Castro’s Cigar Hondlers Roll Their Own-and Me

All over Havana, touts want you to buy black-market cigars at a fraction of the government price, and they make

All over Havana, touts want you to buy black-market cigars at a fraction of the government price, and they make lewd pantomimes of puffing as you walk by shadowy alleyways, but it wasn’t ’til we’d been in Cuba a few days that my wife and I followed an earnest young man into the back of a decaying house in old Havana and up four flights of stairs. His friend stood lookout for the police.

The washing was out in the courtyard, and a man used a pulley to get a bucket to an ironwork balcony. It was an old mansion cobbled into a score of apartments, and it had that liberated feeling you often experience in Cuba, the feeling that the inmates have taken over the institution.

The guy had a neat little place with a table stacked with boxes. Colorful Romeo y Julietas. Masculine Cohibas. Partagas. Montecristos. We opened different boxes for a while, enjoying the luxury of it all, before settling on Cohiba Robustos, a five-inch cigar with a good heft, packed neatly in a dovetailed cedar box. Cuba only began making Cohibas after the revolution, and they say Fidel smoked Cohibas before he gave up cigars. A box sells for nearly $230. I paid $40 U.S. and figured I’d worry about customs later.

My friend John, an architect on Lafayette Street, and I smoked a couple of them walking down the Prado. We felt grand. The cigars were fabulous, and the setting majestic and ruined.

A few days later, I stopped by John and Susan’s “casa particular,” or private house, for breakfast. Under pretty strict regulation, private homes are allowed to serve as hotels and get around $35 a night. The place looked like a house in Pasadena. Marble floors, a white formica kitchen. Halogen lamps.

John was at the table across from a bullfroggish man with short blond hair, in a black shirt.

“This is Bobby,” John said. Bobby had a gold ring with his initials on them. (I’ve changed his name and a couple of facts about him.)

Bobby was from Chicago. He was in town for the annual Cigar Fair. Like us, he’d come through a third country, in violation of the embargo. But he said he also had a license to travel to Cuba to supply hospital equipment, under a humanitarian exemption to the embargo.

Bobby liked to talk, and I was at once spellbound by his cold intelligent eyes and oleaginous manner, and pretty confused by his layered agendas, cigars and hospitals. He told us why George Burns favored White Owls (they wouldn’t go out when he put them down on stage) and how much a good Cuban cigar could fetch back in New York–up to $50. The Cuban government price for a Robusto is $9. That’s why you have mules smuggling large quantities into the U.S. from Mexico. It seemed like Bobby had known a mule or two.

“The two big problems the Cuban government has is, one, the parallel market–people selling cigars for way less than the real price,” Bobby said. “The other is counterfeits–people selling fakes on the street, damaging the brand.”

John told him about my cigars, and Bobby shrugged. “Almost everything on the street is fake.”

A little later, when he got up to leave, he glanced at me and with an air of false modesty said, “Hey, what am I, the cigar macher –”

A bit of Yiddish in Havana. It was his way of saying he could tell I was Jewish. He had me; I smiled.

Later I told my wife about Bobby, and we were both fairly contemptuous. The fat know-it-all is a familiar type–at one point, Bobby even made a crack about my Spanish–and it bugged us that he would dismiss my cigars offhand.

John was also of the opinion that mine were authentic. They tasted great; the box was perfect down to stamps and embossing. You couldn’t fake that; there was a taut silk ribbon that went around the cigars and made it hard even to get them out.

That night, John and I did the town. We ended up at the Comodoro, a disco run by the Cuban government, teeming with young prostitutes and foreign men. The girls stood at the edge of the dance floor without acknowledging you. They looked like college freshmen, but with a hard, cool expression. I bought a woman named Maria a drink. She talked to me about how the economy will change when Castro dies. “Oh, when is he going to die!” she said. In 10 days in Cuba, it was the most open discussion I had about the future, something everyone there is secretly concerned about.

Our cab ride home was with a guy who spoke perfect English. It was clear he was professionally trained, and I felt a little embarrassed, but John pointed out later that self-esteem is a luxury of a rich society. The guy wasn’t ashamed; he was doing what he had to do to get dollars.

Since the Russians pulled out 10 years ago, Fidel has allowed two economies to exist in Cuba: one the socialist peso economy, where kids’ sneakers cost 15 cents and a bottle of rum 50 cents; the other a dollar economy, where you can get TV’s and fancy clothing. Anyone with material aspirations in Cuba has to claw their way into the dollar economy.

The next morning, my wife had an idea about how to set Bobby up, and we headed over to John and Susan’s.

First, we stopped at an artist’s house nearby. Under Fidel, artists, musicians and athletes are privileged. Art is everywhere, and there’s been a frenzy among New York galleries and museums to acquire Cuban art.

My wife had met one of Havana’s rising artists and was getting a painting on paper for $300 cash (it’s all an American can use in Cuba). The artist, whom I’ll call Haydee, lived in a beautiful neoclassical house with a garden and iron gate. She kissed my wife, and my wife said she smelled great.

“It’s Gio,” Haydee announced.

We went on to John’s. Bobby was sitting right where he’d been the day before, reaching for papaya chunks with his fork. We soon got to talking.

My wife said, “How do you reconcile a dual career in cigars and health care?”

Bobby stayed cool. “The people who get mouth cancer are the slobberers and the tonguers.”

Then I said, “Bobby, how would you feel if I brought by two of my Robustos and two authentic ones, and you try and tell them apart?”

Later, John said that he saw a spark of panic in Bobby’s eyes just before he said yes. Bobby did seem a little nervous.

“Don’t be a chozzer ,” he said, the Jewish word for trickster, and wanted to make sure I stuck by the rules and brought two of each.

We went to the Partagas’ factory in Old Havana for the authentics. The place was crammed with Europeans smoking cigars and magazines with Michael Douglas on the cover. I bought two Robustos at $9.15 a shot, then we walked to the Hotel Inglaterra for lunch. John lit up a Partagas.

The smoking test struck Susan as a little cruel, but John was in stitches over it.

“Don’t you see? There’s no upside for Bobby,” he said. “What’s the upside? We’re going to think he’s so smart? There’s only a giant, yawning downside. There goes his whole reputation, sliding downhill, right in front of us.”

My wife said that Bobby really had had no choice. If you’re an aficionado, you’re constantly testing yourself, trying to improve your powers of discernment. He couldn’t not accept the challenge.

Suddenly a big guy with a furtive look came running up to John and said, contemptuously, “You’re smoking a banana.” The guy plunked a box of Robustos in John’s lap and passed around his identification card that showed he was a tobacco worker.

The guy was desperate to cut a deal before the police came up.

John didn’t move from his chair. “I’m negotiating with my butt,” he said, with a laugh.

The man dropped his price from 40 to 35 to 30, and finally to 20, before picking up his box and rushing off.

I had to run, too. I was going off to San Jose, 20 miles outside Havana, to see Fidel give a speech opening a new school.

But police were crawling all over the town, and they wouldn’t let me in. As they turned my car away, I watched a man in worn-out boots bicycle slowly by. He had a giant cake for Fidel balanced on one shoulder. Nearly 50 years after he defied the court that imprisoned him by saying, “History will absolve me,” and 45 years after he stole back from exile on a tiny boat jammed with Che Guevara and 80 men, Fidel’s dedication and vision are still staggering.

It’s his hardheadedness about the future that seems a little insane. Under Batista, a lawyer like young Fidel Castro was allowed to engage in controversial discussions. Today, the lawyers are driving cabs. Ten days in Cuba and I never saw a newspaper. There was something intellectually suffocating about that. But then, all the thinking has already been done.

Bobby looked pale. He explained that he’d been out till 3 a.m. at the final dinner of the Cigar Fair, at the Tropicana. They’d auctioned off elaborate humidors stuffed with cigars for over half a million dollars to Arabs, Europeans and some closeted American buyers, too. One humidor went for more than $200,000, he said. Fidel had been there, in fatigues, to accept the money on the behalf of the Ministry of Health. So Bobby had seen Fidel; I hadn’t.

Finally, Bobby turned on the fan and fetched an ashtray from the kitchen.

Then he went to a back room and came back with a fiercely handsome sidekick, a Cuban man in shorts with a shaved head and a passing resemblance to Antonio Banderas, who looked around the table with a sneer before sitting down. Bobby introduced him as Nelson.

I held the street cigars in one hand and the authentics in the other. I asked John if he wanted to play, and he said, “I don’t think you want the yard man to appraise the Van Gogh, now do you?” That seemed to up the ante.

Bobby got very calm and very quiet.

The test was over before it began. My cigars were fakes; they knew it instantly.

Nelson and Bobby rolled them around next to their ears, listening to the density, then shoved them up their noses and shut their eyes. Nelson dropped his on the table a couple times. Falso, he pronounced.

“Look at the way it sits there. Like an egg,” Bobby said. “And the way it’s rolled–it will smoke like a chimney.”

I didn’t say anything. What was I going to say? My only retreat was epistemology, and Bobby beat me there, too. When I pointed out that he was smoking my cigar all the way down, so it couldn’t be all bad, he said, “It happens to be a Cuban cigar. So what if it doesn’t have a name on it?”

Somewhere in there, it turned out he came from a line of rabbis, and I realized what a perfect operator Bobby was for the new Cuba, occupied Cuba, Cuba secretly teetering on a dollarized future. Cuba is at once the most hedonistic and sternly righteous place you’ll ever be. It takes a deep and cold understanding of the human condition to navigate it, to drift down between layers of morality and shamelessness without getting bent out of shape about dignity. You had to have a deeply ingrained sense of irony. At the

Comodoro, the state disco and meat market, the bartenders were wearing priests’ robes as a costume. The prostitutes were the intellectuals.

Nelson went back to the room for a box of Robustos. He carefully broke the seal with his fingernail and lifted out all 25 cigars in a clump, holding them by the silk band.

“Smell that,” Bobby commanded. “It smells like the earth. See how dark and oily it smells. Yeah, a good cigar smells like shit.”

He had a whiff and gave them back to Nelson. “Nice box,” he said with the understatement of a connoisseur.

They had to run. Bobby shot me a last look through the smoke and turned with empathy to my wife.

“If I were you, I wouldn’t go through customs with him. He can be a putz .” Castro’s Cigar Hondlers Roll Their Own-and Me