Hemingway’s Last Tournament: The Old Man and Self-Doubt

The bar at Sloppy Joe’s was thick with smoke and the kind of heat that made your shirt stick to your back even at ten in the morning. Ernest sat at his usual spot, the corner stool where he could watch the door and the street beyond. The daiquiri in front of him was his second, but who was counting? The ice had melted into pale green water that tasted like disappointment.

He’d been sitting there since eight, staring at the typewriter page he’d folded and stuck in his shirt pocket. Fifteen words. That’s all he’d managed yesterday. Fifteen goddamn words, and half of them were “the.”

The young man walked in like he owned the place, which irritated Ernest immediately. He was maybe twenty-five, with that eager look of someone who hadn’t been kicked in the teeth by life enough times. His hair was perfectly combed, his shirt pressed. He looked like he’d never sweated through a shirt or bled on a page.

“You’re Hemingway,” the kid said. Not a question.

“I am.” Ernest didn’t look up from his drink.

“I’m Danny Morrison. I write for—”

“I don’t care who you write for.”

But Danny slid onto the next stool anyway. He ordered a beer, which was smart. The bartender, Carlos, nodded approvingly. Carlos had strong opinions about men who ordered fancy drinks before noon.

“I read your new story in Atlantic,” Danny said.

Ernest’s hand tightened on his glass. The story Danny meant was “The Last Good Country,” and it was shit. Ernest knew it was shit, the editor knew it was shit, and apparently this kid knew it too.

“And?”

“It wasn’t your best work.”

The bar went quiet. Not actually quiet—the fan still wheezed overhead, the radio still played Cuban music in the corner, and the fishermen at the far table still argued about bait. But something in the air shifted, like the moment before a storm hits.

Ernest turned to look at Danny properly for the first time. The kid’s eyes were steady, not challenging exactly, but not backing down either. There was something familiar about that look. Ernest had seen it in mirrors, a long time ago.

“What makes you think you know my best work from my worst?”

“Because I’ve read everything you’ve ever published. Twice.”

“Then you’ve wasted a lot of time.”

Danny smiled, and it wasn’t the smile Ernest expected. It wasn’t cocky or nervous. It was sad.

“You don’t believe that,” Danny said.

“Don’t tell me what I believe, kid.”

“Then don’t act like a has-been when you’re not.”

The words hung between them like a challenge. Ernest could have gotten up and walked out. Could have thrown his drink in the kid’s face. Could have done any number of things that would have ended this conversation before it really started. Instead, he found himself curious.

“You think you know me?”

“I know your work. And I know what it’s like to sit at a typewriter and feel like a fraud.”

Ernest laughed, but it came out bitter. “You’re twenty-five. What the hell do you know about being a fraud?”

“More than you might think.” Danny took a long pull from his beer. “You want to know what I did yesterday? I wrote three thousand words. Good words. Real words. Words that said something true about what it means to be alive. Then I read them over and threw them all away.”

“Why?”

“Because they sounded like you.”

Ernest studied the kid’s face. There was no accusation there, no blame. Just a statement of fact.

“That’s not necessarily a bad thing,” Ernest said, though the words felt strange in his mouth.

“It is if you’re not you.”

They sat in silence for a while. Carlos refilled Ernest’s daiquiri without being asked. The fishermen settled their argument and left, trailing the smell of salt and diesel fuel. New customers trickled in—tourists mostly, loud and obvious in their vacation clothes.

“I’ve been writing for thirty years,” Ernest said finally.

“I know.”

“Won won a Pulitzer. A Nobel Prize.”

“I know that too.”

“And yesterday I wrote fifteen words and they were all garbage.”

Danny nodded like this made perfect sense. Like it was the most natural thing in the world for Ernest Hemingway to sit in a bar confessing his failures to a stranger.

“What were the fifteen words?” Danny asked.

Ernest pulled the folded paper from his pocket. He’d been carrying it around like evidence of his own inadequacy. He smoothed it out on the bar.

The woman walked into the hotel bar and ordered whiskey like medicine.

Danny read it twice, his lips moving slightly. Then he looked up at Ernest with something that might have been awe.

“That’s not garbage.”

“It’s obvious. Heavy-handed. A child could have written it.”

“No,” Danny said quietly. “A child couldn’t have written it. Neither could I. And neither could most of the writers getting published these days.”

Ernest wanted to argue, but something in Danny’s voice stopped him. There was a quality there he recognized—the sound of someone who’d spent enough time with words to know their weight.

“You want to know what I think?” Danny continued. “I think you’re scared.”

“Of what?”

“Of not being as good as you used to be. Of writing something that doesn’t live up to the Ernest Hemingway brand.” Danny gestured at the bar around them, at the tourists who kept glancing over and whispering. “Of being mortal.”

Ernest felt something hot and angry rise in his chest. “You don’t know what you’re talking about.”

“Don’t I? You wrote For Whom the Bell Tolls twenty years ago. You wrote The Old Man and the Sea fifteen years ago. And every day since then, you’ve been trying to write something that good again. Every story gets measured against those. Every sentence. Every word.”

“That’s what writers do. We try to get better.”

“No,” Danny said. “That’s what scared writers do. Good writers just try to tell the truth.”

He pulled out a notebook, worn and coffee-stained, and flipped through pages covered in cramped handwriting. “You want to see something? This is from yesterday, before I threw it all away.”

He found the page he was looking for and read: “The young man sat at the typewriter and felt the weight of every great book ever written pressing down on his shoulders like stones.

Ernest recognized the rhythm, the deliberate simplicity that masked complexity. It was good. It was also unmistakably influenced by his own style, but there was something else there too—something uniquely Danny.

“Why did you throw it away?” Ernest asked.

“Because it sounded too much like Hemingway. Because I was afraid people would say I was copying you. Because I was afraid you would read it and think I was copying you.”

Ernest looked at his daiquiri. The ice had melted completely now, diluting the rum until it was barely colored water.

“Can I tell you something?” he said. “When I wrote The Sun Also Rises, I was terrified it was just a cheap imitation of Gertrude Stein. When I wrote A Farewell to Arms, I was sure everyone would say I was trying to be Stephen Crane. And when I wrote For Whom the Bell Tolls, I spent half my time convinced I was a pretentious ass who had no business writing about war or Spain or anything else.”

Danny stared at him. “Really?”

“Really. You think the Nobel Prize committee calls you up and says, ‘Congratulations, you’re officially a real writer now, you can stop doubting yourself’? Hell, no. If anything, it makes it worse. Now everyone expects you to be Ernest Hemingway all the time. Even when you’re just a guy from Oak Park who happens to know how to string words together.”

Ernest pulled out his own notebook and wrote something quickly. He tore out the page and handed it to Danny.

The truth was this: every writer was a fake until the moment they stopped pretending to be anyone else.

Danny read it and looked up. “Is that for your story?”

“No,” Ernest said. “It’s for yours.”

They finished their drinks in companionable silence. The bar filled with the lunch crowd—locals who nodded at Ernest but didn’t bother him, tourists who pointed but kept their distance. The normal rhythm of a Key West afternoon.

Finally, Danny stood up and left money on the bar. “Thank you,” he said.

“For what?”

“For reminding me that even Ernest Hemingway used to be just Ernest.”

After Danny left, Ernest sat alone for another hour. He thought about the fifteen words on the crumpled paper. The woman walked into the hotel bar and ordered whiskey like medicine. They weren’t garbage. They were the beginning of something true.

He walked home through streets that smelled like fish and jasmine, past houses where bougainvillea climbed over fences and cats dozed in the shade. At his typewriter, he rolled in a fresh sheet of paper.

The woman walked into the hotel bar and ordered whiskey like medicine. She had news to deliver and no good way to say it.

The words came easier after that. Not because he’d stopped being afraid of failure, but because he’d remembered something more important: the fear meant he still cared. And caring, even when it hurt, was what separated the real writers from the ones who were just playing dress-up.

By evening, he had two pages. Good pages. Not perfect pages, but honest ones. Pages that sounded like Ernest Hemingway not because he was trying to imitate himself, but because he was trying to tell the truth.

That night, Carlos found him still at his corner stool, but this time he was writing in his notebook instead of staring at his drink.

“Good day?” Carlos asked.

Ernest looked up from his work. “Getting better.”

“That young man who was here earlier—he came back looking for you.”

“What did you tell him?”

“That you went home to write.” Carlos grinned. “He said that was the best news he’d heard all day.”

Ernest smiled back. Outside, the Key West sunset painted the sky in shades of pink and orange that no writer had ever adequately captured, though God knew they’d all tried. Tomorrow he would try too, and probably fail, and probably try again the day after that.

But tonight, he had two pages of honest work and the knowledge that even fear could be a kind of fuel if you learned how to burn it properly.

The truth was simple: there was no such thing as a real writer, only writers who kept writing despite feeling fake. The secret wasn’t conquering the doubt. The secret was making friends with it, inviting it to sit at the bar next to you, and buying it a drink while you worked.

After all, everyone felt like an imposter sometimes. The trick was showing up anyway.

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