Of all the dead white male writers, Ernest Hemingway is the deadest and the whitest and the malest, vanquished as an icon and relegated to the losing side of so many histories. He is an embarrassing cliché. Even here in his home, La Finca Vigía, he is a monstrous joke.

The house is low and flat and white, and despite the hustlers and the unloading tour buses and the small bar cranking sugarcane for overpriced pineapple drinks surrounding it, the place retains most of its dignity. The desks, at which he never wrote, look like he could work on them today if he suddenly gave up the habit of a lifetime and decided to write sitting down. The original sofa Clark Gable slept on because the beds were too short is still there, and the pool in which Ava Gardner swam naked—"the water is not to be emptied," Hemingway told the pool boys—sits empty. The rooms are stuffed with memories, which happen to be some of the greatest written memories of the twentieth century: an enormous Cape-buffalo head redolent of "The Snows of Kilimanjaro," the bullfighting posters that could serve as covers for The Sun Also Rises. With the windows thrown open, Hemingway's house is both airy and compact, calm and full of life.

Then the U. S. senators show up and Al Franken can't stop cracking jokes. He mugs with a gigantic set of wapiti antlers in the small dining room, eking out a laugh from an audience of aides. Switching from slapstick to character work, he tries out an impersonation of a real estate agent, whispering conspiratorially to a bystander that he likes the place but the kitchen needs remodeling. At the dog cemetery—yes, Hemingway had a small dog cemetery, right beside the swimming pool—Franken notices a grave marked LINDA. "Was that one of the mistresses?" he asks the guide, who joins in the mild, polite laughter American big shots are entitled to. Franken senses a comedic win. "Do me a favor," he presses. "One out of every ten tours, you should tell them that's his mistress."

As the senators drift back from the dog cemetery, down a shaded stone path back to the main house, I ask Franken what everybody here is asking himself: What's going to happen to Cuba now that the embargo is about to lift? The man takes a stab at being a U. S. statesman in a foreign country. "Well, I think it's about to change," he tries ponderously, with professional noncommitment. Then he can't stop himself, looking up with that smile borrowed from the Joker. "I just wanted to get here before the Chipotle."

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Hemingway wrote his first piece for Esquire a thousand issues ago, and there's still a copy of the May 1935 issue poking out from a magazine rack in the living room of La Finca Vigía. Hemingway in Cuba made Esquire and Esquire, before that, made Hemingway in Cuba.

Before the magazine had a name, Arnold Gingrich, its founding editor, traveled from Chicago to New York to stalk Hemingway, eventually bumping into him at a rare-book shop he was known to visit. "It is not too much to say that, at the very earliest point, he was our principal asset," Gingrich remembered in his column after Hemingway killed himself in Idaho in 1961—far, far from the Havana he loved.

It seems Hemingway wanted a $7,000 boat. He had $3,500 from his second wife, Pauline, who was recovering from a terrible Caesarean birth and was determined not to get pregnant, and because she was Catholic and didn't believe in birth control, they had only coitus interruptus, and she gave him money for the boat because she needed to bind her husband to her in some way. Gingrich managed to find most of the rest—to bind Hemingway to Esquire—and together they bought Pilar, a marlin-fishing vessel built to Hemingway's specifications that sits on a dry dock at his house in Havana now.

The history of the star magazine writer begins with this purchase.

Here's a boat. Go write about the sea.

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Was Hemingway an asshole or a piece of shit? The distinction matters. Anybody can be an asshole from time to time, but a piece of shit is a piece of shit forever. Existence or essence?

Even a cursory look at Hemingway's intimate life, the life he kept from his writing, shows that it's one or the other, very probably the latter. If you were his friend, he was more than likely to betray you. If you were his kid, he was going to ignore you. If you were his wife, he was going to beat you. His monstrosity was at least half of him. A fishing rod and a pen and his prick were much the same device to him: a stick for poking the darkness, a weapon with which to encounter and defeat the world. Hemingway's love for nature was in destroying it. The rhinoceroses hunted in "The Short Happy Life of Francis Macomber" are now so near extinction they have armed guards to protect them from the kind of person Hemingway was. The thousand-pound marlins that Hemingway wrestled from the Gulf Stream have more or less vanished; the waters off Cuba have been emptied of the beasts he craved killing.

His manliness has also been depleted by time. The macho of Hemingway now appears so obviously as a front. Gertrude Stein knew it when they met in Paris. "When I first met Hemingway he had a truly sensitive capacity for emotion," she wrote, "and that was the stuff of the first stories; but he was shy of himself and he began to develop, as a shield, a big Kansas City–boy brutality about it, and so he was 'tough' because he was really sensitive and ashamed that he was." That was the modus operandi of another generation: the grandfather who came back from the Second World War and never spoke about it, the uncles who drank themselves and their secrets into oblivion. Hemingway kept up the front of the hard man to hide the thorny vulnerabilities within him.

Now men have figured out another trick: We act weak to hide the hardness of our hearts. We display vulnerability to preempt judgment. We have been overwhelmed by sanctimony; the public shaming of the Internet means that outrage is the dominant tone of the dominant medium of our time. Somehow we have drifted, all of us, into the general assumption that the appropriate response to everything—even comedians and R&B songs, never mind novels—is to test them against the established pieties of the moment. In this miasma of affected virtue, correctness becomes paramount in our personal lives as well. How many men do you know who live oh-so-correctly? Not embarrassed, not saying the wrong thing, not saying it in the wrong way; virtuous and useless. The new sanctimonies of the Left and the Right are much the same; they have the same result, anyway: certified writers who leave no trace behind and approvable men and women who amount to nothing. The would-be blameless ones.

The problem with sanctimony is not that it's wrong but that it doesn't acknowledge the fundamental messiness of human nature and of life as it's lived. Breathing in Hemingway is like breathing in the foul Havana air, half-perfume, half-diesel. He is rawness and boastfulness and bloody-mindedness and he once shot himself while he was trying to shoot a shark and he never had a kind word to say about the men and women who established his career and he slept with vulnerable strawberry-blond girls and he patrolled the waters off Havana for German submarines in a fishing boat like some boy's own adventurer and he took strange young men who showed up at his door on monthslong fishing expeditions and he tipped big with his wives' money and he despised Fulgencio Batista and he shot lions and he wrote books. It's all there in The Sun Also Rises: Go and watch a man kill a bull and then watch the man who killed the bull fuck a woman. Call it life.

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Hemingway's first piece for Esquire was "Marlin off the Morro: A Cuban Letter," a great essay crackling with that electric Hemingway stuff. It appeared in Esquire's first issue in fall 1933. "The 468 pounder was hooked in the roof of the mouth, was in no way tangled in the leader, jumped eight times completely clear, towed the boat stern first when held tight, sounded four times, but was brought to gaff at the top of the water, fin and tail out, in sixty-five minutes." Readers ate it up. Esquire, at the lowest point of the Depression, sold half a million copies a month at fifty cents a copy, mostly on the strength of Hemingway. During the thirties, Hemingway wrote twenty-six articles for Esquire, along with classic short stories like "The Snows of Kilimanjaro." He left in 1937 to write for the short-lived left-wing magazine Ken, also edited by Gingrich, mostly on the Spanish Civil War, but even when he was gone Esquire kept printing him. In the forties, Esquire reprinted the entirety of "The Snows of Kilimanjaro," all of the thing's nearly ten thousand words, but accidentally called F. Scott Fitzgerald by his real name for the second time. Hemingway was pissed.

When you think novelist now, the first word that pops into your head is meek and the second is wounded—definitely not pissed. Writers today are Brooklyn and Hemingway was Havana.

From a brand perspective, Jonathan Franzen is the closest thing to a Hemingway-sized writer now living. When I e-mailed him to ask about his thoughts on Hemingway, he was polite but wrote that he didn't want to talk about him; he just didn't care enough. I assumed Cheryl Strayed, a writer who, like Hemingway, reckoned a wild identity in the struggle with nature, would hate him. He was, after all, a hunter and a prick, exactly the kind of dangerous man she had to avoid on her journeys as chronicled in Wild, but she only vaguely remembered him from high school English class. She recalled, distantly and fondly, the sad beauty of "Indian Camp"—like a long-dead great-great-uncle whose vices as much as his virtues bring out a sentimental but distant attachment. He didn't matter enough to hate him.

Of all the great modernist writers, Hemingway is the least admired but the most imitated. Serious readers worship James Joyce. They worship Kafka. They worship Borges. But nobody tries to write like them, not in America, anyway. And yet every section of the bookstore shows Hemingway's influence. "When you find a good line, cut it" was Hemingway's advice to the writers of the future. In his lack of metaphors, emphasis on curt description, strong active verbs, and masses of dialogue, he has had more influence on someone like Elmore Leonard than on even Raymond Chandler or Jim Thompson. Two of the greatest film noirs of all time—The Killers and To Have and Have Not—are Hemingway stories.

He has been equally influential on the high-lit crowd. He invented youthful Americans suffering anomie and wandering interesting cities without explanation, a pattern followed at regular intervals ever since, the latest examples being Tao Lin's Tai Pei and Teju Cole's Open City. The self-writing of Karl Ove Knausgaard, Ben Lerner, and the rest—the literary trend of our hour—draws a peculiar kind of strength from inverting Hemingway's project. Their trick is that they tell you about the banality of their lives and do so in such a boring way that it must be true.

Just to enumerate those under Hemingway's influence—Raymond Carver or James Salter or Cormac McCarthy, say—kind of misses the point. It's not like writers are reading his books and admiring the sentences and imitating them or imitating his imitators. Because they no longer have to. The man is gone—a violent white male chauvinist, better left in the rear view of history. But his style lives on. In high schools across the country, clear, concise writing is simply taught as good writing. Hemingway—if not his name, then his style—became the rule.

If anything, it's the Hemingway proposition—that a writer should live a life worth being written about—that today's novelists still wrestle with. He was there at the origin of our particular crisis of authenticity: the realest man alive and then, soon after, the fakest, writing his life but only a tiny fraction of it, the tiny fraction that he wanted the world to see.

Paul Hendrickson's Hemingway's Boat includes a letter Gregory Hemingway wrote to his father: "When it's all added up, papa, it will be: he wrote a few good stories, had a novel and fresh approach to reality and he destroyed five persons—Hadley, Pauline, Marty, Patrick, and possibly myself. Which do you think is the most important, your self-centered shit, the stories or the people?" Sixty-five years later, Gregory's question can have only one answer: The stories mattered much more than the people. The people, except for Patrick, are all dead. The stories aren't.

Like his clean, pared-down style, his stories live. They haunt. Last summer, I saw my son sitting on a dock, his feet dragging in the water in the light of lazy contemplation, and I thought of that line from "Indian Camp": "In the early morning on the lake sitting in the stern of the boat with his father rowing, he felt quite sure that he would never die." I heard that my grandfather had finally moved into a veterans home and I thought of that line from "The Killers," spoken by a boxer about to be killed: "I'm through with all that running around." A friend's baby died from SIDS and I thought of that line from The Old Man and the Sea: "A man can be destroyed but not defeated," and I wondered if it was true. Literature survives for the crude reason that, in the crises of our lives, it is useful. Hemingway remains useful.

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Hemingway is a very useful guide indeed, for bars and hotels and fishing in Havana. The Hemingway experience is not so much a movable feast here as a desultory amusement park. In the Ambos Mundos hotel, you pay two dollars to visit the room, untouched since his departure, where Hemingway wrote A Farewell to Arms and Green Hills of Africa on a standing desk scavenged out of a stout piece of square wood, with a pair of rotating screws underneath for raising and lowering the height. In the opening of "A Cuban Letter," Hemingway described the view: "The rooms on the northeast corner of the Ambos Mundos hotel in Havana look out, to the north, over the old cathedral, the entrance to the harbor, and the sea, and to the east to Casablanca peninsula, the roofs of all houses in between and the width of the harbor." It is exactly the same today. A photograph of Hemingway and Fidel looms over the bed.

They make mojitos at La Bodeguita del Medio the way they make burgers at a church picnic—without fuss, to be knocked back without thinking about it too much. Here, the first wave of American tourists has already landed. Not just the adventurous ones who used to come through Canada or Panama and made sure their passports weren't stamped. I'm talking little blond girls from California who look at the handmade beaded-handle purses on the street and discuss plans for mass-manufacturing imitations in China—not really for the cost savings but "for the consistency of the product." "You know what these people need to learn is to bring the drinks faster," a lighting designer from Milwaukee drunkenly slurs in my ear. "That's where the money is." A northern Californian, sporting a guerrilla hat with the red star on it and a shirt with Obama's face transposed onto the image of Che, explains his choice of men's wear: "You need to leave the house with a narrative." He was having "a Commie weekend." You can buy an apartment in Havana, they say breathlessly, for ten grand. What's that going to be worth in fifteen years?

At El Floridita, the self-proclaimed "Cradle of the Daiquiri," a life-sized bronze sculpture of the man watches an endless procession of tacky, excellent bands play Cuban music that tour groups might recognize as Cuban, and the drinks are the outrageous price of six dollars a pop. Which means that two drinks and a tip comes to the monthly salary of a typical Cuban worker. El Floridita may be tacky and touristy, but it is a hell of a fun bar. Smoking a cigar in the afternoon as you sit in a cool, dark place slowly drinking syrupy cocktails through a little pink straw is its own shadow of paradise. El Floridita is the kind of bar where you find yourself buying rounds for strangers and then they're buying rounds for you, and eventually you're taking photographs with a bunch of fishermen as they storm the small stage to dance with slim-hipped women in fuchsia dresses with plastered-on smiles, and then you realize it's only three in the afternoon. Hemingway is always there, smiling benevolently from the corner. Everyone wants a picture with him. Everyone wants to throw an arm around him. He dignifies the proceedings—the sinful patron saint of alcohol and fishing stories.

Here's the thing: When you are in Havana, you are not seeing cars like the cars Hemingway saw. You are literally seeing the same exact cars. Hemingway suits this out-of-timeness—his relics are sacred in the most direct way. Hemingway left his Nobel prize medal in the sanctuary of El Cobre, the Cuban equivalent of Lourdes, outside Santiago de Cuba, on the southeastern coast. It, too, is a crumbling city with dark corners and several different pasts. The Hemingway business sells his essence of life, but that essence is not so different from Cuba itself—raw and unhinged and trapped in several different histories, and handmade and gorgeous and fleshly and occasionally cruel. He called himself a "Cuban sato"—a Cuban mutt—in an interview with Cuban television after he won the Nobel, telling them that The Old Man and the Sea was "based on Cojimar, more or less my town."

The American Hemingway failed. The American Hemingway killed himself in Idaho. He got tangled in the wires of his self-mythology and finished with the line "The world is a fine place and worth the fighting for and I hate very much to leave it." The Cuban Hemingway never failed. He didn't need to defend the world. The Cuban Hemingway somehow is more alive now that he's dead. He has just left Havana and will probably come back any moment. You can still imagine him bringing old friends and some dancer he just picked up to the bar for a long afternoon binge. You can picture him writing in the mornings and then strolling off to the nearby woods for a bit of shooting. You can imagine him setting off for a day of wrestling with the sea. The ghost of Hemingway in Havana is a benevolent spirit. He watches over fishermen. He brings tourists into bars to pay for expensive drinks.

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Good old Arnold Gingrich, a blithe, life-loving spirit and an excellent writer on fishing himself, built the Hemingway industry and fell victim to it. In an editor's note he came to regret, Gingrich compared his star writer to Cézanne for changing the "way of seeing" in American literature. Later, he married one of Hemingway's mistresses, a volatile strawberry blond, the lovely and glamorous Jane Mason, whom Hemingway reduced to the wealthy bitch wife in "The Short Happy Life of Francis Macomber" (intended for Esquire but published by Cosmopolitan in 1936). To Have and Have Not contained a nasty portrait of Mason too, and while Hemingway and Gingrich were out fishing, the editor brought up the slander against his future wife. Hemingway thought she should be flattered to be mentioned at all. Gingrich remembered the scene in Esquire and later in his memoir:

"It's a little like having Cézanne include your features in a village scene," [Hemingway] pointed out modestly.

I thought he was kidding, so I asked, "you aren't mixing your métiers, by any chance?"

"Not really," he went on evenly. "After all, what I can't get through your Pennsylvania Dutch skull is that you're not dealing with some penny-a-liner from the sports department of the Chicago Daily News. You're asking for changes in the copy of a man who has been likened to Cézanne, for bringing a 'new way of seeing' into American literature."

I almost fell out of the boat. This outsized ham was quoting me to my face, and without giving me any credit.

In 1963, Gay Talese wrote about the first wave of his disciples in "Looking for Hemingway." For a particular breed of spoiled Ivy League dilettante, Hemingway was a cipher for Romantic-period literary escape from East Coast proprieties. The greatest networker of them all, George Plimpton, led these disciples. "One lonely night, before returning home, George took a walk through Montparnasse down the same streets and past the same cafés that Jake Barnes took after leaving Lady Brett in The Sun Also Rises," Talese wrote. "George wanted to see what Hemingway had seen, to feel what Hemingway had felt. Then, the walk over, George went into the nearest bar and ordered a drink."

James Baldwin knew all the wannabe Hemingways and saw through them all. " 'They also used to go to Montparnasse, where all the painters and writers went, and where I hardly went. And they used to go there and hang around at the cafés for hours and hours looking for Hemingway,' " he told Talese. " 'They didn't seem to realize that Hemingway was long gone.' "

By 1967, Esquire was already reporting on the parricides of Papa—critics and scholars and other novelists who were starting to dismiss the work because they so evidently needed to dismiss the man. Esquire joined in with the others as his aura declined. In 1981, James Wolcott declared the release of Hemingway's Selected Letters, at 948 pages, as "the last big bang of the Hemingway industry, the last log to be kindled in his honor." Malcolm Cowley defended him. So did James Salter. But it's all a piece of the fundamental sadness that in America, everything that grows too big must be taken apart and sold for pieces. Today, you can buy Hemingway glasses and watches. You can buy Hemingway furniture. Hemingway is just another goddamn lifestyle, with another goddamn industry to feed and feed off it. Like any brand, it has a shelf life. What you buy, you eventually throw away.

Here is what Cuba has said in resisting the American blockade over the past fifty-three years: We cannot be bought. And for better and mostly for worse, they have not been bought. And neither has their Hemingway. The opening of Cuba is not really an opening of Cuba. It's an opening of America. Cuba isn't tearing down any walls. America is. In Cuba's new openness, America will find in Havana a glorious, fetid human mess, and it will find in Hemingway its appropriately messy, appropriately glamorous ghost.

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On any given evening, the Malecón, the five-mile promenade along the Havana seawall, is the most interesting street in the world. The housing crisis in Havana is so severe that some families sleep in shifts, so in the evening, in the relief of the cool, the city eases out from its cramped neighborhoods and moves to the collective street. It is a spectacle of secular love. There are young bodies draped over each other, and middle-aged bodies ensconced in each other like stacked folding chairs, and old bodies tucked beside each other like worn bricks. There are stone-eyed fathers and sons silently sharing rum, mothers and middle-aged daughters arguing over the hang of a blouse, brothers screaming at each other about the minutiae of baseball. Political critique plays out in jokes. "Cuba has eleven million people and six million police." "We have three sources of information: Fidel, Fidel, and Fidel." What is secret in other cities is forced into the open here: An old white man lugubriously makes out with a young black woman; a girl pulls away from the bite of an overeager mouth; a family stops short, all at once, frozen in the shared, unspoken memory of another time by the strumming of a passing guitar. A few in the crowd face the sea, where ninety miles or so into the darkness, the United States of America lurks.

In Cuba, the memory of Hemingway is the stand-in for the memory of America, the loved and despised other country, the adored enemy, the closest place that is impossibly far away. His house, La Finca Vigía, is the rare case of a cultural artifact of genuine geopolitical importance. On the Cuban side, generations of preservationists have struggled against the embargo. It's not just the total lack of funds that has made the preservation so difficult; it's also the fact that most of the necessary equipment is produced in the United States—it was illegal to export Bookkeeper-brand paper preservative to Cuba, for instance. Then, in 2001, Jenny Phillips, who is, among other things, the granddaughter of Hemingway's editor, Max Perkins, visited Cuba and enlisted the aid of Jim McGovern, a congressman from Massachusetts, to help preserve this legacy. They began working with the Cuban authorities and the State Department to find ways to bring in American equipment and expertise. In 2002, the Finca Vigía agreement was signed. To everybody's surprise, Fidel himself showed up at the signing. (Due to the risk of assassination, Fidel's visits tend to be surprises, with commandos hiding out in the trees.)

"I gotta be honest with you," McGovern says today, "it was a little bit surreal. That I was sitting there, signing a document with Fidel Castro. And I was thinking, I hope I'm not violating the Logan Act or something." Hemingway is synonymous with the hope of reconciliation between the U. S. and Cuba. "He's the one thing we have in common. Everything else we fight about. The one thing that people cannot disagree about is Hemingway."

The embargo is still affecting the work of the house. Hemingway's old Chrysler needs pieces they can't yet bring in legally. There's a space for the Kenmore stove that he used in the kitchen. I assume some tourist who works at Chrysler and another who works at Kenmore will show up soon and just send them the parts. But they can't yet. I asked the director of the museum, Ada Rosa Alfonso, a woman with an auntlike sense of personal pride in the place, how many tourists she was expecting when the embargo lifted. They have eighty thousand visitors now, she explained, lighting a complacent cigarette, and they were expecting twenty thousand more. Surely she meant two hundred thousand more? No, she meant twenty thousand. To my discredit, I laughed. Ada Rosa didn't laugh. She shrugged.

"You cannot fit America into Cuba," she said. We will see.

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No one is having a better afterlife than Ernest Hemingway. No one is enjoying eternity more. Late into the night at El Floridita, drunk Quebecers plant kisses on his bronze cheeks. A Shenzhen businessman places a lit cigar to his lips for a laugh. In a quieter moment, in between sets, a middle-aged man with sloppy drunken eyes slides over to the statue. This man, I can tell, is an American because he regards Hemingway as his equal. He appears to be having some kind of conversation with the dead man, telling him his secrets, describing his divorce.

"I like to listen," Hemingway once said. "I have learned a great deal from listening carefully. Most people never listen."

He remains as omnipresent as ever—the Papa we hate but always come back to. In a dark tourist bar, on a tumbledown corner of one of the most isolated cities in the world, with everything about to change and everything about to stay the same, Papa listens, waiting for the rest of his countrymen.

Hemingway's boat, Pilar, which Esquire helped pay for; with a marlin in Havana Harbor in 1934, the year after Esquire launched; and sixteen years later with a shotgun, perhaps the one he used to take his own life in 1961.

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A bronze statue of Hemingway at his regular barstool at El Floridita. His standard drink, a Papa Doble: 2 oz white rum, ½ oz fresh lime juice, 1 tsp fresh grapefruit juice, 1 tsp maraschino liqueur. Shake well with ice.

For Esquire's 1,000th issue, October 2015 (on sale now), we look back on the history of the magazine and launch a digital archive of everything we've ever published, Esquire Classic.