The Shoeshine Boy’s Street Story

Listen to this story narrated by master storyteller Otis Jiry

“Shine? I’ll make ya shoes look fine!

The man passed 10-year old Leroy like he wasn’t even there. It was getting dark and soon there would be no chance of making any money. Reluctantly, Leroy folded up his little stand and seat.

He had a long way to walk back to Harlem. He couldn’t afford any kind of transportation. Not even the subway. Every penny he made went to keep his family from starving. His father was dead. His mother who had a terrible case of gout, could barely move on some days.

His three sisters, all older than him, did what they could to help provide funds for a roof over their head, and food. Being black, and poor, almost guaranteed they would never leave the slums of Harlem.

Because of bullies, and territorial gangsters, Leroy was forced to always keep moving where he did business. Some days he walked miles, relocating three or four times out of necessity’s sake.

Leroy learned his way around over the course of several years. He got to know which neighborhoods to avoid, and where it was safe to set up shop. Still, there was always new neighborhoods to explore in his search for money.

It was a new neighborhood where he hit his best payday ever!

All day long, men in dark clothes passed the Funeral Home near where he set up his stand. Many of them wanted a shoeshine. All were quiet and extremely generous, leaving him tips.

He lost track of time until the last shine, when darkness crept up on him like a thief. There were only a couple of street lamps working. Most were dark. Leroy pulled his threadbare coat around his chest tighter and shivered. A cold wind struck up as he starting walking down the street.

He was looking over his shoulder and didn’t see the man until he bumped into him! He immediately dropped his stand and covered up his head, fully expecting to be hit for his impropriety.

When nothing happened, he looked up and saw a tall pale man smiling at him.

“Sorry sir, I….”

“Don’t worry about it boy. We all get in a hurry sometimes, and make mistakes. Could I talk you into shining my shoes right now?

Despite Leroy’s misgivings about the strange-looking man wearing an 18th century coat, he set up his stand under one light that worked.

Fear tiptoed through his head as he dutifully buffed the man’s antique shoes. He knew shoes. He was sure he never saw anything like these ones.

When he was done, Leroy shyly asked if the stranger approved of his job?

The man stroked one end of his long black mustache and nodded agreeably. “Yes, well done boy. Here’s your reward.” He handed Leroy a gold coin. His eyes widened in surprise. The only gold coin he’d ever seen was in a pawn shop.

“Thank you,” he stammered.

“I’ll make a deal with you. Meet me once a month on this same day after dark, and I will continue to pay you with a gold coin. You must never tell anyone about our arrangement however.”

“Yes…” he assured him, “I won’t tell anyone.”

Then the stranger was gone.

After he got home that night he showed his sisters his prize. They were dumbfounded and excited. The next day all four kids went to the pawn shop where their uncle worked. The uncle’s eyes opened wide in surprise after examining the coin.

It was a $4 gold piece called a “Flowering Hair Stella” and was worth hundreds of thousands of dollars! The uncle was trembling when he picked up the phone and called an appraiser he knew.

“I’d guess you’ll get somewhere around $200,000 at auction,” the expert said.

All four kids screamed out loud in joy! The uncle was busy figuring out how he could get a cut of this sudden good fortune.

A month later life had changed drastically after they moved into a new house in a nice neighborhood. This sudden life of luxury caused them all to go a bit crazy and they spent most of their money.

Leroy thought about what the stranger said. He unpacked his old clothes which he couldn’t bear to throw away, and put them on. It took him a while to find his shoeshine stand. Someone had put it in attic.

He showed up at the same street where he met the stranger just before dark. The poor lighting caused shadows to undulate along the buildings and pour out into the street. He was looking at the ones across the street when he heard a cough nearby.

“Ahhhhum,” the stranger said, “You’ve returned to shine my shoes, I see.”

“Yes sir,” Leroy meekly agreed.

This time the stranger was more talkative.

“What did you do with the gold coin I gave you” he asked.

“I used it to put a roof over my family’s head, and for food for all of us,” he answered.

“Excellent! Good boy! Here’s your payment for tonight’s work.”

He handed Leroy a gold coin that looked just like the other one.

“In a month then?”

Yes…thank you!

When Leroy returned home that night he showed his sisters the gold coin. Their excitement soon changed to suspicion.

“Where you gettin these coins?” Latasha, his oldest sister asked.

“Told you. I got it for giving a man a shoeshine,” he said sullenly.

The same man?” she queried.

“Maybe...”

“What you mean maybe? C’mon lil man, this is me! Your sissy.”

Leroy began to feel guilty. He loved all of his sisters and he was keeping a big secret from them.

“Yeah…it was from the same man.”

“How did you find him again?” Tisha, his other sister asked.

“Well, that’s easy,” Tonya, the third sister claimed. “He went back to the same neighborhood. Isn’t that right Leroy?

“Yeah.”

The next day all four kids, and their mother, went to an independent coin appraiser to cut the uncle out of this windfall. He proved to be an ass the last time, demanding finders fees.

The coin was put up for auction a month later, and sold for $250,000.

This time, the mother and sisters paid off their accumulated bills, and took the rest and invested it in the stock market. Two days later the stock market crashed on Tuesday, October 24th, 1929!

The following night Leroy kept his appointment with the stranger. Once again the stranger was talkative.

“So, what did you do with the last gold coin I gave you?” 

Leroy hesitated. He hated telling the truth and risking rebuke, but he was an honest kid.

“My family lost it,” he admitted.

The stranger’s eyes darkened in anger. He looked Leroy in the eyes as if reading his mind. His countenance softening when he spoke, “I’m sorry to hear that. Here’s your coin. It’s the last one you’ll get from me. Better luck with this one boy.

Leroy looked down in his hand and saw the same type of coin as the other two. When he looked up the stranger was gone. He stood there for minutes on the sidewalk, watching the fog creep in.

When he got home he hid the coin. He would wait until he was 21 years-old and could lay claim to it without any legal challenges from his family.

As Leroy neared his legal age, he was still shining shoes. He seemed to enjoy the streets however, and started telling fantastic stories that his customers enjoyed. Their favorite story was how Leroy was really rich and was doing this – shining shoes – to pass time.

As It Stands, this was my twist on the generous stranger genre.

Dreams for Sale

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The piece of paper on the bulletin board in Woolworth’s said, “Dreams For Sale – 212-2641-0977.”

Alfred Oates blinked through his thick glasses and took his new Reynolds Rocket ballpoint pen out of his jacket pocket.

He carefully wrote the phone number down in a little notepad he kept in his other jacket pocket.

The year was 1947, and America was bursting with opportunities for clever men and women. Good jobs were available all over the country. Everyone was making money, one way, or the other.

Alfred made a lot of money, but had a peculiar problem. He couldn’t dream. He abruptly stopped dreaming when he became a teenager. Since then, he read everything he could find about his problem. There was precious little on the subject.

He wasn’t sure why he bothered writing the phone number down. It was probably some con man. But he had to admit, it was a clever way to get someone’s attention. He lit a Cuban cigar and leisurely strolled down the street until he came to the brownstone he was living in.

A black doorman in a tuxedo greeted him with a smile and opened the door. He walked into the luxurious lobby and headed straight for the front desk to get his mail. There were two letters. He took them with him, and went up the elevator to his room.

When he got to his room he put his ear on the door for a moment then inserted the key. He could never be too cautious in his line of work. The elegantly appointed room had a small desk and chair near the large picture window.

The first letter was from his brother who stayed in the Army after the war and was stationed in Germany. The second letter was business.

He memorized a street address in Manhattan, and carried a small black-and-white photo of a well-dressed young man in his shirt pocket. His hat was tilted slightly forward in the photo and made him look dashing.

Alfred went to his hotel’s parking lot and got the keys to his brand new 1947 Blue Hudson from the attendant. There was always someone on duty 24-hours a day to watch over the expensive cars.

It took nearly a pack of cigarettes and six hours before the man in the photo showed up. As the man approached the front door of his hotel Alfred got out of his car, screwed the silencer on his pistol, pulled up a handkerchief to cover the lower part of his face, and walked up to him as the doorman was greeting him.

Two quick shots to the head instantly killed the man. The doorman was spared. He shrieked with horror, as Alfred calmly walked away. Contract filled. He walked for a few blocks then turned around and took a different route to his car.

When he got back to his place he used the phone in the lobby to call the mysterious phone number.

Hello,” the deep baritone voice said.

“Hi. I’m interested in buying dreams. I saw your ad.”

“My room is located in Harlem. It’s in the Historic Harlem Duplex down the street from Columbia University. When would you like an appointment?”

“Yeah…sure.”

“Are you busy tomorrow?”

“I could work a time out,” Alfred said.

“Go to Room 13, at 1:00 o’clock.”

Alfred got a dial tone before he could agree with the time. As he left the ornate phone booth he felt silly. How could he logically think someone could sell dreams? If nothing else he’d whack the quack for trying to fool him.

The door opened after the third knock. A tall skeletal looking black man in a three-piece suit greeted him, “Good Day, Mr. Oates! Please come in.”

“Odd,” Alfred thought when he looked around the room. There was only a large desk and two heavily padded chairs. One behind the desk, and the other in front of it. Where was the bed he wondered?

“Please…have a seat,” the tall man urged him. Alfred sunk into the padded chair while studying the man as he went over to the other chair.

My name is Moses Gardener. I sell dreams. Been doing it for a long time. You are probably thinking I’m a fake trying to take advantage of you. Don’t worry, I deliver the goods.”

Moses opened a drawer and took out a small bottle made out of purple glass. He sat it down on the desk between them. Alfred’s eyes were riveted to the little flashes of light it emitted.

Carefully, Moses pulled the stopper out and tilted the bottle until a single round yellow pill came out. He laid it down in front of Alfred and closed the bottle.

“Because you’re a new customer, I’ll only charge you half of what I normally charge; one hundred dollars.”

“What guarantee do I have this pill will work? Your asking for a lot of money.”

“You know where to find me Mr. Oates. Take it, or leave it.”

Alfred paid him.

“Make sure to take it when your tired and ready to go to sleep. This is not a sleeping pill,” Moses advised.

Alfred sat on the edge of his bed and looked at the pill. Once again he wondered if this was worth it? What if the pill was poison? Then Moses wouldn’t have to worry about getting a visit from him.

Suddenly he didn’t care. He had no family. No friends. He really wanted to dream again. Closing his eyes he popped the pill into his mouth and chased it down with a shot of expensive bourbon.

When the dreams came they were convoluted. Faces flashed by. He was a boy again playing baseball in a dirty sand lot. Swimming in a pool. Playing stick ball in the streets. Falling in love with his 5th grade teacher.

The next morning Alfred woke up with a sense of sadness. He wanted the dream to continue. After getting dressed for the day and eating breakfast he called Moses.

“That’ll be two hundred dollars,” Moses said as he pulled the purple bottle out of the desk drawer.

“How do you do it? Where do you get these pills? I sure wouldn’t mind in investing in them,” Alfred said, as he peeled two one-hundred dollar bills out of his wallet.

“It’s a family recipe,” Moses answered.

Alfred hurried back to his place, eager for the night to fall. This time he didn’t hesitate to pop the pill.

His dream started out with his first kill. The owner of a restaurant who owed money to the mob. He saw the man’s shocked look as he shot him. But instead of falling down, the man grinned at him. His sharp white teeth gleamed with an unnatural light!

Then a crying woman appeared. Pleading for her life as he leveled his gun at her. Children were crying for their murdered parents. Blood ran down the walls in his bedroom.

He couldn’t wake up. He knew he was asleep. That knowledge terrified him. Two men suddenly attacked him with billy clubs! He felt the blows and the pain shocked him. Then he was stumbling around in a graveyard, and saw a headstone with his name on it.

When he mercifully woke up the next morning he was trembling, sweaty, and angry. Moses didn’t say anything about nightmares. He wanted his money back.

But Moses wasn’t there. The hotel staff said there was no room number 13. It was an unlucky number. Didn’t he know that?

That night, to his utter horror, the dreams came back and most of them were bad.

As It Stands, there’s a fine line between dreams and nightmares.

Why Bo Was A Lucky Man

A Harlem Legend

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“Riders on the storm, riders on the storm
Into this house we’re born, into this world we’re thrown
Like a dog without a bone, an actor out on loan
Riders on the storm…”

The Doors

Some people are just born lucky. Others get lucky for various reasons. 

Lucky people are sometimes called survivors. Bo was the luckiest kid born in East Harlem. All the residents pointed him out to strangers and friends, telling them how lucky he was.

“He had white horses
And ladies by the score
All dressed in satin
And waiting by the door
Ooh, what a lucky man he was…”

He Was A Lucky Man by Emerson, Lake and Palmer

Car went right over him the other day,” one woman said to another, as he walked by with his funny gait, and a twinkle in his eye.

“He was just lying there in the middle of 4th street and a car drove right over him, but didn’t even mess up his suit,” the woman told her friend. Her friend noted she saw a stuntman do that, and only someone looking for trouble would lay in the road in the first place.

“Maybe you don’t understand,” the first woman said. That Bo has been shot seven times and you just watched him walk by like the lord of Harlem.

Bo could hear them as he walked down the street. He smiled for a moment, then let out a heavy sigh. He recalled when his luck first started. Six years old. Everything was so wonderful back then.

His mom, on a whim one day, asked him to pick some numbers for the next lottery drawing. He did. She used them, and the next day she won $250,000! She couldn’t stop smothering him with her joy.

It made him feel a lot better about the deal he made the night before with his new friend Lievd.

But lucky as Bo was, he still ran into a lot of trouble. He did dumb things like jump from a second story window during a party, because he thought he could fly while high on LSD.

He survived. He wasn’t surprised.

For twenty-one years Bo had the art of being lucky down. He was banned from the game rooms in Harlem. His reputation as being lucky had it’s setbacks. Having to stay in Harlem was one of them.

It was in his deal with Lievd. As the years slid by, he forgot about how he got so lucky. But not everyone envied Bo. Those that knew him felt sad about his phobia…that he couldn’t leave Harlem.

His entire life was spent roving the streets looking for adventure. The decades slid by and Bo outlived his family and friends in Harlem. But he was still mentally sharp and went to the senior center twice a week to play chess.

One day he was playing a letter scamble game with the center director where the object was to make a word out of the letters given.

The letters were; evlid.

Bo tried to sort out what the letters said, re-arranging them in numerous combinations until he came up with a word that stopped him short: devil. He thought about Lievd and his deal.

It was only then that Bo realized he’d made a bad deal. He didn’t know what a soul was at six! At that moment he heard someone chuckle behind him. The Devil said, “Time to collect, with a wicked smile.

As It Stands, there’s been many variations of the devil making deals with helpless humans. This was my take on the genre.