Cigar Aficionado

In the summer of 1956, Errol Flynn traveled to Havana to star in The Big Boodle, a low-grade crime drama about a casino croupier who stumbles across a counterfeiting ring. It was a far cry from the big-budget, high-flying epics that had made Flynn a star 20 years earlier, but, then, the 47-year-old was no longer the dashing swashbuckler. "He was semi-retired," recalls Guillermo Alvarez Guedes, at the time a young Cuban television actor cast in the film. "He was up to something like 300 pounds, from not working. I heard he went to Brazil to get ready for the role."

If he did, the regimen didn't take. When Flynn showed up on the set—the casino interiors were filmed at the famed Hotel Nacional—he was overweight, drinking heavily and had trouble ing his lines. Nevertheless, Flynn continued to exude a certain aura. "He was the prototype of the Hollywood star," says Alvarez Guedes, who today is a well-known comedian and radio personality in Miami. "He was very adept at causing a commotion and grabbing the headlines."

Since the mid-1930s, Flynn had been one of Hollywood's highest earners, one of its most renowned bons vivants and its most notorious star. But in many ways, his most intriguing role still lay ahead. In Cuba, a couple years after making The Big Boodle, Flynn would become involved in a burgeoning revolution, playing opposite a new kind of international star, one not confined to the screen: Fidel Castro. It would prove to be a most memorable experience, even for a man whose life had been one long series of improbable exploits.

Born in the Australian territory of Tasmania in 1909, the preternaturally handsome Flynn had come to Hollywood almost by chance. After trying his hand at a number of jobs, including plantation overseer, gold prospector and even correspondent for The Sydney Bulletin, he had drifted into acting. When a Warner Bros. talent agent spotted him doing bit parts in its English studio films in 1934 (following a stint with a British repertory company), he signed the 25-year-old to a modest contract of $150 a week.

Once in Hollywood, Flynn didn't have to wait long for his big break. In 1935, he was cast as the lead in Captain Blood, the tale of an eighteenth-century Irish doctor forced to become a pirate. It became one of the year's most popular films and it cemented a partnership between Flynn, director Michael Curtiz and costar Olivia de Havilland that would last for the next five years and produce such classic action films as The Charge of the Light Brigade, The Adventures of Robin Hood and Santa Fe Trail. (The excitement on-screen apparently spilled over onto the studio lot: Flynn and the tyrannical Curtiz clashed violently and often, while Flynn and de Havilland are rumored to have carried on a long-running affair.)

Playing a succession of larger-than-life heroes—not only Robin Hood, but Indian fighter George Custer, nineteenth-century heavyweight boxing champion Jim Corbett and legendary lover Don Juan—Flynn became something of one himself. Blessed with an athlete's natural grace and a rogue's charm, he was a compelling screen presence and, perhaps to a greater degree than any of his contemporaries, the era's cinematic ideal of what a man should be.

It was a status that turned out to be both a blessing and a burden. A well-publicized statutory rape trial in 1942, in which Flynn was charged with having sex with two different underage girls on different occasions, cast a harsh light on his private life. Movie fans discovered what Hollywood insiders had long known: despite his marriage to actress Lili Damita, Flynn essentially lived the life of a bachelor, one with a predilection for young girls. "He liked to teach women and women liked to learn from him," says daughter Rory Flynn, the product of the actor's marriage to second wife Nora Eddington. "He was a man who never had to chase women, and who would never say no. He would never deny himself." Or, as Flynn himself once put it: "If you meet a young lady who, in fact, invites herself for a trip on your yacht...knowing in advance full well what the risks are, who the hell asks her for her birth certificate, especially when she is built like Venus?"

Though Flynn was acquitted of the charges, the trial was a humiliating experience for him. Most regrettable, he believed, was the famous phrase it spawned: "In like Flynn." A pointed reference to the movie star's easy way with the ladies, it remains a familiar expression to this day, even if few people know its origin.

The rape trial, for all the negative press it generated, did little to diminish Flynn's appeal at the box office. More damaging to his career was the postwar shift in Hollywood films, away from costume dramas and toward gritty, contemporary urban storylines with psychologically complex characters. It was a cultural sea change that largely relegated Flynn to second-tier stardom. In 1952, he and Warners parted ways.

For the next few years Flynn produced and starred in European films and even took work in television—at the time, a fledgling medium that few screen stars would deign to grace. "He went around hustling for money," his daughter says, "but he was drinking. Nobody would touch him." With his finances in disarray—to go along with his professional woes and years of reckless spending, he discovered his business manager had been stealing from him—Flynn was probably only too happy to pack his bags for Havana in May 1956.

The Big Boodle, produced by tiny Monteflor Inc. and released through United Artists, did little for Flynn's sagging career, but it did bring him to Cuba at a critical time in his life—and in the island's history. Fidel Castro, the 29-year-old resistance leader living in exile in Mexico, had declared that 1956 would be a year of reckoning for Cuban dictator Fulgencio Batista. Though the prediction would prove premature, by year's end Castro was indeed back in Cuba, hiding out in the mountains of Oriente province and solidifying his ragtag fighting force.

Flynn, if he had not heard of Castro previously, surely would have become familiar with the name that summer, when Havana was abuzz with the young rebel's rumored return, or, at the very least, by early 1957, when New York Times reporter Herbert Matthews wrote a series of lengthy articles identifying Castro as "the most dangerous enemy General Batista has yet faced." Not that Flynn was looking for a revolution. A frequent visitor to Havana since the 1930s, Hollywood's most famous swashbuckler was both an avid gambler and a habitué of the city's flesh dens. "I enter a whorehouse with the same interest as I do the British Museum or the Metropolitan—in the same spirit of curiosity," he once confessed. Cuba, under the dual istration of Batista and mob boss Meyer Lansky, was a paradise for dissolute tourists, one practically built with Flynn in mind.

And yet, by the late 1950s, the actor found himself drawn more and more to the revolution and its charismatic leader. "The one thing [Flynn] was for was freedom," says daughter Rory, offering one possible explanation for the attraction. But surely there was more to it than that. Might Flynn not have seen in Castro the reflection of his own, younger swashbuckling self—a real-life Robin Hood, complete with his own band of merry men?

Or, perhaps, he saw an opportunity to relive his own celluloid adventures. As he wrote in his autobiography, My Wicked, Wicked Ways, living up to his image as the quintessential man of action became almost an obsession for him: "There was a fellow inside myself who would say to me, 'You are an impostor, Flynn. In real life you don't do any of the things you do on the screen. You are no more capable of that kind of action in real life than a choirboy.' Maybe that is why, in my private life, I went ahead, consciously or unconsciously, to live such a life of reality instead of just portraying it all the time."

Most memorably, he had traveled to Spain as a correspondent for the Hearst newspaper chain in 1937, to cover the civil war. In a dispatch that must have sent shivers through the Warner Bros. offices, on April 5 The New York Times reported that Flynn had "received a minor bullet wound on his face." In truth, he had been nicked by some flying debris. Still, he had been close enough to the action for that to have been a hazard.

Given this history, and the increasing public fascination with Castro, it should have come as a surprise to no one when Flynn returned to Cuba in late 1958, again in the employ of the Hearst press. He arrived in Havana in late December, accompanied by his teenage girlfriend, Beverly Aadland. According to biographer Jeffrey Meyers, who recounts the episode in his book, Inherited Risk, Flynn had a secret meeting with a Castro agent at the Hotel Nacional. It was just before midnight on December 25. Two days later, after two plane flights and a harrowing car trip through the dirt roads of Oriente, Flynn met face-to-face with Castro. Impressed by the rebel leader, Flynn interviewed him extensively on his hopes for the future. One of Castro's men, though, had a question for the former screen star in their midst: "How come you look so young in the movies and so old now?"

Flynn and Castro spent the next five days together, observing the fighting around the city of Santiago. As in Spain 20 years earlier, a minor wound suffered by Flynn, a shell fragment in his shin, was blown up into something much more dramatic by the press: the loss of a leg. Limbs intact, Flynn not only managed to file his dispatches, but he was the only American correspondent with Castro when Batista fled the country on New Year's Day 1959.

A week later, when Castro arrived in Havana, Flynn was again close by. Legendary screenwriter Budd Schulberg (On the Waterfront), who had traveled to Cuba to observe Castro's triumph, and who a decade later would write a novel, Sanctuary V, based loosely on what he saw, re that it was Flynn who helped him secure an audience with the world's most famous revolutionary. "I met Castro in the lobby of a Havana hotel, arm in arm with Errol Flynn, who I knew from Hollywood," Schulberg told an interviewer in 2005. "So I went up to the room with them—Errol served up a tall vodka—and got to talk to Castro. The whole world wanted to talk to him."

However much Flynn might have appeared to enjoy his status as Castro's most visible American er, there was a dark side to the role as well. British explorer Robin Hanbury-Tenison, who, like Schulberg, was drawn to Cuba by the import of the historical moment and spent time with Flynn there, once recalled the unique strain the actor was under: "Errol was observing the downside of revolution at close quarters. As an international figure, he was useful to the regime, lending some legitimacy to the nastier things they felt had to be done to secure their hold on the country. Quick trials, kangaroo courts, followed by executions took place every evening. Errol was expected to attend."

That same January, Flynn appeared as a guest on the popular Canadian news/quiz program "Front Page Challenge." Addressing rumors that he had participated in some of the rebel fighting, he assured the of interviewers that he hadn't "[picked] up anything more dangerous than a ballpoint pen." It was a good line and it gave everybody a laugh. His attempt to sidestep the issue of Castro's bloody reprisals, however, was not nearly as successful. "I know that [Castro] himself and his brother, Raúl, and his little old lady mother, who's a doll, she really is," Flynn stammered, "don't believe in retribution... uh, summary retribution." His half-hearted assurances aside, he was disillusioned by what he had seen, and in time would conclude that the revolution he had ed so enthusiastically was not so different from the government it had replaced.

American media reaction to Flynn's Cuban adventure was predictably snide. Time magazine, visiting with him in his Manhattan home, described him as "agog with glory after his fast tour as a 'freelance newsman,'" sarcastically adding that he kept "scribbled notebooks full of tidbits for a biography of Hero Fidel." The writer even took a jab at Flynn's decorating, noting the apartment's fuchsia and pink "Disneylandish bar."

Flynn had simply been a joke for too long to be taken seriously now. Of course, Flynn's own behavior, real or reputed, had encouraged some of the barbs. Alvarez Guedes still recalls hearing a story involving his old costar's pilgrimage to see Castro. "[Flynn] went up to the Sierra Maestra [the mountain range where the rebels had their base of operations], wearing officer's stripes," says the 80-year-old comedian, clearly enjoying the tale. "Fidel found out and took them off. 'This is not Hollywood,' he told him. 'This is a revolution!'"

If Flynn had been guilty of combining play-acting with his journalistic duties, the line between fact and fiction would be blurred beyond recognition when he returned to Cuba in the spring of 1959. Still deep in debt, Flynn set out to capitalize on his association with Castro—or perhaps just create a tax write-off—by making Cuban Rebel Girls, a low-budget exploitation film that promised to tell the story of the Cuban struggle "straight from behind rebel lines." It would star Flynn as himself (as a war correspondent) and the 17-year-old Aadland as an American who s the fight.

Flynn's partner in the enterprise was Barry Mahon, yet another of those heroic, colorful figures Flynn seemed to forever be seeking out. Mahon had been a Second World War flying ace whose exploits in a German prisoner of war camp reportedly inspired the Steve McQueen character in The Great Escape. He and Flynn had met in the early 1950s, when Mahon, who had heard that Flynn liked adventure and was having money troubles, approached the actor about making a film in Europe. "My father wrangled a meeting with Errol Flynn at 10 in the morning," says Doris Keating, Mahon's daughter. "They started drinking Screwdrivers [and] talking about the war. At three that afternoon, Flynn's agent called up wanting to renew his contract. Flynn told him he should talk to his new manager and handed my father the phone."

Flynn and Mahon cemented their vodka-fueled friendship and, after securing some backing from United Artists, traveled to Italy to film Crossed Swords. The film, directed by screenwriter Milton Krims, was a historical epic intended to remind audiences of Flynn's earlier glories, but, in the end, not even sex siren Gina Lollobrigida as a damsel in distress could save the project. Indeed, the biggest winner might have been an actor and director who had nothing to do with the film. "Orson Welles [who was then living in Europe] would come and hang around the set," says Keating. "He married an actress [Paola Mori] who played a lady-in-waiting."

For their next European production, The Story of William Tell, Flynn and Mahon built an elaborate set in the Italian Alps. The film was never completed. "They ran out of money," explains Keating, who in the 1980s produced a television movie about Flynn's life. "The [Italian] government came and took all of my mother's furs, her jewelry." They also seized Flynn's two cars, along with third wife Patrice Wymore's clothes. "They weren't businessmen," says Keating of her father and Flynn. "They were real cavalier guys, borrowing from Peter to pay Paul."

The debacle only deepened Flynn's financial and personal crises. He and Mahon agreed to go their separate ways in 1954, but not before discovering they had something other than a lack of financial acumen in common. "They both got hepatitis," recalls Keating. "But Flynn kept drinking." And not only drinking. The actor, who had long experimented with drugs, was developing an addiction to morphine.

By 1959, when he and Mahon reunited in Cuba, Flynn wasn't simply out of shape. He was bloated, a hopelessly corrupted version of the handsome idol he had once been. And he was dying. "I'm sick, Uncle," he told his old friend, director Raoul Walsh. "My lungs have had it and the quacks say my liver is shot to hell. So what does it matter where I die?"

Cuban Rebel Girls doesn't appear to have required much from the ailing Flynn. The film was a mixture of staid reenactments and footage of rebel fighting shot the previous year. Flynn, though he appears in a few scenes—including one that re-creates his secret meeting with the Castro agent in Havana—has few spoken lines. Rather, his chief contribution is as narrator. Aadland plays a young American brought into the struggle through an old friend who has gone to Cuba as a soldier of fortune. Aside from its vaguely naughty title, the film had little to offer and was savaged by critics upon its release at the end of 1959. "With some additional experience," wrote The New York Times reviewer, "[the other actors] and Miss Aadland could qualify as amateurs. Mr. Flynn cannot be blamed for giving the appearance of being very, very tired throughout these phlegmatic proceedings."

Perhaps because he feared for his safety—FBI reports from the time note that Flynn was harshly questioned by Cuban secret police upon his return to the island in 1959—or maybe because his pride wouldn't allow him to publicly it how wrong he had been, the actor participated in one last homage to the revolution. He filmed an introduction to independent producer Victor Pahlen's celebratory semi-documentary on the rise of Castro, Cuban Story. (The film, originally titled The Truth About Fidel Castro Revolution, was shown in Moscow in the early 1960s and not seen again until its rediscovery in 2001.)

Only a few months after his final Cuba trip, on October 14, 1959, Flynn suffered a fatal heart attack in Vancouver. He had gone there with Aadland to sell his beloved yacht, the Zaca, to a Canadian businessman before the IRS could put a lien on it. It was an ignominious exit for a star who, at his height, had been as big as Gable, Bogart or Cooper.

But then, that's probably not the way Flynn would have chosen to be ed. "I think he felt his films were the least interesting part of his life," says Rory Flynn, now 60 and living in Los Angeles. "Cuba was a happy ending. He was in the middle of a revolution, tramping through the hills with a beautiful girl." And, of course, he got to be Errol Flynn—one last time.

Gaspar González is a Miami-based writer and filmmaker.