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Tropic of El Jefe

We had come to Cuba as lovers and newlyweds to discern the truth of the often repeated and reported claim that Fidel Castro is the world’s greatest lover. How many Cuban cigars did we buy, trying to discover the secrets of Castro’s love life? We...

All illustrations by Jonny Negron

Everywhere we went in Cuba, men tried to sell Wes cigars. They approached us on the sidewalks, at cafés, and while we were riding in their cars. The come-on was always the same: they would smile and say hello.

For weeks, we fell tentatively into this line of conversation, which led to the inevitable sales pitch.

A man was walking with his wife and his daughter. He overheard us wondering about a line of people outside a door.


“That’s Los Nardos,” he said. “Best restaurant in Cuba. For the locals. Floridita, Hanoi—those are for tourists. No offense.”

We told him it was fine.

He talked a bit more. He welcomed us and asked us where we were from, and when we told him we were Americans, he said, “Our governments don’t get along, but we are just people.”

He continued to make casual conversation. He asked us what our plans were, how long we planned to stay in Cuba. He reached for conversation, and then he said, “Do you like to smoke cigars?”

“Yes,” Wes said.

“What is your favorite cigar to smoke?”



His wife tried to pull our cigar salesman away. He said, “You know it’s a special this week. I have.”

We had come to Cuba as lovers and newlyweds to discern the truth of the often repeated and reported claim that Fidel Castro is the world’s greatest lover. How many Cuban cigars did we buy, trying to discover the secrets of Castro’s love life? We quickly lost count.

Once our questioning of the locals led us into a long and confused discussion of the construction of the Museum of the Revolution. Another time, a woman—after we’d bought her dinner and maybe a few too many drinks—gave us a long-winded impromptu lecture on each of the black-and-white photographs in the hotel lobby and then tried to take us on a tour of the Bacardi building.

But occasionally we gleaned a bit of helpful advice. The doorman at the Hotel San Basilio—after overhearing our discussion with a garrulous old Australian man in the hotel’s lounge who gave us one of his cigars—pulled us aside. He told us that one of Fidel’s great former mistresses was a dentist at the best dental clinic in Santiago de Cuba.


Photo courtesy of Hulton Archive/Getty Images

During an interview for her widely read 1993 Vanity Fair article on Castro, journalist Ann Louise Bardach asked El Comandante how many children he had sired. “Almost a tribe,” he answered. We called Ann Louise to ask her what else she could tell us about Castro’s love life and about her book Without Fidel, which includes a family tree that traces a small portion of Castro’s progeny.

“Like most Cuban men, Castro viewed having sex as an entitlement,” she told us. “Sex, after all, is Cuba’s national sport. He had affairs or slept with all kinds of women—he even had a son with one of his ministers’ wives, or so it was commonly believed. ‘Sin verguenza,’ as they say. ‘Pretty shameless.’ Some of these women thought that they were the one true love. I even know one who dodged his handler charged with managing his conquests. "No one knows how many women he’s slept with, probably not even him.”

“Was it just an overactive libido? Is he insatiable? Did you sleep with him?” we asked.

“Good God, no,” she said. “Though a few folks speculated about that, and the Miami Herald hinted about his reputed flirtatiousness, but it was all professional—even though the interview began after midnight.”

Wes raised an eyebrow at me like, Uh huh. We had her on speakerphone and were looking online at a picture of Ann Louise and Castro during an interview session. She was a hottie.


“I understood I could never begin to explain to him the why and the how of the Monica Lewinksy–Clinton scandal,” she continued. “He was truly baffled as to why having too many girlfriends could be a political liability. I think for him being a mujeriego, or womanizer, as a Latin man was connected to political power. Originally, his political power came from his first marriage to Mirta Díaz-Balart, mother of his eldest son, whose family was politically powerful, whereas Fidel’s father just had money but zero culture. Fidel did not remarry again until after [his second wife] Dalia had given him five grown sons, which was exactly the m.o. of his father, who did not marry Fidel’s mother until long after she had six children with him, not to mention the son he had with a woman who worked on their finca [estate].

“A friend of mine had an affair with Fidel when she was 15 or 16 and said she recalled being on the balcony of his room on the 23rd floor of the Habana Libre hotel. Fidel said to her, ‘One day soon every Cuban will have a car of their own.’ Kind of funny as most are lucky to even have a bicycle.”

In 2008 the New York Post reported—probably erroneously, as we learned in our investigation, but the claim persists—that Castro had slept with some 35,000 women. Three years later the Daily Beast reported that he “had one for lunch and one for supper. And sometimes he even ordered one for breakfast.” Many Cubans affectionately call him El Caballo (“the Horse”), a nicknamed he earned in the early 60s because of his reputation as a prolific and virile lover.


As of 2002, there were roughly 6 million women in Cuba. Of those 6 million, we figured there were probably at least 1 million Fidel would find, or would have found, fuckable. We attempted a statistical likelihood of an 87-year-old man having the wherewithal and time to make love to 35,000 women over the course of his life but were unable to come to a precise conclusion. So instead, we decided that field research was the way to go and traveled to Cuba where, we reasoned, over the course of a month we could find at least a few hundred women who would tell us what Fidel was like in bed.

Neither of us had visited a totalitarian country before. Excited about our story, we entirely forgot that it’s risky to ask questions about the former ruler of the regime. The days of the beard-stroking hand gesture are over (Cubans used to run a hand through an imaginary beard to refer to Fidel, in case anyone was eavesdropping), but still, if the Cuban government heard about two Americans snooping around El Jefe’s supposedly lecherous past, things could become problematic.

The Telegraph reported in 2010, “Discussing [Fidel’s] womanizing ways is strictly taboo on the Caribbean communist outpost.” But a friend and expert on Cuba (who also happens to be a VICE contributor) told us that it wasn’t such a big deal when we wrote to him asking for advice. It was several months before our departure, and he said that Fidel’s love life was one subject that was entirely safe to discuss, although getting a Cuban to go on the record about it might be challenging. Another friend with insider knowledge of the country told us that stories of Fidel’s love life were the stuff of legend. “Everybody in Miami has a cousin,” she said—“cousin” meaning an illegitimate child of Fidel’s.


However, when we got to Cuba and started asking around, we found that the women in the streets are not so eager to speak in detail about Castro’s sexual exploits. Completely understandable, of course, but we went back to our Cuba-expert friend and said we were having trouble. He wrote back, “In Cuba, talking about the government isn’t healthy.” Ann Louise commented, “Women simply will not talk about their affairs with Castro, because it will have direct effects on them if they are still in Cuba. I lost my visa by writing too candidly about his personal life.” Why didn’t we know this before we got to Cuba? Well, Castro loves—or at least loved—to speak publicly about his erotic exploits. Would anyone else in Cuba dare to do the same?

Desperate, we took the advice of the doorman at the Hotel San Basilio, and Wes volunteered to receive Cuban dental treatment. “I’ve got a cavity or two anyway,” he said. But we had not anticipated the social awkwardness of asking a woman who is drilling into a tooth about her sex life. We had presumed Wes would do most of the talking, but naturally he couldn’t, with her hands in his mouth. It took Holly some time to explain to the dentist that we were journalists, which was a risk because we were traveling under a tourist visa.

The dental clinic was on the second floor. The dentist was a well-groomed woman in her 60s. She was about five feet tall. She had her hair dyed brown, and she wore a little touch of makeup. She smelled nice. Her assistant was the same age and height, but a bit less feminine. The dentist wore nursing shoes, a skirt that came below her knees, and a patterned blouse and lab coat. Her assistant wore a plain cotton shirt, cotton pants, and a blue technician’s coat. The dentist’s hair reached her shoulders, and the assistant had hers cut short.


Abruptly, and despite all of our shamefaced conspiring and hand-wringing, it was the assistant who steered the conversation toward the subject of love. Wes had begun to bulge his eyes and make faces. Holly had gone around to kneel at the foot of his dental chair. She had a hand on his shin. The dental assistant smiled. She said, “Men always think the best. Women not.”

“Are you married?” Holly asked.

She nodded.

Holly shifted her head to address the dentist: “And how about you?” The dentist had a mask over her mouth, its upper edges butting up against the rims of her glasses. She had her rubber-gloved fingers in Wes’s mouth. She nodded.

“We came here to write an article about Fidel Castro,” Holly continued.

Wes tried to shake his head; the dentist put a firm hand on his cheek. “Don’t move,” she said.

“He was married for so many years,” Holly said, “but he claims to have had so many lovers.”

The assistant didn’t look up at her boss, but her motions, which had been fluid, became noticeably self-conscious. She started to move like an inexperienced actor cast in a scene beside Robert De Niro.

Holly said coyly, “What must his wife have thought…”

The dentist didn’t miss a beat and said, “She was glad for the break.”

The dentist’s assistant clarified: “He’s had at least three wives. Depending how you count.” Then she took Wes to get X-rays in the room next door.

“Your doctor. For two years,” the dentist’s assistant told Wes. “Don’t worry. Let your wife ask the questions. The women will tell you the truth. She was with him for two years. Her husband is dead now. So she can tell you everything. We were friends. We were at a different clinic then. A car would come to get her. She would be gone for an hour or two. Then, she comes back to work. She was happy. She was very sad when it ended. But her husband could do nothing. Many men in our country suffered this. They admire him, but of course it is not easy for them. Their wives, their mothers, their daughters.”


We asked the dentist if she would join us for dinner. She declined.

Fidel Castro and his current wife, Dalia, live in a small house in western Havana. Visitors say it is furnished simply with Cuban handicrafts. It is not luxurious, but Fidel does have a big TV. He is incredibly private; even the CIA does not know much about his personal life. He is 6'3" and was married twice. As Ann Louise Bardach and others have reported, his first marriage ended because of his infidelity.

During the revolution, before the attack on the barracks at Marcada, a young Fidel began to exchange letters with a society girl named Natalia Revuelta. Natalia was married to a cardiologist, and Fidel to the niece of the minister of the interior, but after meeting in person, lightning struck and they fell in love. Alina Fernández is their daughter, born out of wedlock and raised by Natalia and her husband.

After the revolution, Fidel would visit Natalia at her home. Alina was a toddler, so her memories are patchwork, but she clearly remembers watching as her father’s hands began to tremble after the government closed his practice—doctor’s offices were considered private enterprise. (It is unclear whether the practice was closed because it smelled too much like capitalism, or whether it was just an instance of petty tyranny on the part of Fidel.) Castro would show up after midnight, in a cavalcade of jeeps, to make love to her mother under the same roof as her “father.”


When Fidel began having sex with Natalia’s friends, her mother complained to him. She asked him to have some respect for her daughter, and he said, “Don’t worry, I didn’t take off my boots.”

We traveled around the country and everywhere we went, the women stonewalled us. They would roll their eyes and change the topic or hurry away. We asked mostly middle-aged women and older, thinking that they would be more eager to talk about youthful indiscretions (also, it’s been at least a couple decades since Fidel was in his prime). No dice. Our Spanish is a little rocky at best, so the kind of delicate questioning required for this subject was far outside our range, but we forged ahead anyway. Once or twice we got a hint that led us to another town, or a restaurant or bar. Often we suspected that our potential informants were just trying to trick us into buying them a meal.

We had been in Cuba almost a month, and the dentist’s joke was the closest we’d come to an actual story. It was dry like the Sahara. We had traversed almost the entire island, and we were beginning to panic. We had walked into government offices and been brushed off by secretaries. We had terrified waitresses with questions about Fidel’s penis.

Then we hit pay dirt. In Sancti Spiritus, we arranged to stay at a private home owned by a nice elderly woman and her handsome, flamboyantly gay son, Gigi, who spoke perfect English. We saw a potential in. Gigi admired Wes, and he admired my sunglasses. He asked if he could borrow them, and he wore them out one night. The next morning when an obviously hungover Gigi explained that he had lost my sunglasses, we leaped for the jugular.


An hour later, we found ourselves in the atrium of a colonial mansion owned by a very small woman named Yeny and her husband, Arnold. Gigi had spoken to Yeny after we had told him about our story, and she invited the three of us over. Yeny had shoulder-length red hair, sunken cheeks, and very large front teeth. We are sorry to say that she resembled a worn-out donkey.

As we spoke with Yeny in the atrium, Arnold sat with his back to us in an adjacent den lined with aluminum bookcases. The books were shelved backward, with their spines facing the wall so that their titles were a mystery. Arnold was a good-looking older man shaped like a gorilla. He wore carpenter jeans and no shirt, and sat before a delicate antique secretary so small it barely held his typewriter.

With great enthusiasm, Yeny asked us if we would like a tour. Of course we said yes. When we got to the dining room she pointed at the floor and in pidgin English said, “On these very tiles.” She looked over her shoulder at her husband, still sitting with his back to us. Then she leaned in close to us and whispered, “Fidel.”

Just then her husband looked up. “Coffee?” he asked.

“Do you have time for lunch?” Wes said. “We’d like to take you to lunch.” Arnold smiled and shook his head no.

“Good idea,” Gigi said, seizing the opportunity by making Yeny’s decision for her. “I will take you to my friend’s restaurant.”

By her fourth daiquiri, Yeny was giving it all up in vulgar detail. “Chocolate!” she said, her eyes widening in fond remembrance. Gigi translated, but we could tell he was embarrassed and wasn’t telling us everything she said. Still, it was pretty damn hot.


“He fed me pastries from a place in Paris. I don’t remember the name, but he was always bragging about the pastries. They were delicious. He would pour chocolate all over me.

“Those were the happiest days of my life. I always asked him if he wanted other women to join us. But he said no man should make love to more than one woman at a time. He didn’t like orgies. He never would have other men in the room when he was making love to me. But sometimes he would let other women watch us. He would tell them to eat the pastries!

“With Fidel, it was about pleasure, you see. It’s true that he preferred other men’s wives. So the men think he wanted to cuckold them. They thought it was power. Or making other men raise his children. Actually he was very kind. He did not like to break a woman’s spirit. He said unmarried women fell too much in love. Some women… could never forget ‘Alejandro.’ They had problems.” (A reference to Alexander the Great, “Alejandro” became Fidel’s nom de guerre during the revolution.)

Gigi looked very nervous. He tried to interrupt, but Yeny told him to shut up.

“I still love him,” she said. “Those days are sacred to me. In my life I loved two men, my husband and Fidel. He is dying now. The greatest man the world has ever known.

“Arnold called him the ‘cuckoo bird’ behind his back because of all those children. But no, he preferred married women because he knows we are better in bed, and he would never sleep with a prostitute. Thousands of women, and he never touched a prostitute. This is something most people don’t know. I tell you a secret. It was because of Che. Che was an ass. Nobody will admit it."


“Che caught him once with a prostitute, when they were young men, and he scolded him. Che scolding Fidel. Think of it. Ridiculous! So many times I said, ‘Why don’t you send him home? The prick.’ He explained that it was against morality. To treat a woman like an object. That was when Fidel became a lover. I don’t know why the pastries. And of course the cigars. I think that was why your President Clinton had the cigar thing. He was imitating Fidel. All men, secretly, they want to be Fidel.”

The waiter brought her fifth drink. Gigi put his hand over the glass, and Yeny immediately slapped it away. She spoke to him very rapidly in Spanish.

After she finished, Gigi said, “I can’t repeat that.”

“Please?” we said. “This is great stuff.”

“No. I mean, I don’t understand what’s she’s saying. She’s too drunk.”

Yeny took Holly by the wrist.

“If he asks you… You must.”

“It’s fine. You have my permission,” the driver said.

About a week after our lunch with Yeny, we were sitting in an immaculate leather-seated emerald 1950s Corvair convertible, on our way to the beach.

“What do you mean, we have your permission?” Holly asked.

The driver shrugged and laughed.

“This is your car, right?” Wes said. “There are no microphones in your car. We’ve got the top down, nobody can hear us.”

The driver smiled and shrugged.

“We thought it was OK to ask about his love life,” Wes said. “Our friend told us that. Two friends. He had 35,000 lovers.”


The driver rolled his eyes. “Two hundred thousand. Two million…” He was on a roll, his voice thick with sarcasm. “My aunt, she slept with Fidel. My grandmother, she slept with Fidel. My uncle, he slept with Fidel. You know, we have all slept with Fidel. Fidel and I made love in this car.”

He made a face at us. Neither of us knew what he really meant.

“But seriously, does Fidel sleep with men?” Wes asked, pointing out that Cuba is one of the most gay-friendly countries in the world. Free sex-change operations have been provided by the government since 2010, and legislation that would allow same-sex marriages is currently pending.

Our driver ignored the question. He said, “I have seven different cousins named Fidelito [the name of Castro’s firstborn son]. Any bastard, always Fidelito… Fidelito. Fidelito. If a woman gets pregnant, and she won’t name the father…”

He came to his senses a bit. He turned to Wes, “So, my friend. You are American?”

“Canadian,” Wes answered.

“What kind of cigar do you like to smoke?”


“It’s a special this week,” the driver said. “Last day. I have.”

Wes bought a case from him.

Names and other identifying details have been changed to protect subjects’ identities.