Every morning, like clockwork, the CEO of one of Manhattan’s biggest banks would descend from his ivory tower—a 52-floor monument to capitalism and expensive coffee—to the bustling sidewalk below. Rain or shine, polar vortex or pigeon parade, there was always one man who greeted him with a grin wider than his shoeshine kit: Eddie, the shoeshine guy.
Eddie wasn’t your average shoeshiner. Sure, he wore the classic vest and bowtie combo like he walked off the set of a 1940s Broadway musical, but his real talent was talking. Fast, funny, and full of theories, Eddie treated every shoe like a confessional. People didn’t just walk away with polished loafers—they left with existential questions, unsolicited relationship advice, and at least one conspiracy theory about oat milk.
But our story begins on a seemingly ordinary Tuesday. The CEO—let’s call him Mr. Carlton H. Brewster III, because of course—stepped out of his town car, unfolded his copy of the Wall Street Journal like it was a sacred scroll, and lowered himself into Eddie’s chair like royalty about to be de-dusted.
“Morning, Eddie,” Brewster mumbled from behind his paper.
“Morning, Mr. B.,” Eddie chirped. “Dow’s down, your tie’s louder than my Aunt Gloria’s karaoke night, and I had a dream last night that pigeons took over the stock exchange. What’s new with you?”
“Earnings reports,” Brewster sighed. “Board meetings. Possible global financial collapse. You know. Tuesday stuff.”
Eddie didn’t miss a beat. “You want the deluxe polish or the ‘please distract me from the crushing weight of capitalism’ shine?”
“Whichever one includes buffing the regret off my leather Oxfords.”
And so began their usual five-minute morning routine: silence from Brewster, sass from Eddie, and a world of high finance meeting a world of high-quality shoe polish. But today, something changed.
Eddie paused mid-polish, frowned, and squinted up at Brewster.
“Mr. B., have you ever wondered if maybe… just maybe… you’re not the smartest guy on the block?”
Brewster blinked. “Excuse me?”
“Let’s say,” Eddie continued, twirling his polishing rag like a magician with a trick up his sleeve, “there’s a man—an average man—who shines shoes for a living. He’s got no MBA, no offshore accounts, and he thinks ‘private equity’ is a fancy term for a velvet rope at a nightclub.”
“And?”
“And this man, who you see every day, might just know more about the economy than you do.”
Brewster laughed. Not a chuckle. Not a snort. A full, head-back, teeth-baring guffaw that made a pigeon three feet away question its life choices.
“Eddie,” he said between breaths, “you think you know more than me? I run a multi-billion-dollar financial empire. You shine shoes.”
“And yet,” Eddie said with a wink, “I still have more hair than you.”
The shoeshiner’s theory wasn’t entirely unfounded. Over the past six months, he’d made a series of off-hand predictions that made Brewster uncomfortable. In January, he said, “I got a gut feeling crypto’s gonna crash harder than my cousin Lenny on rollerblades.” Two weeks later, Bitcoin dropped like it saw a spider.
In February, Eddie offhandedly mentioned, “This new electric scooter company everyone’s raving about? Flash in the pan. Trust me, I know a scam when I see one—I once paid to watch Cats on Broadway twice.”
Three days later, the company filed for bankruptcy after their scooters caught fire in three major cities and a minor suburb in Ohio.
By March, Brewster was sweating. He started checking Eddie’s “gut feelings” against the bank’s official reports. More often than not, Eddie was right. Coincidence? Luck? Or was the universe trying to tell him he’d been taking financial advice from spreadsheets, when he should’ve been listening to the man with the shoe rag?
So, Brewster did the unthinkable.
He invited Eddie to lunch.
At a steakhouse, no less. The kind of place where the waiters wear tuxedos and ask you if you want your water “with lemon, or with existential crisis?”
They sat at a private table, under a chandelier shaped like a cow’s revenge.
“I want to hire you,” Brewster said bluntly, slicing into a filet mignon that cost more than Eddie’s monthly rent.
Eddie dropped his fork. “To do what? Shine shoes in your boardroom?”
“To advise me,” Brewster replied. “You’ve got instincts. And for reasons that defy logic and finance, you’ve been right. Consistently.”
Eddie leaned back, chewing on a breadstick like it owed him money. “So, let me get this straight. You’re offering me a job, in your bank, because I said the scooter company was doomed and I think oat milk is a pyramid scheme?”
“That’s… the general idea, yes.”
Eddie grinned. “Do I get dental?”
One week later, Eddie became the most unconventional financial advisor in Manhattan. He swapped his shine chair for a corner office with a view of Central Park and a mini fridge stocked with Yoo-hoo and pickles. He still wore his bowtie. He still polished shoes—his own, mostly, out of nostalgia—but now he did it while giving investment advice that baffled the board.
“Buy stock in this random cereal brand,” he said during a meeting. “My cousin just got a job there, and every time he touches something, it turns into a viral TikTok trend.”
The boardroom laughed. Until three months later, the cereal company launched a “glow-in-the-dark marshmallow campaign” that made them the hottest brand on social media.
Eddie said, “Don’t trust that tech startup. Their CEO blinks too much. That’s liar energy.”
They ignored him. The startup was later revealed to be faking AI-generated financial reports with quotes from SpongeBob.
Meanwhile, Brewster’s bank was thriving. Investors loved Eddie. He became a legend—half oracle, half street philosopher, and somehow always smelling faintly of shoe polish and cinnamon gum.
One morning, Brewster found himself sitting in Eddie’s old shoeshine chair, just for fun. Eddie, now in suspenders and holding a gold pen, looked down at his former client.
“Funny how things change, huh?”
Brewster smiled. “Yeah. I miss the old days.”
“You mean when you thought you were smarter than me?”
“I still have an MBA, Eddie.”
“And I still know which bathroom stalls have the best Wi-Fi in this building. So who’s really winning?”
Then Eddie paused, glanced at the Wall Street Journal Brewster had brought, and said, “Sell everything related to penguins. I had a dream.”
And just like that, the Antarctic Investment Fund lost 12% in two days due to a documentary that revealed penguins are, in fact, terrible roommates.
Eddie became a legend. Brewster retired early, moved to Vermont, and opened a bookstore with no business model and a dog named Satoshi.
But every morning, he still reads the Wall Street Journal.
And wonders what Eddie’s gut is saying today.
