Castro waving to his adoring fans upon his arrival to New York City in 1959 (Credit: Credit: New York Daily News/Getty Images)

Fidel Castro’s secret love affair with NYC

On a recent sun-drenched afternoon, I was wandering the leafy blocks of West 82nd Street near Central Park, when I came to number 155, a stately Victorian brownstone with a carved stone stoop. Not so different from 1,000 other addresses on Manhattan’s Upper West Side, I thought – except that this is where the young Fidel Castro, a then-unknown 22-year-old Cuban law graduate, stayed on his honeymoon in 1948.

It was Castro’s first visit to the US and he fell in love with New York immediately

Castro had been a vocal student leader back in Havana, but there was nothing in 1948 to indicate that he would soon lead a revolution on his home island and become one of the most famous and divisive figures of the 20th Century, thrusting Cuba into a bitter Cold War feud with the United States that continues to this day.

It was Castro’s first visit to the US and he fell in love with New York immediately. He was fascinated by the subway, the skyscrapers, the size of the steaks, and the fact that, despite the rabid anti-Communism of the US during the Cold War, he could find Karl Marx’s anti-capitalist jeremiad, Das Kapital, in any bookstore. Castro and his alluring high-society first wife, Mirta Diaz-Balart, stayed for three months in this charming apartment building, which still stands opposite a Ukrainian Orthodox church and close to bars filled with Columbia University students. Nothing much has changed on the quiet block in seven decades – except, of course, the rent.

This Cuban love nest was a key first stop in my quest to piece together a series of forgotten visits Castro made to my adopted hometown before he became demonised by Americans in the 1960s. His left-wing reforms would soon bring him into the arms of the Soviet Union – an alliance that led to the Cuban Missile Crisis in October 1962, the closest the world has ever come to nuclear annihilation. But my excitement at finding Castro’s long lost tryst pad paled in comparison to what I was about to discover only a short walk away on Amsterdam Avenue: his revolutionary office.

When Castro came back to Manhattan in 1955, seven years after his first romantic sojourn, he’d become renowned among Cuban exiles as an idealistic and slightly crazy firebrand for staging a failed uprising against the island’s dictator, Fulgencio Batista. By then aged 29 and divorced from Diaz-Balart (she had found love letters to another woman while he was in prison for leading an armed revolt and an attack on a barracks in the eastern city of Santiago), Castro came to New York to raise funds for a revolution from the city’s Cuban community, which was bigger than Miami’s at the time.

Flush with donations, the charismatic resistance leader opened an office for his rebel organisation, M-26-7 (The 26th of July Movement, named after the date of his failed uprising), on the Upper West Side, which was then better known as a buzzing bastion of progressive thought than an exclusive enclave for wealthy liberals, as it’s commonly known today. Staff hung the Movement’s black-and-red flag from the top window and handed out pamphlets to American sympathisers, who grew in number after Castro and an armed band of guerrillas – including a young medic named Che Guevara – crash landed in Cuba on 2 December 1956.

I had found the office’s address on an old leaflet, so I eagerly followed the street numbers along Amsterdam Avenue, until I spotted number 305, between 74th and 75th streets. The building was now, of all things, a Chinese massage parlour. No matter. It fit the description in historical eyewitness accounts exactly. I dashed up the steps and burst through the door, where the attendant smiled at me politely.

Did she know, I asked breathlessly, that this was where Castro’s sidekicks had once greeted New Yorkers fascinated by his romantic uprising? Under US law, the Cuban rebels were allowed to accept cash donations for the revolution but not recruit soldiers. Even so, many Columbia students did turn up at the door to offer their services as guerrillas – but only during their summer breaks, they insisted. They had to be back when classes started in autumn. 

The attendant smiled at me as if I were demented and said, very slowly: “I don’t speak English.” An older Chinese man then burst out of a massage booth. “Be quiet!” he hissed. “You’re disturbing clients! You want a massage or what?”

[Castro's] 1948 and 1955 visits were just the start of his love affair with the city

One of the classic pleasures of travel is to follow in the footsteps of famous historical or literary figures. I’ve chased Georgia O’Keeffe around Hawaii, Lord Byron in Switzerland and Leon Trotsky in Mexico City, to name a few. For me, it’s a win-win situation. If the quest leads to a well-worn tourist site, the historical story provides a fascinating extra layer that allows me to see it with fresh eyes. But most often, it leads me to places I would never have otherwise heard about, let alone visited. The connection can be revealing, or it can be ironic or even comical – like finding that Victor Hugo’s favourite brothel in Belle Époque Paris had been turned into a college dorm. But nothing quite prepared me for the unpredictability of following young señor Castro around New York.

The idea came to me while I was researching my book ¡Cuba Libre!: Che, Fidel and the Improbable Revolution That Changed World History. For two years, I commuted from my East Village apartment to Havana to dig through musty archives and interview nonagenarian guerrillas. But when it came to understanding Castro himself – one of the 20th Century’s most extraordinary and charismatic figures – I was surprised to find that the richest sites might actually lie only minutes away from my own home, in the citadel of American capitalism itself.

This revelation jolted me out of a certain lethargy. At the time, buried in writing about Cuba, I had become a little indifferent to New York and tended to keep to within a 10-block radius of my apartment. Now I had a reason to explore the city again, heading to such remote, exotic locales as the Upper West Side. Standing outside the Chinese massage parlour, I could suddenly imagine Castro before he was fixed in the world’s imagination as a Cold War cliché. Instead, I could see him in his 20s, a tall, athletic figure – startlingly clean-shaven, except for a pencil moustache – rushing about New York with manic energy, astonishing strangers with his penchant for nonstop talking. And his 1948 and 1955 visits were just the start of his love affair with the city.

Everything changed for Castro after his guerrillas’ surprise victory in Cuba on New Year’s Day, 1959, when Batista and his cronies fled Havana in DC-4s like thieves in the night. A week later, Castro entered Havana triumphantly to delirious crowds reminiscent of the liberation of Paris, promising to drop the reins of power once stability was restored and usher the island into a democratic future. Castro became an international celebrity, and he and his rebels – known as Los Barbudos (“the bearded ones”) – were idolised by yanquis (“Americans”) as young, sexy liberators. As a result, his most surreal visit to New York came only four months after his victory, in April 1959, when “El Comandante,” as Castro was called, swept into town for five days as a conquering hero.

Castro was now as big as Elvis, and was mobbed by New Yorkers from the moment he arrived at Penn Station. Newspapermen compared him to George Washington; women swooned. (“Fidel is the best thing to happen to North American women since Rudolph Valentino,” sighed one.)

It took 20 minutes for the New York Police Department just to usher the 32-year-old hero – instantly recognisable in his trademark khaki fatigues, forage cap and cigar – the 100 yards across Eighth Avenue to his hotel, in part because he kept jumping through police barriers into the crowd to shake hands, saying, “I must greet my public!”.

It’s easy today to follow Castro’s itinerary. The majestic old Penn Station where he arrived was notoriously demolished in the 1960s, but the Hotel Pennsylvania, where he stayed and which was designed to mimic the famed station across the street, still looms. Its hulking colonnaded facade has hardly changed, and the interior is preserved in a sort of charming Mad Men-esque time capsule.

Seventy years ago, Castro played tourist in New York City, and this was my chance to revisit classic Big Apple attractions I had ignored for years. He went up the Empire State Building, and so did I, beating the crowds by going at 23:00 and lapping up the Art Deco ambiance. And in Central Park, I paid my respects at the Naumburg Bandshell, where he spoke to a crowd of at least 16,000.

New York’s legendary museums, however, were not on the agenda: Castro was a voracious book-lover but indifferent to the visual arts. He ignored suggestions to visit The Museum of Modern Art and went to the Bronx Zoo instead, where he delighted reporters by poking his hand into the tiger’s cage and devoured a hot dog, declaring the zoo, “The best thing in New York”. I, too, schlepped there. The tigers now live in a sprawling landscaped environment, so I couldn’t get anywhere near them to imitate Castro’s macho gesture. The zoo’s hot dog, however, was still delicioso.

New York's Cuban-Chinese cuisine

On his hugely popular 1959 visit, Castro vanished from his hotel late at night to visit diners. He had a fondness for “Cuban-Chinese” cuisine, an unlikely fusion created in Havana by Chinese immigrants. Ironically, most of Cuba’s Chinese immigrants fled Havana in the early 1960s when Castro became more radical, and many of them opened Cuban-Chinese diners in New York City. This fusion soon became a staple in New York, and while most have disappeared in recent years, a few have held out.

Here’s where to try them:

• La Caridad – an Upper West Side institution since 1968

• Calle Dao – a relative newcomer with locations in Chelsea and Bryant Park

• Rincón Criollo – located in Corona, Queens, this is one of the most famous ones left, serving Cuban-Chinese since 1976

New York’s love affair with Castro did not last – at least not among white, middle-class residents. When Castro returned to address the United Nations in September 1960, the bitter split between the US and Cuba, which began largely over Castro’s economic policies, was well underway, as Castro became more radical and Washington more vindictive. The following month, US president Dwight Eisenhower would issue what has become the world’s longest-standing economic embargo on Cuba, and had already begun authorising the first of several hundred unsuccessful CIA attempts to assassinate Castro and overthrow his regime.

As Castro arrived to speak at the United Nations, the New York press mocked him as “El Beardo” (a non-Spanish jab intended to mean, “The Bearded Guy”). And just one year after being swarmed by a sea of admiring spectators in Midtown Manhattan, he was now jeered in his car by angry pedestrians.

After a fight with the staff at his Murray Hill hotel, the Shelburne Hotel, Castro famously threatened to camp in Central Park before moving his entire entourage to Harlem, which had long been considered the capital of Black America. He was the first foreign leader to ever stay in the neighbourhood, and many African Americans, who admired that he had declared an end to racial discrimination in Cuba shortly after assuming power, welcomed him with open arms.

I was delighted to find that the Shelburne Hotel still exists near the United Nations Headquarters. I made the pilgrimage to Lexington Avenue and found its regal old-world exterior unchanged. It’s certainly a friendly place today: at 17:00, the doorman greeted me with a cheery smile: “Just in time!” I wasn’t sure what he meant, until I saw a clerk handing out free happy hour wine. He seemed not to care that I wasn’t a guest, so I happily perched on a linoleum sideboard with a glass of Chardonnay among travellers killing time before evening flights. I asked the doorman, an African immigrant named Raymond Larry, if he knew that señor Castro had once caused a ruckus in the hotel.

“Of course,” he laughed. “The Cubans were keeping live chickens in the rooms!” Larry said he had worked at the hotel for 15 years, and had heard the stories of 1960 from elderly doormen present at the time. “Castro was cooking them up and throwing the bones out the window. They landed on people’s heads! It was crazy!” A comic confrontation ensued, Larry explained, as the hotel managers allegedly demanded a $20,000 security deposit (roughly $165,000 in today’s money) for possible damage.

In a huff, Castro took his 60-strong Cuban contingent far uptown, taking over the Hotel Theresa around the corner from the Apollo Theater on 125th Street in Harlem. It was a snub to the establishment and a declaration of support for African Americans on the cusp of the Civil Rights Movement. He felt more at home among the “poor and humble people of Harlem,” he declared.

El Comandante again showed his flair for PR by meeting with Malcolm X while 2,000 Nation of Islam members rallied in the streets outside the hotel. Castro’s huge crowds continued to grab daily newspaper headlines, much to the annoyance of Eisenhower. The Cubans held a chic party attended by artists like poet Allen Ginsberg and photographer Henri Cartier-Bresson, and when Eisenhower failed to invite Castro to a luncheon for Latin American heads of state, he hosted his own grand feast – treating the Theresa’s “proletarian” African American staff to steaks. Photos show the bellboys and desk clerks all sitting next to Castro at the lunch table, still wearing their uniforms.

Today, the 13-storey Theresa building is listed on the National Register of Historic Places. As I made my way up a stretch of Seventh Avenue lined with vendors in colourful, patterned African garb, I found the building’s exterior as splendid as ever – not for nothing was it known as “The Waldorf of Harlem”. Sadly, the hotel’s once-grand interior was turned into condos and offices in the 1960s and renamed the Theresa Towers. A bemused doorman broke the sad news of the renovation to me. The majestic old ballroom and dining room had been gutted, he said. “Really, there is nothing to see.”

In Harlem is where I have my best friends

Still, I reasoned, perhaps I could dip into old Harlem itself and recapture the neighbourhood’s “Fidel fever” of 69 years ago. At night, Castro and his followers – many of whom were young Afro-Cubans, including the head of the armed forces, Juan Almeida – would go out to Harlem diners to eat cheap, hearty burgers, and there are marvellous photos of waitresses flirting and laughing with them. On one occasion, the Cuban foreign minister Raúl Roa posed for photographs while eating a hot dog at the Chock-Full-o’-Nuts on the corner. 

Fidel’s 1960 speech at the United Nations is still a record. Clocking in at nearly 4 hours and 29 minutes, it was a ringing denunciation of imperialism. From then on, relations with the US slid precipitously. The CIA-backed Bay of Pigs invasion the following year marked a definitive break, with Castro throwing his lot in with the Soviet Union and the Socialist model. Castro came back to New York three more times in 1979, 1995 and 2000, always to visit the UN – which forced the US to give him a visa. But he never forgot the heady days of his 1960 trip. Four decades later, on his 2000 sojourn, he gave an epic speech before a congregation of 3,000 at Riverside Church, not far from his old digs at the Theresa Hotel, noting that “In Harlem is where I have my best friends.”

Yet, turning away from the Theresa, I soon realised that many of the old Harlem businesses Castro and his cronies might have visited in 1960, like theonce-iconic Lenox Lounge, are gone. Other Harlem institutions, like Sylvia’s Restaurant – the so-called “Queen of Soul Food” – opened its doors just after Castro’s visit, in 1962. Instead, I settled for a drink at a nearby restaurant called Red Rooster. Located a block from the Theresa, it was emblematic of the new Harlem: it takes its name from a legendary neighbourhood speakeasy that once attracted jazz greats and Harlem-born novelist, playwright and activist James Baldwin; now it’s a sleek, loft-like dining room headed by a Swedish-Ethiopian celebrity chef.

I didn’t mind. In fact, it was as unpredictable as everything that involved following Castro around New York, a city whose appeal has always been its constant reinvention. Back home in the East Village, I threw myself back into writing my book. New York’s ebb and flow seemed to echo the chaos of history, helping me get into the mind of the Cuban leader when he was still in his prime, and the future was fluid and unformed.

More than anything, my Castro scavenger hunt had rekindled my fascination with my adopted hometown. In the end, it didn’t really matter whether his historical haunts were miraculously intact or had vanished like mirages. I had explored corners of the city I had never imagined, and chatted with people I would not have otherwise met – which is, after all, the essence of travel itself.

A lot has been written of late about New York being “over” – that high rents and gentrification have emptied the city of its allure. But it was a relief to find that the opposite is true: the city may not be what we expect, but it is still as bottomless as ever. 

Tony Perrottet is a writer, historian and author of the book ¡Cuba Libre!: Che, Fidel and the Improbable Revolution That Changed World History. 

Travel Journeys is a BBC Travel series exploring travellers’ inner journeys of transformation and growth as they experience the world.

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