A Grimm Night on Central Park South
An Original Dark Fiction Office Fable for Halloween
Hey friends,
This week’s newsletter is a little different. Since it’s Halloween, I wrote you a short story based around the NYC tech scene and a billionaire’s eerie penthouse. I hope you enjoy this small dose of dark fiction—perfect for the season—and let me know what you think of this creative detour before we return to our more regular programming. As always, your feedback is greatly appreciated and don’t forget to subscribe and share!
In the elevator ride to the fiftieth floor, Alayna tied and untied the knot of her Red Riding Hood costume for the sixth, maybe seventh, time.
It was her first Halloween party with this new company, and after finally pulling herself away from the mirror in her Flatbush apartment and barreling through a subway full of Jokers, Demon Hunters, and life-sized Labubus, she was grateful to have a moment to decompress.
The party was in the CEO’s “apartment”—which was really a five-floor penthouse—on top of one of the most iconic buildings on Central Park South. A few years ago, after the purchase was announced, every news outlet in America had reported on the change in ownership:
“Tech CEO Bryce Granger Adds Apartment Overlooking Central Park To Expansive Real-Estate Portfolio”
The coverage was less about real estate and more about the explosive rise in Granger’s profile. Although well-known in Silicon Valley, Granger had managed to fly under the radar of public perception for most of his career. But with LLMs becoming as commonplace as coffee-makers—and the company he founded, Lupine Labs, being the number one provider of cloud-based infrastructure to Big Tech companies—Granger’s net worth had skyrocketed.
Of course, Alayna didn’t know any of this back then. She was only half sure that she understood it now. She had been an English major in undergrad and, to the immense frustration of her parents, went back to earn an MA in German Literature and Translation. Transformer models, neural networks, and data lakes weren’t exactly topics she stumbled across when interpreting Goethe.
But after graduation, while her friends became more established in their respective careers, Alayna became more and more desperate for a job. She had received multiple offers early on, but her success had made her overconfident. She turned them all down, convincing herself that the perfect offer would come. It never did—and eventually the offers stopped coming entirely.
“I don’t know. I’m going to reach the end of my savings soon. Plus—the pause on my student loan repayments is about to expire,” Alayna had bemoaned to her friend while facedown on the sofa.
“I’m telling you. I can get you that job at Lupine. They’re looking for a language nerd and you are, like, literally the only person I know that has studied phallusology,” Mina replied.
“It’s phil-ol-og-y,” Alayna shot back, making sure to over-annunciate the four syllables. “Phallusology sounds disgusting.”
Even with her head buried in the couch, Alayna could hear Mina giggling from the corner. Realizing that her friend had intentionally butchered the term, Alayna chucked a pillow in the direction of the laughter.
“Ha! Missed me!” Mina teased triumphantly.
Mina had a knack for pulling Alayna out of her funks. She was the only one of Alayna’s friends that wasn’t trying to be an artist and she had essentially networked her way into a job as HR at Lupine right out of business school.
“For real though. They need someone with a background in language to fine-tune a model they’re prototyping. The salary is insane, plus it comes with equity. I could put in a good word for you. You can get a job that actually uses your degree!”
“Mina, I’ve told you before. I don’t want to use my degree to make some AI slop machine. I want to work with real literature, with real books,” replied Alayna, with just a hint of intentional dramaticism.
“I know, I know. But maybe you’re thinking about it wrong. These models are the future. One day we won’t need translators because AI is going to do it for us. It will only become slop if shitty people do a shitty job. That’s why YOU should do it. You care.”
“AI can’t do what I do. Translation is more than just knowing languages and punctuation. You have to understand context, history, emotions. You have to know what the words feel like in your mouth. AI can’t do that.”
“Yeah, that’s what you say now, but things change. It’s just like the thing that turned you into a Germanophile— what was it? The Glutenberg machine? I bet a lot of people hated that when it was invented.”
Alayna lifted her head from the couch but paused before responding. She wasn’t sure whether Mina was baiting her by saying Glutenberg instead of Gutenberg, but either way, Mina’s words had struck a chord.
“The printing press did polarize people,” she said out loud but mostly to herself. “People thought that it would cheapen knowledge and make everyone stupider. In reality, it democratized knowledge and paved the path for modernity.”
Alayna would never admit it, but that moment was the turning point in her decision. Just a few days later she submitted a resume to Lupine Labs and asked Mina to pull some strings.
“But it is only temporary!” Alayna insisted. “Someone else is going to do it if I don’t, so I might as well pay bills until I can find something else. And I’m not going to let it turn me into some cringey girl boss – I’m keeping my soul, thank you very much.”
Indeed, Alayna’s costume was one of the small ways she asserted her individuality and resisted the milieu of corporate life. At least, that’s what she told herself. Dressing as a character from the Grimm Brothers—who were also philologists—was a small, secret nod to her true passion and a reminder that a little detour didn’t necessarily mean permanent derailment.
The elevator doors opened into a hallway that seemed more like a museum than a living space.
There were no visible decorations, furniture, or decor. Just massive white arches brooding over marble floors like stone trees in a terrible, monochrome forest. If not for the music and lights coming from the end of the hall, she would have turned around and gone home.
The rest of the first floor, however, was common enough—at least, common for a penthouse— and the party was relatively banal. As part of the HR team, Mina was busy playing adjunct event manager for the evening, buzzing around the different rooms and social circles.
“Parties are nightmares for HR employees,” Mina explained to Alayna over the blaring “Thriller” soundtrack. “Especially parties with alcohol. But the culture-setting and ego boost of partying at a billionaire’s penthouse outweighs the risks, I guess. Whatever— I’d rather be on Halloween duty than have to work through the Christmas party anyhow. And if something does happen, it’s not my funeral.”
Mina’s intermittent absence throughout the evening forced Alayna to make more small talk than she would have preferred, but after a while, she didn’t mind. Besides the few oddballs obsessed with talking about “the imminent singularity,” everyone seemed chill—friendly, even.
“Maybe the people here aren’t monsters after all,” Alayna thought to herself. Her contemplation was interrupted by Mina who came up behind her.
“Gaaawd, I swear, people have zero common sense. Apparently, one of the interns is here. This was supposed to be invite only—for hired staff. And if that’s not enough, now they’re getting a little too friendly with their married manager. Did people learn nothing from the Colplay fiasco? Now I have to find a way to tastefully intervene ASAP, but the DJ is threatening to stop playing unless he’s paid and I think I left the check upstairs.”
“I can get the check!” offered Alayna.
“Oh, are you sure? That would actually be so useful, but I don’t want you to miss the party.”
“I don’t mind!”
“Okay, great. It’s, like, on the third or fourth floor. Right outside the elevator on the hallway table where the mail goes. You can’t miss it!” shouted Mina, who was already seven paces away.
“Not exactly GPS coordinates, but I guess it will do,” thought Alayna.
To her dismay, there were no tables in the third floor hallway. There were no tables on the fourth floor either. Not wanting to go back empty handed, she decided to quickly check the fifth floor. Back in the elevator, she again retied the crimson strings beneath her chin.
The doors opened to a brightly lit room and Alayna took a step inside.
“Hello?” a voice sang from the opposite side of the room and startled Alayna. It was a man’s voice. When she turned around, Alayna saw that it was the CEO himself. She was a bit stunned, but managed to keep her composure.
“I’m sorry, I didn’t mean to interrupt you,” Alayna said. “I was looking for something for the party and when I didn’t find it, I wanted to check here. My bad.”
With that, Alayna turned around to get back in the elevator, but only in time to see it close in front of her. As the colored numbers on top of the door frame descended lower and lower, so did her heart. She was now stuck awkwardly on the wrong floor with her billionaire boss.
“Oopsies. That’ll take a moment to come back. What were you looking for? And, I apologize, but you work for me, right?” Granger asked while stepping a bit closer.
“Yes, I do. And, uh, it was the check for the DJ,” Alayna responded while swallowing her spit.
This was her first time meeting Granger and she was startled by how different he looked in person compared to podcasts. He was always strange-looking, but it was worse in person. He had thin, wiry lips and his clay-like skin made him look both impossibly old and strangely young at the same time. His head was just a bit too small for his body, and the enormous shoulder pads in the suits he wore exaggerated the disproportion. The way his expression had changed from welcoming to curious seemed unnatural. It reminded Alayna of the way an app refreshes, offering something in order to be accepted and hold attention.
“Sure,” said Granger. “I wonder if it didn’t get collected with some of the documents I had placed on my desk. I was just going to get those anyway. Let’s check.”
And with that, Granger unlocked a door leading to the next room and gestured for Alayna to enter. The room was dim and Alayna could only make out shapes on the other side.
“Are those sculptures?” she thought.
Noticing her hesitation, or perhaps impatient with her slowness, Granger explained.
“This is my collection room. I’m a collector. I just had a new piece arrive today, in fact. But with the party taking place, I didn’t have time to review the purchase agreement and letter of advice, which I’m eager to attend to. Come on in. It’s not everyday I get to inflict my hobby on someone new.”
Once inside the doorway, Alayna stood still, afraid to move lest she knock over one of the sculptures by fumbling around in the dark. Granger walked confidently to the corner and turned up the dimmer lights. To Alayna’s alarm, the shapes were not sculptures at all.
Instead, the room was full of every kind of macabre invention and torturous device imaginable. As she scanned the expansive open floor, she could see that every square foot contained a new horror from another century of ancient history. Guillotines and gurneys with leather binds; breaking wheels and rope pulleys; Judas Cradles and crucifixes; ovens with locks on the outside and Brazen Bulls with scorch marks; crude instruments with snagged edges casting ugly shadows on the penthouse wall. A sense of disgust flooded over her and it took all her focus not to vomit on the marble floor.
“They are, as I’m sure you guessed, instruments of death. Death and torture, to be exact. Some are used, but most aren’t. Or, at least, it’s impossible to know whether or not they’ve been used. I have commissioned a replica or two, but I prefer to buy the real thing. Also, I try to buy widely in a geographical sense. Diversity is a value for me, you will remember. Those dinner knives, for instance, came directly from a tribe of cannibals in South America. Dinner knives. Get it? Oh—and that seemingly innocuous bucket? It was used by the mafia once when one of their family members turned out to be an informant. They filled it with rats then placed it upside down on the informant’s stomach and heated it. With no other escape, the rats gnawed through their family member’s body to escape. Gruesome, isn’t it? But you have to admit that there is a certain poetry in killing a rat via actual rats. It’s destructive, sure, but it’s also creative. Schumpeter had a term for that. Nowadays, people bowdlerize those kinds of terms in order to make them more palatable. Take business strategy, for instance. I hate that term. There is no such thing as business strategy. All of it comes from the military. That’s right. The only thing that an executive knows about strategy comes from death— that’s why competition in the markets isn’t for everyone. And technological progress? You’re looking at it. Tech advancement has, and always will be, driven by people with political purposes when they have a vision for the future, which means the current reality has to die. In other words, people are only innovative when they have an impulse to be devastating. If you don’t have that killer instinct, you’ll never do anything great, don’t you agree? That’s why I come in here to ponder all my big decisions. I get all my best ideas right in this room. Now, where are those documents?”
At this point, Alayna no longer needed to vomit because she was almost entirely disassociated from her body and was quite sure that she had wandered into a dream. The surrealness of the situation— the penthouse with its view and the billionaire with his disgusting shop of horrors—had erased her sense of location entirely. Yet the sudden awareness that Granger was standing in front of her snapped her back to reality. He was holding an unopened envelope by his side and offering her a piece of paper with the other hand. It was the check.
Alayna, careful not to seem too hurried, reached for the check, but at the last second Granger pulled it back.
“Ah, but wait, I didn’t even show you my newest acquisition. It’s a real work of art. Very unique. It has all the hallmarks of traditional torment but with a twist. Let me show you.”
The apparatus, to Alayna’s eyes, was nothing short of an abomination. It had the appearance of a skeleton roughly five feet tall, fashioned in brownish copper, but with six bony arms extended and protruding from it’s back. At the end of each arm were eldritch-looking axes with sharpened blades.
Granger looked at the grotesque figure with indifference, but something in his eyes betrayed his admiration.
“Have you ever seen anything like it? Of course you haven’t. It’s made of copper, see? But the makers call it “The Iron Woodsman.” And you see those various buttons on it’s chest? The victim would be restrained while standing in front, but given one hand with which they were free to press a button. Each button causes an arm to swing one of the axes—but the victim has no idea which one! Sometimes nothing would happen at all. It’s very psychological. Stochastically induced dread is the worst type of dread, don’t you agree?”
With this last statement, Granger approached the Iron Woodsman and patted it on the head. Feeling queasy again at the sight of the billionaire and his heinous treasure, Alayna turned around. At that very moment, there was a faint pop, no louder than the opening of a soda can. Alayna spun just in time to see the bottom-most arm of the vile contraption spring violently upward and into Granger’s lower abdomen. She leapt across the room to come and aid, but the axe only traveled further along it’s terrible trajectory, ripping a hole from the bottom of Granger’s stomach to midway through his sternum. The angle of the axe lodged in his ribcage and the sturdiness of the statue held his body upright, even as the blood poured from the wound and the last of the light left his eyes. The card which he had been holding fell from his hand and glided towards Alayna.
For reasons she could never explain, Alayna reached down and picked it up. It was the purchase agreement and letter of advice. With trembling fingers, Alayna undid the seal and read aloud:
Dear valued customer,
Thank you for your purchase. We are grateful that there are still connoisseurs like yourself who appreciate the rich subtleties of technology such as “The Iron Woodsman.” Please note that this piece has been restored to full functionality and extreme caution should be exercised when moving or touching the product. As previously stated in our agreement, our company shall not be liable for any damages, losses, or defects arising after the product has been received. If you have any questions, please do not hesitate to reach out to us through your usual sales rep.
Happy Halloween!
Machen Refurbishment Co.
Alayna dropped the letter and screamed.
Feathers For The Footnotes (Bonus Links)
About the Author
Bradley Andrews is a hopeful rabble-rouser on a mission to inspire the world. Stay in touch with what he’s doing outside of Mercury’s Playbook by subscribing to a weekly digest of his activity through micro.blog. This will send you writing, photos, and other curiosities that extend beyond the scope of this newsletter.
Loved the story Bradley - keep it coming. It was both creepy and delightful reading :)
Eerie developments after a solid foundation, solid read!