The Once and Future Kingpin of Havana

The original publication can be found here.


While we never planned to meet Jorge, he certainly planned to meet us. In many ways his livelihood depended on it, stumbling out of the telephone-booth entrance to La Zorro y El Cuervo and right into the lap of his runner.

By now we were accustomed to the hustlers, every other question a variation on “my bro — where are you from?” Early in the trip a young dancer from Brooklyn warned us of these scams, instilling us with his lesson that “everyone here is trying to fuck you.” That we were sharing a bottle of rum with local Cuban kids who were presumably “trying to fuck us,” showcased the complexity of his advice. Most Cubans are poor; most tourists aren’t. Of course they’re trying to take you for a ride, and of course they want a few free drinks. The beauty of Havana isn’t that everyone is trying to screw you over — it’s that it’s kinda fun to let them.

Jordan, who referred to himself as “Mikael Jordan” with a wry smile, was as friendly and engaging as any other hustler. The corner outside of the jazz club bustled with men like him and the type of women that our Airbnb mother warned my traveling companion and I about. They live on supple American wallets, coaxing nervous tourists with promises of “one day only cigar fairs” and exotic chicas.

But all Jordan wanted, for now, was to grab a drink in a nearby hotel. And hey, why not? It turned out he was a Falcons fan, and that’s all I need to make a new friend these days. Besides, there were two of us, granting an (unearned) sense of security that made it seem like a good idea. Or, at least, not a bad idea. Then again, that may have been the cheap Bucañero beer in our blood.

Cuba’s Miller Lite, but more Pirate-y

Cuba’s Miller Lite, but more Pirate-y

The hotel lobby, predictably, wasn’t just for us and Jordan. It was decked in faded mid-50’s furnishings, with a small TV broadcasting a mid-90’s Schwarzenegger flick behind the bar. The bartender eyed us wearily, as if everyone in the building knew why we were there except us. Other than the occasional suit popping out of the elevator, everyone in the lobby seemed like a local.

In the dead center, rocking a camo Dodger’s hat and a thin cigarette, was Jorge.

As I bought the gang mojitos (because who doesn’t buy a round when the drinks are only $2?), I overheard Jorge, in near perfect English, extolling the virtues of his cigars. I tried to ignore him, hanging instead with Jordan while getting to the bottom of what makes Julio Jones so damn good (this was before the Super Bowl, when morale was still existent). The bartender, with the sort of look you give a kid getting bullied on the playground, gamely poured another drink, on the house. My American companion laughed behind me, asking how, if this co-op was one day only, we’d been offered the exact same thing yesterday? I heard no coherent answer.

This wasn’t the first time we’d gone along for the ride. We’d already learned that the best thing to do with a hustler wasn’t to back off — it was to lean in. At least that was the most fun, and the best way to meet people. So in we went.

By round three, the heat was on. In between bouts, we asked Jorge where he learned all his English, trying to dig into something other than a sales pitch. But the slightest indication that I may be interested in a box of Cohibas led Jorge to casually wave his hand, bringing over a man we will only ever know as “Gold Teeth.” The reason should be obvious.

We should have been afraid. The numbers were now 4–2 in the hustlers’ favor, and we had no idea, really, who the rest of the gang around us was. Being 3AM in a hotel lobby, we could have been surrounded by anyone. The elevator nearby swallowed and spit out a steady string of men and their tepid companions, half of these pairings coming right back out 20 minutes later. Gold Teeth, like a tobacco-wanded magician, stuck a huge stogie towards my mouth without naming a price. I was sober enough to refuse it. I pulled out my wallet, knowing it only had a few bucks in it, and they looked at the empty leather with slight disgust.

“What makes you think we have any money?” we asked. Cuba may be a cheap country in comparison to the US, but $140 for cigars was a lot of cash for struggling creative-types. Especially since I still don’t really know how to smoke them. I debated bringing up my student loans, but I knew fully well that their education was free and it would just offer a (deserved) dig at America.

Finally came the crux — the salespitch losing all subtlety and my butt creeping ever so slightly out of the seat. “Why wouldn’t you buy them? These are real Cohibas for 50% off!” They offered to drive us back to our hotel free of charge to get money, an idea so ludicrously brazen that all we could do was laugh. They promised us that, even if we waited until tomorrow, the price would go up considerably. But we knew we were being hustled, we knew the cigars were fake. And I think, on some level, they knew that we knew. Anyone sensible would have left. But we hadn’t, and that indicated we might just be bullied into buying them.

To be honest, we were thinking about it.

Finally, we just told them to stop. “Look — we don’t buy things that expensive when we’re drunk.” And Jorge, hand over his mouth in contemplation, simply nodded. “You know what?” he said, “I respect that.”

Deep in Havana after midnight

Deep in Havana after midnight


And from that point on, Jorge was done selling.


I grabbed another round of drinks and set out to determine where Jorge learned all of his English. It turned out he’s a basketball fan, a hell of a shooting guard in his day, and this hotel was the only one that broadcast NBA games. Brought stateside for a basketball scholarship, Jorge ended up on the Upper West Side. And, much like this hotel lobby, NYC was a place where basketball, Americans, and hustling couldn’t help but intermingle.

Over our 4th mojito and as many cigarettes, Jorge explained how NY in the 80’s made a drug dealer out of anyone. It wasn’t with self-judgement or worry, as he seemed to intuit that views of drug dealers were shifting in America. It was just a fact. “My name is respect — on the court and on the corner,” he said, a line I’d think he stole from The Wire if it were at all possible. Most importantly, however, I knew that he meant it. And that gaining his respect, even in the smallest amount, was the most important thing we could have done in Cuba.

Gold Teeth slunk back to a corner table, angrily stuffing his cigars back into the pouch around his waist. With increasing fascination, I asked Jorge why he came back — if he preferred being here to New York. He came back for family, he said, but he demurred on the second question. It was with little surprise that he brought up Donald Trump.

“Every time one of you puts a Democrat in, things get a little better. Every time you put in a Republican, it all goes right back to before.” When I brought up Elian Gonzalez and George Bush, he jabbed his cigarette towards me in artful punctuation, but he said little more on the matter.

Much more exciting were Jose Marti and Steph Curry, true “monsters, titans!” of the world and thus more deserving of our conversation. With a shrug, he tossed out the most casual estimation of Fidel I’d yet heard — “he got me an education, and he did some shitty things” — before moving on to why the NBA shouldn’t have let KD go to Golden State.

And if this wasn’t the most Cuban of nights, then came the cocaine. Jorge, with a wry smile, mentioned that he hadn’t done this in a long time and immediately hit three consecutive bumps. Back in the lobby, I hurriedly ordered more Mojitos and scribbled Jorge’s phone number in my notebook. We promised to call him tomorrow — Gold Teeth and Jordan making a last ditch effort to press the cigars on us — and then we headed back to the Malecon and our apartment.

The Malecon, Havana’s social promenade overlooking the ocean

The Malecon, Havana’s social promenade overlooking the ocean


The next day, hungover as all hell, we decided to call Jorge and let him know that we weren’t buying any cigars. After 6 missed calls on a broken payphone,we finally reached him, expressing our disappointment but hoping we could see him again. Despite some grumbling he agreed, and we went on with our day. It was far calmer than the one before it — we had a night to steel for.

Several hours later we were back at El Zorro y Cuervo to catch Roberto Fonseca, another one of Jorge’s “monsters.” And Jorge was right — Fonseca is a titan on the piano, with a backing band so effortlessly in sync they made improvisation seem like symphonic composition. And, sure enough, we ran once more into Jordan on the street, this time in a fresh Falcon’s beanie. With a smile, we headed to his apartment and bought a bottle of rum, bumping Run the Jewels 3 on the way and laughing like old friends. It could have been the booze, or the no-longer awkward language barrier, but we couldn’t stop smiling.

Restlessly roving the streets, we ended back near the bar. My friend came up with a new hustle, one where us, the American boys, played the role of confidence men. If Jordan and the gang had a set of white, English-fluent spokesmen, we reasoned, it’d be much easier to sell a few illicit cigars. A group of polo & visor-clad frat bros, yelling at a bouncer and smugly talking shit on the jazz musicians, revealed themselves as prime targets.

But before we could set things in motion, here came Jorge.

The parts of town the feral cats claimed

On the street we were confronted with a very different image of the man. To use his own words, Jorge was a monster. Each group of men that approached us always approached him first, each introduction beginning with a kiss on the cheek. It was a greeting we saw nowhere else in Cuba — at least not between two men. When someone intimated that Jorge might be a bit tipsy, he quickly let them know that, if he was drunk, he’d be in bed. And they best not imply otherwise. The streets listened, and that was the last we heard of it.

Some unknown amount of time later we were in a taxi, and Jorge had his hands around our shoulders in the back seat. Gold Teeth showed up somewhere in here, but we scuttled away before he could make a more permanent impression. We were in a hurry, it seemed, to buy some weed. The taxi driver knew what to do.

I mentioned that Jorge garnered a lot of respect in Havana, and he nodded solemnly. “It’s because I give respect when it is deserved,” he said, our conversation suddenly taking place in the streets again. As if to drive the point home, a woman came out and yelled for us to be quiet or keep moving. With a little nod, Jorge shuffled us away. “I know that woman,” he said, “and I respect her.”

We’d made it to “El Barrio Caliente,” a series of streets Jorge referred to as “real Havana.” The slums. It felt more akin the Upper West Side of Jorge’s youth, the stories of which became increasingly more graphic with every swig of rum. “And if they came for me, if they came for my family’s money,” Jorge said, continuing a story I don’t remember him starting, “then I made sure they respected me.” And respect, if his sudden pantomiming was any indication, came from the end of a pistol.

The quest for weed, much like those in my youth, led us down a lot of dead ends and awkward conversations. My pal turned to me and mentioned that we should be ready to run, and I agreed. For the first time, Havana felt a little hostile.

Even Jorge’s arm around my shoulder, once a small comfort, now felt suspicious. The streets were devoid of life other than us and a few stoop kids, one of which demanded I give him a dollar. When I asked why, he simply repeated the question. We walked off laughing, but they were not as amused.

Still, Jorge let us know that we had nothing to worry about. “If anyone screws with you, Nicholas, I’ll fuck them up.” Jorge’s cup of rum was empty, and he showed us exactly what he meant with an imaginary attacker, his knees and arms flying in drunken karate. “In Cuba, you have nothing to worry about. Not unless you live here. Someone tries to hurt you, you just tell me.” He attempted to wring a few more drops out of the cup. “I’ll fuck them up.”

Luckily, we didn’t have to ask. But there was one exception. Navigating the streets, I asked him what to do if the cops showed up. Should we run? Stay put? And what do we do with the dime bag of marijuana that appeared, to my eyes, out of nowhere? “The police?” Jorge said. “In that case, it’s your turn to protect me.”

Havana in 2017 or the Upper West Side in 1987. The distinctions were getting harder to draw.

But before long we were all smiling again, the darkened streets majestic with their crumbling, colonial architecture. Some of Havana’s most striking features are the buildings: big, ornate structures that would feel at home in Paris if it wasn’t for their dilapidation. Even the slums recall a former glory, a hallmark of the days when the gangsters running these streets were American instead of Cuban. Then, adventure-seeking Yanks crashed these shores for drugs, rum, and a good time, the Cuban people inviting the flood of capital without understanding that it concentrated into the hands of mobsters and corrupt politicians. This long con, never more evident than in the false promise of Havana’s architecture, may be coming back around under our Tangerine-in-Chief.

Except this time the common man isn’t going to miss his cut.

The only difference between then and now, it seems, is that this time the Cubans are ready for us. If Donald Trump, Visa, and Marriott are going to invade the Malecon once more, if young punks like us are going to keep fleeing to “a simpler time,” then Havana must be ready for us. Cuba beckons seductively, so why should we be surprised if, every now and then, it tries to fuck us?

“You are part of a Cuban family,” Jorge slurred slightly, though he was definitely not drunk and no one better say otherwise. “I want you to see this, to see this part of Cuba.” He knew we weren’t “real tourists,” but we were tourists nonetheless. He knew we were going to pay his taxi fares, and he knew that the next pack of cigarettes was on us. But he also knew he had a chance to give us a different side of Cuba. His side. Even if it was only for one night scoring drugs. And we were eating it up.

He wasn’t hustling us any more than we were hustling him. It’s just that his hustle, the quest for cash, was right on the surface. Ours was something a little more difficult to define, a persistent effort to leave behind the baggage of being American, if only for a second, and stumble our way into something resembling authenticity. And who is more authentic than a hustler who tells you exactly what he wants? If everyone is trying to fuck you, you might as well enjoy it.

With a tired smile, we let him know that we wanted to head home, and he handed us our share of the marijuana. “We will see you again?” Jorge asked, and we assured him we would. “Good,” he muttered, “and let me know if you change your mind about those cigars.

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