of many of my favorite untranslatable words in foreign languages long before I’d ever encountered them. Retrouvailles, meaning “refindings,” a reunion with someone you deeply care for but have been apart from for too long, is a word that perfectly describes how I feel each time I see Ria’s face since meeting her for the first time 17 years earlier. Wabi-sabi, finding beauty in imperfections–scars–illuminated Havana’s sore heart, a jagged and gouged heart with so many pieces torn out and even more put back in. A heart that refuses to choose between the kind of beauty that gives rather than takes away: it does both simultaneously. Querencia, the place where we know exactly who we are. Safe ground. Higher ground. Duende was invented by the poet Federico Garcia Lorca, defining it as “a struggle, not a thought,” who spent only three months in Cuba yet declared, “If I should become lost… look for me in Cuba.” Maybe because if there was a watermark of the spirit of these people, the best I knew was meeting Cubans unable to walk who still remained convinced they could dance. Saudade’s aching double exposure of what Ada Ferrer called an “absent presence, a present absence,” felt so viscerally on both sides of the Civil War fought across 90 miles.

Ria got us once impossible reservations at La Guarida in Centro Havana, Cuba’s answer to Rao’s in New York City. Down the streets we saw men sipping rum and slapping dominoes on tables. From balconies bicycles and baskets were lowered to the street like Rapunzel’s hair by shoelaces. A dozen ghostly kids playing stickball on the corner, lit only by passing car headlights.

Mercedes with diplomatic plates used to park as close as possible to the restaurant entrance and people would drift inside the long flight of marble steps pirouetting like a flirtatious ballerina dancing alone under washing lines and broken statues and pillars. Now, like everywhere else, the place was half empty. All of Havana had transformed into a hundred thousand melancholy Edward Hopper paintings.

Hemingway’s El Floridita on Calle Obispo was the only place in town that was crowded, mostly with Russian and European tourists. Their once incredible cocktails tasted like dish water. Ria took a sip and abandoned her daiquiri almost immediately. “Didn’t I warn you?” she shook her head. “Any government owned place is mierda now.” Outside on Obispo, formerly humming with luxurious shops rivaling any cosmopolitan city in the world, just a ghostly corridor. Empty bar after empty bar. Nearby, Ria showed us the aftermath of the Hotel Saratoga gas explosion from last year which killed 47 locals while undergoing renovations. Madonna and Beyonce and Jay Z had all stayed there when they visited. Kid Chocolate Arena, the greatest place I have ever watched sports in my life, had been bulldozed to make way for a Chinese-financed hotel overlooking El Capitolio where portrait photographers with 120-year-old cameras had lingered on the front steps.

The next afternoon Ria introduced Em to the vibrant secret life that existed above the streets on rooftops, azoteas, quoting Dulce-Maria Loynaz, “The azoteas of the city caught in the tremulous thread of kites.” Many of Havana’s quiet residential neighborhoods have essentially transformed into open air flea markets of the lowest common denominator: shot glasses of coffee, loosey cigarettes, pens, toilet paper, watch parts, shoe polish, toiletries, nail clippers–seemingly everything but the bottle of water Em tried to find to combat the heat. On a wide boulevard behind the ornate university campus and Napoleon Museum, we encountered the first homeless people I’d ever seen in Cuba. Then a dejected succession of hundreds and hundreds of beggars and cripples. Nothing out of place from anything seen today in Los Angeles or San Francisco, but previously unimaginable here.

We visited my old boxing gym in Old Havana, Rafel Trejo. My old trainer, Héctor Vinent, a two-time Olympic champion, had rejected millions to leave the island. When Héctor fought internationally, American promoters would sit ringside and crack open suitcases full of cash. They would throw crumpled pieces of paper into the ring with offers of vast fortunes if he was willing to sign a contract.

After we built up some trust and I asked him about it, he told me no matter how much money was on the table, he just couldn’t abandon his five kids. “The United States is like a girl who is in love with you,” he once told me, laughing under his breath. “But you don’t like her. You have to ignore her. You have to resent and lament living the rest of your life based on memories.” When I first arrived in 2000, there were no foreigners training with Cubans in the open-air facility. This afternoon there were only foreigners. I asked to use the bathroom and they laughed, telling me, “No running water for four months.” I discovered Héctor was long gone, living in Istanbul.

In 2007 another two-time Olympic champion, Guillermo Rigondeaux, had stumbled in on a training session I had with Héctor in this same gym. Fidel Castro had branded him a traitor and Judas to his people for trying to leave. He had committed social suicide. There was a prominent gold grill over his front teeth. Making small talk, I asked where the gold came from. “I melted my gold medals into my mouth,” he said, pulling on his cigarette, casually handing me a professional life as a writer exploring his homeland through his tragic story.

Teofilo Stevenson and a friend

Strolling the next afternoon along the malecón, turbulent stormy waves lifted clouds of spray above a trickle of gasoline rainbows in the gutter. A journalist in 1937 once described the malecón as “made of fragments of creole sun, of tropical moonlight, the faces of lovely women, explosive laughter, soft singing and the blue-green offerings of the sea by its side murmuring its whispers of endless passion.” Looking down side streets into the city, eroding neo-everything architecture looked on stoically as stray dogs chased taxis through dust clouds. Ria told us nearly all the funding for cultural events or sports had been massively cut back.

We wandered over to Estadio Latinoamericano, where Obama had watched a few innings with Raúl, to look for a few local baseball souvenirs from the gift shop. Shuttered. A flash heavy rain fell and we ducked under the cover of a balcony on a side street while an argument between neighbors led one party to return to his house and retrieve a machete.

We had a nice dinner in Vedado that night and woke up on the morning of our anniversary with food poisoning as Em learned that relatives of her co-workers had been murdered by Hamas. The father of the Israeli founder of the startup had been killed during the Yom Kippur War 50 years earlier. The company has an office in Tel Aviv and five employees were called into the reserves almost immediately. In between bouts of vomiting, Em spent the rest of the day in bed reaching out to co-workers and doom scrolling the carnage on her phone. I called Ria to back out of our plans that day but she insisted on coming over. She went door to door trying to find Tylenol or anything else to help with our fevers. She arrived with a concerned neighbor who brought medicine and was insulted when I offered to pay him for his kindness. Almost on cue, out our window I watched someone take the arm of an elderly woman and help her across the street, both laughing tenderly at the exchange. There are no sights to see in Cuba that remotely compare to the endless acts of everyday decency and humanity these people extend by instinct despite such abject struggle.

Being bedridden for hours delivered a sad feeling of relief. Tourism is life lived in the parenthetical. I hadn’t expected sharing Havana with my wife to feel like introducing her to a comatose beloved relative on life support. However many hundreds of thousands of Cubans had left, Cuba as a symbolic window hadn’t shattered with the escape just yet. Instead of broken glass, there is just the shape of the hole left on the island. Without the window shattered entirely, it was impossible to avoid tracing that overwhelming absence along the shards.

That night I’d recovered enough to make good on a promise I’d made to drop off a little package to a British journalist named Ed Augustin living and working in Havana, a few minor things to help fix his broken electric keyboard. I walked into town through Havana’s lifeless streets and turned out of Barrio Chino toward the Prado promenade, my favorite street in the world, shaded by a long canopy of trees and filled with birds.

I got to the Hotel Inglaterra a little early. Lorca had his last meal in Cuba at the Inglaterra during an almost apocalyptic Caribbean downpour. Graham Greene sent an agent to stay there in Our Man in Havana. I used to walk miles into town a couple hours before dawn to get breakfast at the Inglaterra. Nothing else was open for insomniacs. A waiter would play Ernesto Lecuona on the piano for me. Across the street in Parque Central, even the beloved Esquina Caliente group of baseball fanatics who argued at all hours were gone.

I ordered a coffee to go with a blackmarket Romeo y Juliet cigar I’d bought on the street to help with the lingering taste of vomit in my throat. I wondered about faces I’d known and cared about here getting older somewhere else. Sometimes the years rustle and stir in your mind like leaves blown across the paths of Central Park on a windy day. Just then a group of local kids leaned over the railing of the Inglaterra’s cafe and, wild-eyed, glared at me. I gave them whatever I had in my pocket but they still believed I owed more. They demanded the packets of sugar I hadn’t used with my coffee, and pouches of condiments from an uncleared table. I was retrieving those when Ed Augustin arrived in flip-flops.

An especially obnoxious crowd of drunk tourists piled into the area, passing around bottles of rum. Even worse, a touring band quickly set up and began playing an unironic version of “Hotel California,” probably my most hated song in all of popular music. Until that exact moment I had never begrudged the total lack of gun violence in Cuba.

I pleaded with Ed to go anywhere else to help my nausea and headache. We found an empty bar off the Prado. Ed touched on everything Ria had mentioned about what contributed to the visionless, rudderless society Cuba had become in the years since Obama’s visit, a perfect shitstorm of factors from the sanctions to the pandemic. He blamed 70% of the situation on the American embargo against the island (Ben Rhodes later told me he found this estimate conservative).

“During the financial crisis of 2008,” Ed began in the new bar, “the British economy shrank by 5%. Which was considered massive. Here it might be half. And half of everything the government spends is fuel and food. They’ve got nothing. They’re broke. To a large degree, it’s sanctions. They can’t maneuver. What government in the world could deal with this? This massive exodus of Cubans means all the talent has left the country. The government can’t recruit anybody because the salaries are shit. So the government gets the dumbest and the true believers. Everyone is sad. Everyone wants to leave. It just gets to you.”

Three hours after I promised Em I’d be back, I finally returned to our apartment, blamed Ed for being far too interesting, and collapsed. Ria arrived the next morning with her neighbor and his car ready to take us back to the airport. I had another of the Romeo y Julietas I’d bought in the street and asked if Ria would share it with me before we said goodbye.

My other best Cuban friend, who like Ria is family for me, left Cuba in 1995 when he was nine. He joined his mother in the Cayman Islands before coming to Los Angeles at 20, where he painted houses in Compton for under the table wages. I met him at a boxing gym in Los Angeles. The first thing he did when he looked around the room was smile. “I’m not alone,” Jorge laughed. “We have some Cubans here.”

I saw thirty Latinos in the room, but certainly nothing identifiable suggesting anything Cuban about any of them.

“How do you know any of them are Cuban?” I smiled, incredulous.

“Because Cuban eyes often look close to tears,” he said matter-of-factly. “Tears never seem far away because the pain and joy is too close to the surface. Cuban eyes always look emotional. I can always spot them in a room.”

I had never heard the open wound that defined so much of the Cuban character and tide of emotions distilled to such a profound essence.

I told Ria that story and asked a question that had troubled me for the entire trip.

“This is the first time I’ve been here where what Jorge said about Cuban eyes wasn’t true.”

“Of course it isn’t true anymore,” Ria said, relighting her cigar. “Qué va. Mira. How do you expect our eyes to look close to tears when we have no tears left?”

Later, after the goodbyes with Ria, as Em and I were in the car headed to the airport, I told her what Ria had said.

Em asked me if I’d ever heard of an experiment conducted at Harvard during the 1950s. For the "Hope" experiment, they placed rats in pools of water and waited to see how long they could tread water before giving up. The average rat drowned in 15 minutes. Then they tested another rat but rescued it just before it gave up. After the rat had recovered they put it back in the water for another round.

“How long do you think it lasted?” Em asked me.

“This is way too dark after this anniversary from hell.”

“Sixty hours,” she said. “This whole trip has felt like Cuba is in the 61st hour.”

Brin-Jonathan Butler has written for Esquire, Bloomberg, ESPN Magazine, Playboy, Harper’s, The Paris Review, Southwest: The Magazine, Al Jazeera, and Vice. His first book, The Domino Diaries, was shortlisted for the PEN/ESPN Award for literary sports writing and was a Boston Globe Best Book of 2015. The Grandmaster was published by Simon and Schuster in November of 2018 and long-listed for the RBC Taylor Prize, Canada's most prestigious non-fiction literary award.

Our man on the malecón

Grupo Sierra Maestra

Estono leiva bata : Los Patines

Bebo Valdes & Diego El Cigala : Lagrimas Negras

Como Mi Ritmo No Hay Dos ::: Cachao

Medley from Cuban TV ::: Los Zafiros

Sueno Con Serpientes ::: Silvio Rodriguez

D'Palo Rumba : Los Munequitos de Matanzas

Smoke Gets In Your Eyes :::: Cuarteto de Saxophones

Havana Moon ::: Chuck Berry

La Bella Cubana ::: Camerata Romeu

La Comparsa ::: Ernesto Lecuona

Black Chicken 37 ::: Buena Vista Social Club