Could the End of the Embargo Kill the Cuban-Cigar Industry?


“When did you last travel to Cuba?” the man demanded. “And when was the last time before that? And before that?”

The questions cut through the decades. The room was bigger now. The windows were no longer barred. Men in suits had replaced soldiers in fatigues. And the crackle of firing squads had faded into history.

But for José “Pepe” Montagne, the interrogation echoed back to 1964. Back to when he was a baby. Back to when it was his father — not he — being hounded by Fidel Castro’s henchmen.

“Are you a member of any organizations of Cuban-Americans?” the man in the suit continued. “Would you welcome the overthrow of the present Cuban government by force?”

Forty-one years after imprisoning his father, the Cuban government had now come for Pepe. In a law office high above Coral Gables, Florida, Castro’s attorneys grilled him not about democracy or freedom of speech or civil rights, but about something even more dangerous for the revolution: cigars.


“Would you agree that Cuban cigars are generally known to be of high quality?” one of the lawyers asked.

“Not at this time,” Pepe shot back.

“So they were at some point in time?”

“They had relevance,” Pepe said. “I’m thinking about pre-Castro Cuba.”

For the next six hours, the attorneys would probe Pepe about tobacco varietals and trademark law. Habanos S.A., the Cuban government’s state-owned cigar company, was suing Pepe in U.S. federal court. His offense? Calling his cigars “Guantanamera” — a name Cuba claimed and now wanted to slap on its own stogies.

That was 2005. Ten years later, Pepe is still battling the communist country in court. He’s not alone. Over the past decade, the Cuban government has gone after scores of American cigar makers and vendors — most of them Cuban exiles living in South Florida. For local tabacaleros, these legal battles add fresh insult to old injuries. Many fled Cuba at gunpoint, only to find themselves dragged to American court by a country still on the list of state sponsors of terror.

This is the first of a two-part series. Read part two, “Cigar Wars.”

Now, as most of America looks forward to the imminent fall of the embargo as an opportunity to visit the island or smoke a stogy, Miami’s Cuban cigar makers fear what might happen next. Chased out of Cuba as Castro took over their tobacco fields, many refounded their companies in America. Some, like legendary cigar maestro José Padrón, have risen to the top of the trade. Keeping Cuban cigars out of the States enabled these exiles to thrive in South Florida, arguably the capital of America’s cigar industry. But in recent years, as the embargo has begun to teeter, the Cuban government has gone after its competitors in preparation for the day when its products can finally invade El Imperio.

With President Barack Obama now pushing to restore ties between the embittered rivals, Cuban-American cigar makers have the most to lose. Pepe, for one, could soon find himself out of business, buried under a wave of new lawsuits and cheap Cuban cigars.

This trademark tussle is just the tip of the pilón when it comes to trouble in the tobacco industry. There are $100 million wrongful-death lawsuits, $50 billion hostile corporate takeovers, smuggled tobacco seeds, and suspicions that Cuba is already secretly circumventing the embargo with its cigars.

The end of the embargo will have an impact far beyond tobacco, of course. When Congress finally repeals the 55-year-old blockade, Americans will flood the island with dollars and ideas about democracy. Whether this will lead to regime change or retrenchment is as hazy as a Havana smoking parlor.

But cigars will be at the center of it all. More than a half-century after Fidel and Che Guevara swept down from the Sierra Maestra with puros perched on their lips, cigars remain crucial to Cuba. They are one of the country’s biggest exports, a rare growth industry in the socialist state. They are also a powerful symbol of the country and its storied history. Cuba may be a tiny tropical island, but in the multibillion-dollar cigar industry, it is still a titan.

To explore what cigars and the waning embargo mean for both Cuba and the United States, we dived into court records, interviewed experts, traveled to Nicaragua, and smoked enough stogies to slay a bear. In part one of a two-part series, we tell the tales of Pepe, Padrón, and their predecessors — the backstory of a global industry on the brink of massive change.

“Nobody knows what is going to happen next,” says Pepe, who, with his shock of white hair and ever-present cigar, bears a striking resemblance to Hannibal from The A-Team.

“This is more than my business. It’s my passion, my life,” he says. “I’m fighting against an entire country! It’s like a housecat trying to fend off a hungry lion.”

The history of Cuba is one of tobacco and turmoil. Like tendrils of smoke, cigars wind their way through the country’s troubled past. From Christopher Columbus to Fidel Castro, the island’s bloody story can be wrapped inside leaves of Nicotiana tabacum. And as fruit of the island’s rich soil, cigars symbolize not only the nation’s promise but also its painful decline.

When Columbus weighed anchor off Cuba on October 28, 1492, his landing party was greeted by tobacco-toting Taíno Indians. The natives walked around “with a lighted brand made of a kind of plant whose aroma it was their custom to inhale,” sixteenth-century historian Bartolomé de las Casas later wrote. It didn’t take long for Columbus’s crew to begin smoking the tobacco-stuffed plantain leaves themselves.

Indigenous people across the Americas had consumed tobacco for centuries. Warao shamans inhaled nearly lethal doses of tobacco dust before embarking on perilous trails through the jaguar-prowled Amazon. In Colombia, Aguarana shamans shielded themselves from similar dangers via tobacco enemas, Iain Gately wrote in his 2001 book, Tobacco: A Cultural History of How an Exotic Plant Seduced Civilization. Some tribes smoked cigars so large they had to be held up with special sticks. Mayan nobles smoked stogies while praying to their bloodthirsty god. And Aztecs mixed tobacco with pulverized rabbits and fox excrement as a cure for gout and blew smoke over warriors before they headed into battle.

Cuba, in particular, seemed predestined to play a special role in the spread of tobacco. Columbus took leaves from the island to Europe, where tobacco would eventually become a craze. At first, however, Europeans looked down on the strange, smokable weed. Spanish men suffering from syphilis — another New World export — smoked to ease their pain, so tobacco became linked with sin, Gately wrote. It didn’t help that the sight and smell of smoke was already associated with the Devil.

Sin was in strong demand in Europe, however, and within a century, tobacco had taken root across the Atlantic. Spain turned Cuba into its chief tobacco colony, shipping the precious cargo across the ocean to Seville, where scantily clad women — memorialized in the opera Carmen — rolled tobacco leaves into cigars.

In 1817, Spain relaxed controls on its colony, and Cuba’s cigar industry took off. Soon, puros produced in Havana were pouring into the island’s newly founded northern neighbor: the United States. By 1855, Cuba boasted 9,500 tobacco plantations and more than 15,000 tobacco workers, according to Gately. Tobacco was the colony’s largest crop.

As Cubans increasingly resented Spain, the islanders drifted closer to the United States. Both tobacco and dissidents began to flow into South Florida. Cuban revolutionary José Martí toured cigar factories in Key West and Ybor City, delivering impassioned speeches and raising funds for revolt. And when the order was finally given in 1895, it was supposedly smuggled into Cuba inside a cigar.

The United States entered the war against Spain three years later, after the sinking of the U.S.S. Maine. The U.S. probably would have taken Cuba as its own tobacco outpost — a plot hatched by Thomas Jefferson a century earlier — if not for the Teller Amendment, which barred America from annexing the island. Even still, the majority of Cuba’s cigar factories were soon owned by gringos.

The American appetite for Cuban tobacco grew during the twentieth century. Soldiers became hooked on cigarettes during World Wars I and II, and inequality on the island ensured that Cuban cigars remained affordable in the States.

The Cuban revolution, however, altered not only the country’s history but also the global cigar industry. When Fidel Castro and his guerrillas took control of the capital on New Year’s Day 1959, many cigar makers fled the country. Others lost their factories or plantations to the revolution’s increasingly radical policies. Private farms became cooperatives, and production was centralized in a few large factories.

Many Cuban cigar makers moved their operations to the city of Santiago in the Dominican Republic. From there, they were forced to compete against their own brands, now under socialist control in Cuba. Smokers in Europe were confounded by cigars bearing identical names — Partagás, Romeo y Julieta, Punch — but hailing from different countries.

The embargo prevented any similar confusion in the United States. Castro had visited the U.S. shortly after taking power and even met with Vice President Richard Nixon. But as Cuba nationalized key industries, the States began imposing trade sanctions. By 1960, the U.S. had stopped buying Cuban sugar and cut off oil shipments to the island, forcing Cuba to turn to the Soviets.

Finally, on February 7, 1962, President John F. Kennedy signed a decree banning all Cuban products from being imported into the U.S. (but not before receiving one final shipment of his favorite Petit Upmanns).

Castro, also an avid cigar smoker, retaliated by hoarding some of Cuba’s finest tobacco. In the mid-1960s, Fidel recruited local farmers in the Vuelta Abajo region to found Cohiba, a line of richly fermented cigars supplied exclusively to Cuban government officials.

The CIA then spent the next decade lacing Cohibas with various poisons and explosives. Yet El Comandante never went near the sabotaged cigars. And when an ideal opportunity to smoke out the strongman finally arose, the incident exploded — but not the way the spy agency wanted.


“I hear you make a good cigar
over there in Miami,”
Castro said. “May I try one?”

José Orlando Padrón stirred uneasily. Seventeen years earlier, he had fled Cuba as Castro pushed the country toward communism. Now the Miami cigar maker was sitting across from his persecutor in a Havana courtyard. As one of the first exiles to return to the island since the revolution, Padrón was on a mission to negotiate the release of almost 4,000 political prisoners. Castro, however, was intent on talking tobacco.

Dressed in his traditional olive fatigues, Castro had immediately spotted the cigars peeking out of Padrón’s suit pocket. Journalists had yet to arrive at the meeting, so Padrón thought nothing of handing over a stogy and sparking one up for himself.

“It’s good,” Castro said with a grin as he exhaled the pungent smoke. A few minutes later, however, El Comandante asked to see another. This time, a photographer was on hand to snap the exchange. “Fidel Castro smokes Padrón cigars,” read the caption in newspapers around the world.

Padrón returned to Miami with the political prisoners, but his problems were just beginning. Cuban-American radicals accused him of cozying up to a dictator and welcomed him back with a bang. Four times his Little Havana factory was bombed. His warehouses in Nicaragua were torched, and he was nearly kidnapped.

More than anyone else’s story, Padrón’s tale encapsulates the insane world of Cuban cigars. It’s an industry in which politics and power are blended like tobacco leaves and then hidden beneath a pretty wrapper. For Padrón, the pursuit of the perfect puro has taken him to four countries, through civil wars, and around economic blockades.

But even the grandfather of Cuban cigars isn’t sure what will happen when the embargo falls and his homeland opens again.

“We Cubans are caught between two fires,” says Padrón, now 88 years old. “One over there and another one here.”

Padrón grew up in Pinar del Río, a region 100 miles west of Havana famous for its rich soil and succulent tobacco. His father owned a 250-acre farm, much of which he rented out to sharecroppers.

Despite his father’s landholdings, Padrón’s earliest memories were glimpses of poverty. By the time he was old enough to help in the fields, the Great Depression had decimated the demand for tobacco. As its price plummeted, Padrón’s father took to slaughtering a cow each week just so his sharecroppers could survive. “We had barbecued beef and rice that we grew ourselves,” he says. “The workers ate like beasts.”

Luckily, the war arrived before the cattle ran out. And with each cigarette that a European or Yankee soldier smoked, the price of tobacco in Cuba rose just a little. From 1942 to 1943, the crop’s value nearly doubled. Cuban farmers scrambled to plant as many seeds as possible, driving down its quality, so Padrón’s father helped found the Association of the Tobacco Growers of Cuba to stabilize the market.

For more than a decade, Cuba’s cigar industry grew steadily. But as Castro’s band of guerrillas battled their way west across the island, uncertainty spread in the industry. Dictator Fulgencio Batista fled New Year’s Day 1959, and Castro quickly set about nationalizing industries and redistributing farmland. The Padróns were stripped of their tobacco farms, some of which were used to raise geese for the government.

José Padrón had initially welcomed the revolution, even taking up arms at one point to assist in the fight. But now he vowed to leave the island. On April Fools’ Day 1961, he finally found a spot on a plane to Spain. The date was fitting: It seemed like a cruel joke the way his life had fallen apart, from losing his family’s business to getting divorced and leaving his two children behind.

“It was a bitch to get out of Cuba,” he says. “When I caught the plane, I felt free because I could see what was coming. Thank God they didn’t execute me first, because many of my friends were shot or thrown in prison.”

Padrón landed in Spain penniless. He asked for asylum but, like thousands of other Cubans, had to endure months of embarrassment and hunger in his adopted country. “I went wherever I saw signs for ropa vieja,” he says. After eight months, he decided to ditch Spain for America. He took a train to Vigo and boarded the cruise ship Covadonga, bound for New York City.

The Big Apple wasn’t much better than Spain. Padrón stayed in a friend’s tiny apartment. “I couldn’t move!” he says. “I had to go to the lobby just to put on my shoes.” He made a dollar per hour ironing men’s suits. Then he worked the graveyard shift stocking airplanes with supplies for Europe.

In February 1962, almost a year after fleeing Cuba, Padrón arrived in Miami, where the sun blazed the same as it had back in Pinar del Río and Cubans were everywhere. Padrón rented a roach-infested room and received $62 a month in refugee funds.

After two months on the dole, however, Padrón felt like a freeloader. So he took out a loan, bought some carpentry equipment, and began doing odd jobs for $100 a week. But in his mind, he was building more than cabinets and kitchenettes. Padrón was already assembling his own tobacco factory.

His reasoning was simple: “I couldn’t find a damn thing to smoke here!” he says. “There were some little Filipino cigars that cost 10 cents but didn’t taste like anything. So I said to myself: ‘I’m going to build myself a factory so at least I’ll have something to smoke!’ ”

Despite the steady stream of Cubans, there was only one other cigar maker in town at that time. By 1964, Padrón had cobbled together enough money to rent a warehouse on Flagler Street. He hired a single tobacco roller and imported leaves from Brazil, Puerto Rico, and Connecticut. Gringos and cubanos alike snapped up the smokes, and soon Padrón was selling several million cigars a year.

But Padrón’s fortune — and that of Cuban cigars — would take another strange turn with the appearance of a mysterious visitor. In 1967, a man stopped by Padrón’s factory with an odd request. He was on his way to Europe to try to sell some tobacco. Would Don Orlando take a look at his product?

In a spare hotel room on Biscayne Boulevard, the unidentified man opened his luggage and showed Padrón some of the most beautiful tobacco leaves he had ever seen. “Where did you get these?” Padrón asked.

“From Nicaragua,” the man answered. Padrón told him that he didn’t think Europeans would be interested in the tobacco — it was too robust for their taste. His own curiosity was piqued, however. A few months later, the man passed through Miami on his way back to Nicaragua. Sure enough, no one in Europe took a gamble on the potent tobacco. But Padrón agreed to travel to Nicaragua to see the farms for himself.

That’s when the mysterious man told Padrón whom he was working for: Anastasio Somoza, the recently elected president of Nicaragua and son of the dictator of the same name. Padrón flew to Nicaragua and took a jeep to Jalapa, where the president had been conducting a grand tobacco experiment. Legend had it that tobacco was grown in the region before the conquistadors arrived. Now Somoza was sowing Cuban seeds in the fertile volcanic earth to see if he could boost the Central American country’s struggling economy.

“Somoza was waiting for me at the farm,” Padrón recalls. “I told him: ‘This is the second Cuba. This soil doesn’t exist anywhere else.’ That’s how things began.”

Padrón started buying the tobacco and importing it to Miami. Three years later, he opened his own factory in the northern Nicaraguan city of Estelí. It was only the second factory in what would soon become a bustling tobacco town. “People call me the Christopher Columbus of Nicaragua,” he says with a laugh.

Nicaragua’s rich tobacco would help make Padrón famous, but the move to Central America would also nearly kill him. In 1972, a massive earthquake hit the nearby capital of Managua, killing more than 6,000 people. One hundred miles north in Estelí, Padrón’s factory shook but remained standing.

Throughout the 1970s, Padrón’s business boomed in Nicaragua. But, as in Cuba, the country was gradually being torn apart by broader forces. Somoza grew increasingly despotic, ordering his soldiers to kidnap and kill political opponents, student activists, and journalists. By 1975, parts of the country were in open rebellion. On January 10, 1978, Somoza orchestrated the murder of Pedro Joaquín Chamorro, the popular editor of an opposition newspaper. The country broke out into full-on civil war.

Estelí was a hotbed of support for the socialist Sandinistas, led by Daniel Ortega. Riots ravaged the city, and Padrón’s cigar factory burned down May 24, 1978.

On October 20 that year, Padrón headed to Havana to arrange the release of 3,600 political prisoners. (Fidel might not have been the only one interested in talking about tobacco. Many people believe Padrón asked El Comandante to tell Ortega to spare his tobacco operations in Estelí. Padrón denies making the request.)

Miami’s more radical Cuban immigrants had already suspected Padrón of sitting down with Fidel. But after the Miami Herald published a front-page photo of Castro sucking on one of Padrón’s stogies, the cigar maker found himself a target of hate.

Five times over the next four years, the Padrón cigar factory was attacked. The first time, a bomb left in a dumpster failed to detonate. Padrón’s own nephew disarmed the device. The next four bombs, however, exploded, scorching walls and shattering windows. Amazingly, no one was ever hurt. But the Padrón family was terrified. Across the nation, people suspected of sympathizing with the Cuban regime were being killed. In New Jersey, stores that shipped food to the island were firebombed. In New York, Cuba’s mission to the United Nations was attacked.

No place was more volatile than Miami, however. The radical dissident group Omega 7 single-handedly claimed responsibility for scores of bombings in the Magic City. Padrón began packing a pistol underneath his clothes. He also installed a remote-controlled starter on his car to avoid falling prey to the car bombs that had claimed several Cubans living in Miami.

But the bombings backfired. Padrón’s business kept climbing.

“Sales went way up!” Padrón says. “I went to Cuba to get my friends out of prison…Afterwards came all the problems with the bombs and everything — all because Fidel asked me for a cigar. But he asked me!”

Things remained volatile in Nicaragua as well. Padrón’s factory there was attacked several more times, once by arson and another by vandals who had spray-painted “Padrón traitor” on its yellow walls.

However, the biggest blow to business wasn’t the civil war, but another embargo. In 1985, President Ronald Reagan imposed a blockade on all Nicaraguan goods, calling the Sandinistas “an unusual and extraordinary threat.” The embargo — which was later ruled illegal by an international court — was complemented by the millions of dollars Reagan sent to the Contras, militias secretly trained by America to overthrow the Sandinistas.

The embargo forced Padrón to shift production to Honduras for nearly five years. While in Danlí, a town near the border with Nicaragua, Padrón was the target of an elaborate kidnapping plot. One night, he received a phone call from a woman he had never met. “Don Orlando, I must come and see you,” she said.

The next day, the woman arrived at the Padrón factory with a bag full of documents. Two men had gotten drunk and left the bag on a bus by mistake, she said. Inside the bag were detailed drawings of the tobacco factory and the Padrón household. Also inside: the would-be assassins’ passports and a minute-by-minute schedule of Padrón’s daily routine.

Padrón took the information to the Honduran police and the FBI, but both men had disappeared. Five months later, one resurfaced — in a pool of blood. The would-be kidnapper had been shot seven times outside his house.

“So imagine all these things that my dad has gone through,” says Jorge Padrón, José’s youngest son. “It’s almost surreal. But throughout all of this, he never lost focus on the thing that was the most important for him, which was to make cigars.”

The cigar world has recognized Don Orlando’s odyssey. In February 2005, Cigar Aficionado named one of Padrón’s puros the best cigar of 2004. Since then, Padrón has topped the list twice more.

Gracias a dios, we are selling our cigars in 71 countries outside the U.S.,” Padrón says with a stogy-stuffed grin. Now confined to a bright-red Rascal scooter, he still smokes four to five cigars a day.

“We are even selling to countries that were once Soviet!” he chuckles. “Arabs. The Chinese. Bulgaria. Sales are through the roof in Bulgaria! They can’t get enough of our cigars!”


In America, they say life is like a box of chocolates: You never know what you’re gonna get. But in Cuba, chocolate is rare and variety is vilified. Instead, life is like a box of cigars: consistent, predictable.

For Pepe Montagne, childhood in Havana during the 1970s was mind-numbing. Every morning, he walked to school in the shadow of the state-owned Partagás cigar factory, past the smokestacks that seemed to symbolize his family’s annihilated history. Every summer he worked in the tobacco fields like any other son of the revolution. And every 45 days, he visited his father — labeled an enemy of the state — in a dank prison cell.

The routine lasted until he left the island and put a match to the propaganda of the past.

If José Padrón is the grandfather of Cuban cigars, Pepe Montagne is the industry’s unruly stepchild. Like Padrón, Montagne overcame long odds to leave Cuba and start his own cigar company. But his life has been much messier, his battle with the Cuban government much more heated, and his future, if the embargo falls, much less certain.

Like Padrón, Montagne comes from a tobacco family. His great-grandfather moved from Lyon, France, to Haiti around the turn of the twentieth century. When tensions between blacks and whites boiled over, he moved to Cuba. He settled in Las Villas, a region in the middle of the island whose tobacco was second only to Pinar del Río’s.

Montagne’s grandfather, Tomás, stalked the family farms with a brucha — a paintbrush-like cigar — smoldering below his startlingly blue eyes. His son inherited his good looks but not his passion for puros. Instead, Francisco Montagne was a handsome mechanic more interested in chasing tail in Havana than growing tobacco in the countryside.

Francisco wasn’t without principles, however. And when Castro took power, Francisco joined a group called the Movement to Recover the Revolution. The MRR was a conservative Catholic group that spoke out against Castro’s increasingly Marxist policies. In 1962, Castro cracked down on the church. Two years later, soldiers arrested Francisco and imprisoned him on La Isla de los Pinos. Despite its pastoral name, the island was home to a horrific panopticon where Fidel Castro himself had spent two years during the mid-1950s. After the revolution, Castro turned it into a prison for counterrevolutionaries.

Francisco’s wife, Elsa, was six months pregnant with Pepe when her husband was incarcerated. When Pepe was an infant, Elsa took him on the sickening, daylong sea journey to see his father.

Pepe’s first memory is visiting his dad in another prison, an old castle called El Morro where guards ripped open the cans of food, fishing their hands inside the tins for contraband. Pepe remembers his father clad in nothing but underwear and a ragged white T-shirt with a P scrawled on it for político — a punishment for not confessing his crimes. Often, Pepe would find his father covered in fresh bruises or looking deathly ill.

“My father was tortured,” Pepe says. “To this day, he still has 92 machete scars on his back.”

Life wasn’t easy for the son of a political prisoner, either. At the beginning of every school year, Pepe would have to fill out a form listing his father as a “criminal” in order to enroll. “They tried to say that my father was a criminal, that he tried to kill someone,” Pepe says. “But I knew it wasn’t true.”

Whenever his fellow students sprayed anti-Castro graffiti on the school’s walls, the soldiers came looking for Pepe. And as soon as he was old enough, the government made sure to send the teenager to the tobacco fields to work during the summer, as if to taunt him with a glimpse of the lands his family had lost to the revolution.

Pepe reacted by becoming as American as possible. He hung out in restaurants, chatted up tourists, and sold watches on the sly.

When Pepe was twenty, his dad was suddenly released from prison. Pepe had never lived under the same roof as his old man. Now he suddenly had a dad bossing him around. Pepe moved out. A few years later, he married a Mexican woman and moved to Argentina with her. The marriage didn’t last, but he won an American visa lottery.

Montagne moved to Miami in 1996. Like José Padrón before him, he arrived with little money and few connections. Little Havana was now covered in cigar shops, though, and he found a job selling cheap bundles of smokes. He wasn’t an expert like Padrón, but “tobacco was in my blood,” he says.

“You can’t separate a Cuban from his cigars,” he says. “It’s like wine for the French. Go to Cuba tomorrow, and you’ll find 10 million people trying to sell you a cigar.”

Montagne was lucky. It was the height of the cigar boom in the United States. He could buy a bundle of inexpensive Caribbean cigars in Little Havana for $12 and flip it for twice that amount in Miami Beach. After six months of selling the cheap stogies, Montagne decided to move up in the supply chain by starting his own brand. He began buying Nicaraguan tobacco and importing cigars from Estelí.

All he needed was a name.


In mid-June 2002, Pepe Montagne received a package at his Calle Ocho cigar store. Business had been brisk. Montagne had moved up over the years from cheap-smoke peddler to manufacturer of his own stogies, which he called “Guantanamera.” To him, the name evoked more than the famous song. In Cuban slang, it could also mean a mess, a dance rhythm, or a curse. Whatever customers took it to mean, it was catchy.

Montagne had applied for a trademark a year earlier. And as he tore open the cardboard wrapping, he now hoped to see his dream finally documented on paper.

Instead, he found a nightmare.

“Opposer, CORPORACION HABANOS, S.A. (hereinafter ‘Habanos’), believes it will be damaged by registration on the principal register of the mark GUANTANAMERA,” the lawsuit began. The Cuban government’s tobacco company was accusing Montagne of deceit, claiming he was trying to swindle customers by confusing his cigars with theirs — a cheap, machine-rolled cigar sold worldwide.

To Montagne, it felt like a witch-hunt. His cigars were better, and he had come up with the name long before Habanos.

“The Cuban government has persecuted my father, persecuted my family, and is now persecuting me,” he says. “It’s crazy.”

The trademark battle would pit Montagne against the Cuban government and its phalanx of high-powered American lawyers for more than a decade.

It would also preview a much larger war. Over the past quarter-century, the Cuban government has systematically prepared for the end of the blockade by snatching trademarks and suing competitors.

Now that President Obama is actively dismantling the embargo, Cuba is poised to pump its cigars into the United States for the first time in half a century. The competition could effectively kill Miami’s cigar industry. Even famed local cigar makers like José Padrón will be adversely affected by the flood of Cuban stogies. Small guys like Montagne, already under legal siege by the Cuban government, could be blown out of the water.

“The Cuban government is like a snake,” Montagne says. “Everything it does is planned ten years ahead of time.”

Wrapped tightly around American courts, Cuba’s constriction of the cigar industry has already begun.

This is the first of a two-part series. Read part two, “Cigar Wars.”