WHITEHEAD STREET

Nicholas Trandahl
11 min readMay 2, 2020

By Nicholas Trandahl

Jack was full and a little drunk from dinner. He’d just eaten at a little restaurant on Duval Street, and his meal had been a couple big conch tacos and a few bottles of citrus beer from a brewery right there in the Keys, up north in Islamorada. His dinner done, Jack strolled through the nighttime crowds along Duval.

The smiling faces that passed by on the sidewalk were fresh college-aged faces, withered old faces, and middle-aged faces like Jack’s own. The nocturnal people of Key West seemed to be made up of every sort of character, and all these characters made their way to the southernmost point in the United States, the terminus of U.S. Route 1, to lose themselves … or to find themselves.

Key West was, in a way, the furthest fringe of American civilization, and despite the island’s grand hotels, expensive food, and idyllic tropical climate, it kept the gritty essence of a rough frontier town. It was a bikini-clad backwoods paradise that swarmed with iguanas, chickens, burn-outs, Cubans, and East Coast upper class tourists. Jack had no idea where exactly he fit in among the Key West set, but he nonetheless found himself there on vacation.

Jack was down on the island for the same reason as most — the sun, the sea, the nightlife, and the anonymity. His recent divorce, his second, had stripped his bank account of pretty much everything. Jack had taken most of what was left to fly to Key West for a little vacation and rent out someone’s little bungalow for five days. It was nerve-wracking for Jack to be in such a financial situation in his mid-forties, but he thought, Screw it. I’ll just start over from square one when I get back home.

I’ll learn how to live again.

As he sauntered down the crowded sidewalk in the warm night air, Jack stopped to buy a slice of Key lime pie from a Cuban that sold them from a wheeled cart. A few cars crept down the brightly lit streets that swarmed with pedestrians, but most of the traffic consisted of bicycle-borne rickshaws or old-fashioned pastel-colored cruiser bikes that tourists could rent. The bikes even had baskets on the handlebars.

Jack stood on the sidewalk near the pie cart. As he devoured the frosty slice of tart pie, he watched the people and the bikes. When he finished his slice of pie, he tossed the small paper plate and plastic fork it had been served with into an overloaded public trash can that was chained to a light pole. Before he wandered off into the night, Jack took out a cigarette. He put it between his lips, which were still cool from the cold slice of Key lime pie, and he lit it with his lighter.

“Wanna get a picture with me, buddy?”

Jack turned towards the gravelly voice and saw a stocky older man in black leather vest, cargo shorts, and sandals. A shabby purple bandana covered the man’s head. His white-whiskered face and tattooed arms were deeply tanned by the south Florida sun. The man, a pirate reenactor, obviously plied his trade among the intoxicated upper class tourists and vacationing college students in downtown Key West, taking a fee for tourists to take a photo with him so that back home they could show their stuffy friends how they’d met a real-life pirate in the Keys.

Jack thought the man looked like a subpar or inauthentic pirate reenactor with his modern shorts and sandals. However, these shortfalls were made up for by an actual living parrot that perched massively on the man’s shoulder. The big tropical bird was blue, but its feathers were grizzled and dirty. It looked like the avian version of its owner.

Jack smirked around his cigarette and answered, “No thanks, matey. Nice bird though.”

“Nah, she’s an asshole,” returned the pirate. “She can be one mean bitch.”

“Sounds like my ex-wife,” Jack returned with a grin.

“Mine too.”

They shared a laugh, and Jack continued to smoke his cigarette. The pirate hovered nearby and watched the crowds. The parrot gnawed on the unkempt feathers of its own blue back.

“Could I bum a smoke?” the pirate finally inquired in his ragged voice.

It sounded to Jack like the last thing the pirate reenactor needed was another cigarette, but it was a free country. Any man was free to offer himself up as a sacrifice to his vices. “Sure,” Jack answered.

He handed the pirate a cigarette and lit it for him. The man with the parrot drew deeply from the cigarette. The ember shone hot and orange in the night, and it crackled softly as the man sucked on it. The pirate sighed out a big mouthful of smoke, bloodshot eyes closed with contentment.

No mercy is ever too simple, thought Jack as he watched the man savor the cigarette. No mercy is ever too small.

They stood smoking in silence, the strange pair, as the nocturnal horde of tourists moved by. Finally, the pirate asked in his rough voice, “Where are you from? I can tell you’re a tourist.”

“Is it that obvious?”

“Yeah,” the pirate laughed.

“I’m from north of here,” Jack quipped with a slight grin that the other man’s weary eyes barely noticed. Since Key West was the southernmost point in the United States, anywhere else in the country was considered north of there.

The grizzled pirate reenactor snorted through his crooked nose. The parrot made a hissing noise. Then the man asked, “Have you went to the Hemingway House yet? It’s closed now, but you should check it out if you haven’t gone yet.”

“I haven’t. I’ll have a look around tomorrow. I haven’t read any of his work in a long time.”

The pirate explained, “Well, it’s just over on Whitehead Street. I love his stories, especially To Have and Have Not. It takes place here in Key West, you know. He wrote most of his work when he lived here. You can buy one of his books at the gift shop.”

“Will do, buddy. Hey, I’m going to take off. You have yourself a good one,” said Jack.

“You too. Be good. Thanks for the smoke.”

Jack continued down the sidewalk along Duval Street. The weathered pirate reenactor and his rough-looking blue parrot were left behind. He had nowhere specific to go, and he certainly wasn’t ready to head back to the little bungalow he was renting during his vacation. So, Jack ducked into a busy bar.

The noise and the jostling bodies of the clientele were oppressive to him, and his loneliness and isolation became clearer. However, he wasn’t depressed about it. He cloaked himself in his facelessness and solitude. He listened to the barely discernable sound of the Beach Boys over the cacophony of conversation, shouts, and laughter. Jack imagined that he was the only person in the bar at that hour that listened to the music.

Smiling to himself, Jack quickly downed two tumblers of dark spiced rum. The rich liquor hit him quickly, and he was profoundly drunk when he walked uneasily out of the bar a little later. He hadn’t spoken to another soul besides the bartender the entire time he’d been in the bar, and he’d spoken with the bartender only to order his rum.

Jack had a faint awareness that he was grinning drunkenly as he continued his saunter down Duval. He knew he’d be an easy mark for a thief, but he didn’t really care at that point. A carefree realization had settled on him. He had nothing left for someone to take. He had nothing to worry about. What further damage could a thief do to him that his ex-wife’s divorce attorney hadn’t done?

Jack turned left and walked down Olivia Street. After walking for a block, he took another left and found himself on Whitehead Street. Whitehead was much less busy than Duval and, to Jack, there even seemed to be less streetlights. In his intoxicated numbness, he hadn’t meant to go to Whitehead Street, but he also didn’t feel like the hands of the universe or God had taken him there. Jack didn’t believe in fate, especially after true love had turned to bitterness and animosity twice in his life. He believed in chance, and he drunkenly chalked it up to chance that he’d staggered onto Whitehead Street.

The Hemingway House wasn’t hard to find. It was on the corner of Olivia and Whitehead, the highest spot of the crowded island and across the street from the towering white edifice that was the Key West Lighthouse. Jack found himself right next the dark brick wall that encircled the Hemingway property. The big square house and the palm trees around it loomed dark beyond the wall in the dim ghostly light of the crescent moon. Jack reached out his hand as he walked and trailed his fingers along the coarse bricks.

He followed the wall along the front of property, along Whitehead Street, until he neared the closed entrance of the Hemingway House. He sighed and leaned his back against the wall, and he slid down so that he sat on the sidewalk. Jack’s head swam, and his world tilted precariously. He passed out, but only for a moment.

Jack snorted through his nose and jolted awake. The white crescent moon was still suspended in the clear night sky above. He glanced in both directions down Whitehead Street, and he was confused to see the street suddenly emptied of any nocturnal pedestrians or revelers. The streetlights that lined the sidewalks seemed somehow dimmer and fewer in number than they had been moments before.

Then Jack thought of Ernest Hemingway. He didn’t think he’d ever thought about the prolific 20th century American author. Jack wasn’t a writer himself and he was no great reader. He had never been interested in Hemingway, but he had read somewhere that the author had been married several times before he killed himself.

Jack asked out loud, “Ernest, why do we do it? We do we keep tying ourselves to people that destroy us?”

There was no answer other than the muffled nighttime sounds of Key West — the distant shouts, the wind in the palm fronds, and the cries of the unseen gulls that rode the darkness like seaborne devils. Suddenly, the sounds of the island stopped. They didn’t fade away; they simply ceased. The only sound Jack could hear was the beating of his own heart in his ears.

Jack hadn’t expected an answer, but then there was one. It came from the darkness behind the wall, and even further than that. It was as though it came to Jack from a very great distance, an incomprehensible distance. The man’s voice was peculiar, and it wasn’t a deep voice. It was a voice he’d never heard, but its words were true and sure.

The voice answered, “We do it because we are all destroyed in the end, in one way or another. It is better to love what destroys us — who destroys us.”

Jack sat on the sidewalk, his back against the brick wall. He was silent, confused, and frightened. He’d heard somewhere that Key West used to be an open air graveyard for the indigenous people that lived in the Keys before Europeans came centuries ago. When the first Spaniards landed on what was then known as Cayo Hueso, they discovered the island shrouded in the bones of the dead. After hearing that bit of history, Jack imagined the spirits on Key West were not so far away from the living. The disembodied voice that spoke in the warm quiet night made the hair on Jack’s neck and forearms stand on end.

“Are you …,” Jack began, but he found it difficult to say the name, to utter the absurd impossibility.

“I am,” the voice answered. “That is … I was.”

Jack was silent again. His head swam, both from the alcohol and from the bewildering conversation he’d suddenly found himself in. “How am I talking to you?” he asked anxiously.

The voice answered, “Does it matter? Our time is limited. Do you want to waste that time on questions that won’t matter in the end?”

“I don’t know what I’m doing,” Jack desperately confessed. Tears rushed unbidden from his eyes. “This second divorce has ruined me. I loved her. I swear I loved her. But now I’m completely destroyed.”

“A man can be destroyed but not defeated,” the voice replied.

The quote sounded familiar to Jack. He was sure he’d heard or read it somewhere, but he’d forgotten where. The words and the voice that spoke them gave Jack a sort of strength. He wiped the tears from his eyes.

The voice beyond the wall continued, “I had three divorces, and each one of them broke me to pieces. But the world breaks everyone, kid. I am no different than you or from anyone else. We all suffer for love.”

Jack was dizzy. The bricks were hard against Jack’s back, and the sidewalk was hard against his bottom. His legs were sprawled out in front of him, his feet close to the gutter. Whitehead Street was still empty except for two souls, Jack and the voice on the other side of the wall.

“What now?” Jack finally asked into the night. “What in the hell do I do now?”

Jack didn’t recall an answer from the voice beyond the wall, but he heard a different voice from beyond a strange sleepy fog. It said, “Wake up.”

A hand was on Jack’s shoulder, and it shook him into wakefulness. “Hey, buddy, wake up,” the voice, clearer and closer, continued in its gravelly and vaguely familiar character.

Jack’s heavy eyes fluttered open, and in the dim grey light just prior to dawn, he saw the shadowed face of the pirate reenactor from Duval Street. The silhouette of the man’s grizzled parrot was perched on a dark shoulder. His hand still on Jack, the man said, “I had a feeling I’d find you here. You’re lucky a cop didn’t see you passed out here on the sidewalk. Come on, buddy. Get up.”

The night was fading, and the crescent moon had fallen beyond the horizon. Jack knew that several hours had passed since he’d wandered onto Whitehead Street. Jack had fallen asleep on the sidewalk, his back against the brick wall and his legs stretched out. The realization that the voice beyond the wall was most likely just a dream settled suddenly and bitterly on Jack.

The pirate helped Jack to his unsteady feet as the parrot flapped its wings with irritation and squawked loudly. “Can you get back to your place alright, buddy?” the man inquired in his rough voice.

Jack nodded and answered, “Yeah, I’m good. Thanks for getting me up.”

“Drank too much, eh?”

“Yeah, I guess,” Jack answered in a thick sleepy voice. He still felt only partially present. A part of him still spoke to the voice beyond the wall, under the silver shard of moon that had vanished somewhere as morning neared. It had all gone by so quickly, and that distant voice still echoed around in his skull.

“A man can be destroyed but not defeated,” Jack mumbled groggily.

“What’s that, buddy? I couldn’t hear you.”

“Oh, nothing,” Jack replied. “Thanks again.”

Jack marched off down the sidewalk. The pirate reenactor yawned as he stood there and watched Jack sway and brace himself occasionally on the brick wall that encircled the Hemingway House. It was obvious that the vacationer was still drunk.

“Goddamn tourist,” muttered the pirate as Jack made his way down Whitehead Street. The parrot on his shoulder fluffed up its dingy blue feathers.

Beyond the streetlights and the shadowed palms, the grey sky took on a slight blush of pink and yellow. A new day was about to dawn.

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Nicholas Trandahl

Wyoming poet. Published by the New York Quarterly, James Dickey Review, and High Plains Register. Recipient of the 2019 Wyoming Writers Milestone Award.