A True Account of One Man’s Daring Attempt to Drink America’s Greatest Writer Under the the Table

Ernest Hemingway had rolled into Key West a couple of weeks earlier. After touring the local dives, he settled in at a rough and tumble joint called Sloppy Joe’s. There he held court with a gang he’d brought with him from Europe — a Spanish bullfighter named Miguel, some hot-shot photographer and a handful of other hangers-on.

 During one of those nights he took issue with a young fisherman named Marco. Seems the kid, barely in his twenties, made remarks to the effect that he could out-drink anyone in the joint, including any fancy writers who might be on hand. Soon enough the Spaniard came over and in pretty good English invited him over to Hemingway’s table. The old man looked him up and down and said, “What are you drinking, kid?”

He was drinking whiskey, straight. Hemingway nodded and the dance started.

Six hours and untold bottles later, the kid fell out of his chair. The bull stabber and the shutterbug helped Hemingway to his feet and as a goodbye, the old man poured the kid’s unfinished glass of whiskey onto his unconscious face — the worse insult you can give a man, if you ask me.

The kid was laid up in bed three days before he could even stomache soup. He was a mess.

He also happened to be my kid brother.

My father had raised the Pesta boys by this creed: “You pick on a Pesta, you take on the whole family.”

When I got wind of what happened, I quit my job and drove the 900 miles from New Orleans to Key West in one go. After looking in on Marco, I checked into a hotel then walked to Sloppy Joe’s. I staked out a seat at the bar like a hunter staking out a waterhole. I brought my duffel bag with me. Inside it I had a little surprise for Mr. Hemingway.

I got to know one of the bartenders that first night. His name was Carlos and he was a small, quiet man. He told me he’d emigrated from Cuba five years earlier, and, like all Cubans, he held Hemingway in great regard. When I told him what my plans were, he shook his head gravely and said, “You do not want to face him. He is untouchable. He has already tasted your family blood. He will know how to beat you with a glance.”

I told him not to be so sure. This time he wouldn’t be manhandling a kid who barely knew which end of the bottle to drink from. I’d spent four years in the U.S. Navy and six in the Merchant Marines. While in the Navy I’d held the middle weight boxing title on my destroyer for three years straight, but what I really prided myself on was my boozing ability. I’ve drank down 300 lb. sailors in Singapore, I’ve put tough-as-nails dock workers under the table in Bremen. Once I’d even had the opportunity to drink with Jumpin’ Jimmy Monroe, a former U.S. wrestling champ. He was famous for traveling the world and taking on all comers, in the ring and the bar. Twelve hours later one man got up from the table, and it wasn’t Jumpin’ Jimmy.

Hemingway didn’t show up the first night. Or the next. I thought of checking out the other bars in town, but my instincts told me to sit tight. Carlos suggested he might have went back to Europe, or New York, but I knew better. I could sense his presence, he was out there somewhere, moving around like an invisible king. Don’t ask me how, I just knew.

It was right after sunset the following day that my patience paid off. Now, I’m not one for celebrities. I can take ‘em or leave ‘em — in my mind they aren’t a bit different from your average longshoreman or waitress. They just happen to have more money. I’d read a couple of Hemingway’s stories in Life, and knew he was famous for being a tough guy, but I paid no mind. All he was to me was a guy I was going make look like a chump.

But I gotta admit, when the old man walked in the bar, I was kind of impressed. I’d been afraid that when I saw him, him being an old man and all, that I’d feel sorry for him and lose some of my anger. But I didn’t. He was with his gang — there were six of them — with a couple locals trailing them like hyenas skulking around a pride of lions. There was the bullfighter, he was easy to recognize, the bespectacled guy with half dozen cameras hanging from his neck was obviously the shutterbug. There was a tall woman and she was straight class. One of the others was a deeply tanned blond man with a hard look about him, the other two smelled of guys who made their living with typewriters.

At the front was the old man. He had a pretty good beard going and he moved with a slow, ponderous deliberation, like he was reaching the end of a long journey. I tried to shake it off, but there was something big about him, I had two inches of height and maybe ten pounds on him, but he moved like a loaded freighter easing into dock, like he weighed a cold ton.

The gang moved like they had one mind, there was never any hesitation. They crossed the room and sat down at a table near the bar, nobody talking. Carlos got busy with a shaker, he must have known what they wanted, and I got myself ready. I rose from my bar stool, turned to the table and froze.

I have to tell you, I’d been envisioning that moment for the past three days, over and over — I’d march right over to him with a bottle of rum, slam it on the table and say, “You got my little brother pretty good last week. Now I’m going to repay the favor.”

But I froze. I stood there like an imbecile who couldn’t decide if he was going to jump three feet in the air or fall on the floor. Then I remembered my brother lying in bed like a cripple and I got mad and started for the table.

I was halfway there when I realized I’d forgot the bottle of rum. Kind of relieved, I turned around and went back to the bar. Carlos was still busy making their drinks and I was relieved at that too. A shark could have leapt up out of the ice trough and bit my drinking arm off and I would have been relieved.

I’ll admit it, I was scared of walking over to that old man. This from a guy who’d hunted sharks with nothing more than a spear gun and a snorkel, a guy who’d strolled into a Panamanian police station and slapped around the local constable until he let one of my shipmates out of the drunk tank. It didn’t figure.

So I’m standing at the bar, wound up tight, waiting on Carlos, and my ears started playing tricks on me. My back was to the table, but I was suddenly sure they knew who I was, that maybe Carlos had clued them in, and they were talking about me. They were talking low, but I caught stray syllables and I swear it sounded like “That’s him,” “Stupid fool.” I even thought I heard “sissy” once. Then the woman started to laugh, long and hard, and it was like a hand on my throat. I couldn’t take it. Half crazy with rage, I roared “Rum!” at Carlos. He stopped pouring and looked at me.

“What’s that, sir?” he said.

“Rum!” I shouted. “Goddamn rum bottle!”

His look turned funny. See, my throat was so tight it probably sounded like I was asking him to rumba around the room with me. Finally I just started jabbing a finger like a goddamned gorilla at a full bottle of Bacardi. It kind of unnerved him. He put aside the drink he was making and came over with the bottle. I grabbed it and two glasses from behind the bar, spun on my heel and marched at the table.

And I say marched at because I was so blind with rage I could barely see. It’s what they call in the old country “bloody-eyed” because it’s like you’re looking through a veil of hot blood. So it was no wonder I bumped into something before I could reach the table.

I was only a couple steps away, but something below me, at about waist level, was blocking my way. I tried to shove past it, but it was solid and heavy, like a rock. I finally looked down and there was that photobug, squinting at me from his chair.

“Pardon me, chum,” he said in a slurry English accent, “but I was here first.”

I looked at him like an idiot and the bullfighter said something in Spanish I didn’t catch and the table really lit up with laughter. Which just made me madder. Every muscle in my body was tensed. The shutterbug I was still trying to walk over asked what he’d said and the woman said in a German accent, “He said the bullish gentleman has mistaken you for a vaca, a cow.”

“Is it true?” the shutterbug said. “Am I being propositioned? I say, are his intentions honorable?”

He went on like that but I wasn’t listening anymore. I’d managed to blink enough blood out of my eyes to fix on the old man across the table, the lion I’d staked out. He seemed to think the whole thing was funny.

“You look familiar,” he said in a low, slow voice.

“My brother,” I choked out. “My brother.” I wanted to explain more, but I couldn’t croak it out, my throat was wound tighter than a ship’s bow line in a hurricane.

“What do you want?” he asked.

“Giustizia,” I said in my father’s voice.

“Approvazione,” Hemingway said in perfect Italian. “Sit down.”

I managed to steer around the shutterbug and sat down. It hadn’t worked out like I’d imagined, that’s for sure. As I said, I’d been sitting there for three days, scheming over rum, letting my imagination run wild. In my mind I’d rehearsed and improved upon the scene until it was perfect. I would storm the table, demand justice, then we’d start laying into the rum. He’d be daunted at first, just looking at me he’d know he was in for a helluva fight, then once he’d got a few drinks in him he’d start getting all mouthy and brave, telling his gang that he’d have me on the floor like Marco in short order. I’d grit my teeth (in some of the early versions I knocked him to the floor with a single punch) and steadily drink him down. Terror would surface in his eyes toward the end, that sickening horror every undefeated boxer gets when he first realizes that the guy he’s in the ring with is better than him, that he’s finally going to taste canvas. Then, when he tumbled out of his chair like a sack of wet cement, I’d make like I was going to pour the rum in his face. Then I’d catch myself, all noble like, and say, “It’d be a waste,” or “Enough good liquor has been wasted on you already,” something like that. Then I’d drink his rum and walk out. It was going to be perfect.

But it wasn’t like that. When I finally sat down, I didn’t feel angry so much as uncomfortable and dumb. I felt like some uppity stevedore who’d barged his way into the captain’s mess and demanded a seat at the table for no good reason at all. I felt like my father.

My father was a very proud man. So proud he spent half his life insulted and the other half plotting revenge. He didn’t speak English very well and he construed everything said to him as a grave insult. A nun could tell him good morning and he’d swear she called him a good-for-nothing wop.

And now I felt just like him, stiff with insults and unable to make myself understood. I tried to talk but my mouth was full of gravel. So instead I filled both glasses with rum and pushed his across the table. He immediately picked it up.

“Salud,” he said.

“Salud,” I said and we knocked them back.

I was pouring before the glasses hit the table. When we were reloaded, I picked up my glass and looked dead at him. He paused, then picked his up. No saluds this time. I belted mine back and pointed the empty end of the glass at him. He did the same.

“I say, is this a game?” the photobug said. “Can I play?”

“No game,” Hemingway said.

“Corrido,” the bullfighter said.

“Eh?” the photobug said. “And whom, may I ask, is the bull?”

Nobody said anything, but everyone at the table knew who was who. It was all wrong, all backwards. I’d set myself up as the heroic hunter out to kill a murderous old lion ,   but he’d tricked me somehow and now I felt like the beast.

“You poured it in his face,” I sort of blurted, right out of the blue. I wasn’t so much accusing him as trying to remind myself that I was the good guy.

“How would he know?” the blond man said. He sounded South African or Rhodesian, and he damned sure knew what I was talking about.

“He was told you poured it on his face,” I said.

The South African started to speak and Hemingway cut him off.

“Pour,” he said.

This is when my memory gets a little hazy. We went on with rum for a while, then suddenly there were all sorts of bottles at the table, his gang was drinking up a storm. Toasts were being raised and there was a lot of fooling around, but I tried to keep the focus in the eye of the storm, whatever Hemingway poured or was poured, I doggedly made sure I got the same. They came in a flurry, mostly foreign stuff — brandies, liqueurs and a lot of grappa.

My stomach started to roll a little and when I reached down to loosen my belt a notch I saw the old man grinning at me. I suddenly realized that the wily sonuvabitch had been working an angle. Like an old boxer who’d lost his knockout punch, he’d bulled in close and went to work on my midsection, he’d been working my body with weird liquors that didn’t mix well.

I made sure we went back to the Bacardi, filling our glasses before anyone else could. I backed him off me with solid rum hooks, but the bottle went dry and he waved over Carlos and whispered in his hear and Carlos came back with a tray of bottles: Gin, whiskey, Pernod, Fernet Branca and a small bottle of bitters. Hemingway started mixing them up right at the table, like he was just experimenting, and they tasted like hell to me. He seemed to like them though, and I realized he was putting together combinations like a boxer puts together punches, trying to knock me off balance.

And it was working. I’m a neat man, and I don’t mean I’m fussy about my clothes. I like my liquor straight up. So did Jumpin' Jimmy Monroe, and that’s how I beat him. But this cagey bastard was unloading the back bar on me and I was backing up. I hadn’t gone to the head yet, so I excused myself. I made sure I got up very slowly and it was a good thing, because my sails were full and I felt a definite list toward portside. I made it to the head fine, emptied my bladder, then looked at myself in the mirror.

I didn’t look so good. I didn’t feel so good. My stomach was at full boil now and I had the look of a journeyman boxer eight rounds deep with a contender. My face was sagging, my eyes looked hollow, except for a little fear. I slapped some cold water in my face and all it did was get me wet.

I was going down and I knew it. If I had a corner man he’d tell me that my only chance was a lucky knock-out punch and he’d be dead right.

When I went back to the table, moving very carefully, I didn’t sit down immediately. Instead I bent down and opened my duffel, and took out my present for Mr. Hemingway.

It was rum, but not just any rum. It was Perro Negro Especial, a smoky, high-proof product of an evil-minded distillery in the Philippines. Not many men like Calvados, I’ve seen weathered sea dogs tremble before it like sheltered virgins. But I’d cut my teeth on it during a two-year stint tramp freighting out of Manila, and I’d built up an immunity, as much as a man could to the stuff.

I watched him very closely when I put the bottle on the table. I’d like to say the old man flinched when he laid eyes on it. I’d like to say a little light went out of his eyes. But it didn’t happen. He just whispered something to the Spaniard. Miguel hefted the bottle and squinted at the label. The rest of the table took notice too.

Carlos came over with a corkscrew. He frowned with disgust when he saw the label ..I noticed the German lady coolly staring at me from over a cigarette, like she’d identified an acquaintance as an assassin. The South African glared, the shutterbug took a picture.

Carlos poured, cursing softly in Spanish as he did so, then walked off. I picked up my glass and so did the old man.

“Vaya al diablo!” he said.

“Vaya al diablo!” I said.

We drank them down. Perro Negro Especial runs about 150 proof, depending upon the batch, and it comes on like a freight train. I mean, it hits you so hard your dead great great grandfather feels it.  

“You like the Black Dog?” I asked him.

“De noche todos los perros son negros,” he said.

Which means, “At night, all dogs are black.” It was pretty tough talk, all right.

I reached for the bottle, and that’s the last thing I remember.

Sometimes I think I can remember pieces of what happened, but most likely it’s my mind working off what Carlos later told me.

He filled me in a couple days after the fact, when I stopped by to say goodbye. He wouldn’t talk to me at first, but he finally came around. He related the story like he was describing something blasphemous and obscene that he’d been forced to take part in.

He didn’t know how many rounds of Black Dog we drank, or who all was drinking it, but most of the bottle was gone when he cleaned up. He said that about half an hour after I brought out the bottle I’d jumped up from the table and grabbed the photobug, like I was going to strangle him. Maybe he said something I didn’t like, I don’t know.

The South African and the matador pulled me off and pinned me on the floor. After a while they let me up and I was acting fine and even laughing a little, then I made a grab at the woman. They wrestled me down again and this time the South African sat on my chest for a long time, slapping my face every now and then. He finally let me up and I bowed to the table, put on one of their hats and said I was heading back to New Orleans to catch a freighter, and we would continue this at the next port. I then walked toward the door, meaning I crashed into a series of tables, then laid one out flat. And that was it, I was out.

“What did Hemingway do all this time?” I asked Carlos.

Carlos shrugged. “He thought it very amusing.”

“How did I get back to my hotel?”

He shrugged. “The African and Miguel carried you out.”

I offered to pay for the table but he refused my money. I had one for the road and left Key West without any hard feelings. The old man had beat me fair and square. I got into the ring with the champ and he floored me. There was nothing to be done about it. Years later, when I read that he’d killed himself, I drank a bottle of Perro Negro in his honor. It was the least I could do.