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.