Inspirational Stories

October 18, 2021

Owner Dresses up as Homeless Person and Visits His Restaurants to Determine His Heir – Story of the Day

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Mr. Carter Santiago had been contemplating his life and realized that he had yet to make a will. But who would inherit his estate, which included several luxury restaurants in Chicago? So he decided to conduct a test and discovered something unexpected.

Despite what most of the city of Chicago might want you to believe, Mr. Santiago did not come from old money. His mother raised him alone while working minimum wage, and he took odd gigs around his hometown of Aurora, Illinois, to help out.

Mr. Santiago started washing dishes at a restaurant, and he eventually became an assistant cook. But he wanted to do more. So he started taking night business classes at the local community college and later became his own boss.


Mr. Santiago came up with a plan to test who should get his estate. | Source: Shutterstock

His first restaurant was small and had a simple menu. But it was brilliant and popular with people. Then he asked for his first bank loan to open a place in Chicago, and his success took off from there. His restaurants won awards.


The best chefs from the country wanted to work for him, and it snowballed from there. He was the most respected restaurateur in the area. 

But as time passed, Mr. Santiago couldn’t manage to run his restaurants anymore because he could barely leave his house due to illness. His doctors explained that it might be time to get his affairs in order, and that’s how he ran into a dilemma.

Mr. Santiago didn’t have family left. He never found the love of his life despite receiving tons of female advances and he had no children too. Who should I leave my estate to? He often wondered.

Most of the managers turned him away. | Source: Pexels


One of his lawyers suggested leaving it to a mentee or charity. But he wanted to think things through before formalizing his will. He sat down on his wide front porch with a notepad.

“Whoever I leave this to needs to have struggled like me to appreciate it truly. How can I find out? Should I look at the managers' and chefs' resumes? That seems so impersonal,” Mr. Santiago mused out loud.

But inspiration hit, and he devised a plan. He dressed in his oldest attire and bought a shabby second-hand cane. He grew out his beard before heading out to visit his restaurants.

“Sir, I’m sorry. You can’t come in here,” the manager of The Mockingbird said. And when Mr. Santiago tried to insist, she called the security guards.  Ok, you’re not getting anything, he thought and headed towards his other restaurant called Lueuer des Étoiles.


“Go away, old man! Homeless people are not allowed in this Michelin-starred place. You can search the garbage after we close for leftovers,” the hostess sneered down his nose at him.

He reached Bambino, went to the back entrance, and the head chef greeted him. | Source: Pexels


Yikes, I don’t have the best employees in the world, he noted to himself as he walked away. But then again, Mr. Santiago had not been in charge of hiring in decades. He had a management firm that handled all that stuff.

Next, he showed up at Cinnamon, a popular bar-restaurant among Chicago’s celebrities. But once again, he wasn't allowed to go inside. “Man, get out of here. This place has a dress code, and it’s way too expensive. You can try the nearest soup kitchen,” another hostess snapped.

He was losing hope. I guess none of my employees think everyone deserves friendly treatment, he thought sadlyBut Mr. Santiago wanted to try out one more place, Bambino. This restaurant looked fancy, but it was similar to his first place in Aurora. It served delicious and authentic Italian food, which was his favorite.


This time, he decided to go to the back and test things out from there. He knocked on the back entrance, and the head chef came out. “Yes?” he questioned.

They treated him just like any other customer. | Source: Pexels


“Can I get a meal here? I have money to pay,” Mr. Santiago declared.

“Give me a second,” the chef answered and closed the door. Mr. Santiago was sure the chef was about to bring the manager and possibly a security guard to run him off. Fortunately, that didn’t happen. The chef opened the door and ushered him inside.

“Thank you. What is your name?” Mr. Santiago asked.

“My name is Benjamin Flynn. I’m the head chef here,” Benjamin replied. He led Mr. Santiago to a table near the kitchen. This was a private part of the restaurant and impossible to get. The older man thanked him as he sat down.


They treated him like royalty, and when Mr. Santiago asked for the check, the chef said he had already paid. “Why would you do something like that? I said I have the money,” Mr. Santiago said, pretending to be angry when, in fact, he was pleased.

Chef Flynn explained his past and why he had been so nice to the older man. | Source: Pexels


“Sir, I know you probably saved that money for a long while to eat here. The food is fantastic, but some of the prices are a little too high in my opinion. You should save that money,” Chef Flynn revealed.

“You know a lot of other restaurants didn’t let me in. Why did you?” Mr. Santiago asked.

“Ah, that’s terrible. I mean if you have the money you should be able to go anywhere. I let you in because I know what it’s like to be in your position. I was homeless for a long while until one kind man offered me a job years ago. He trained me to become a chef,” Chef Flynn explained.

“And now you’re here. I heard this is one of the best places in town,” Mr. Santiago added, wanting to know more.


“Yes, it is. It’s also the perfect job. I admire the restaurateur who created it. I plan to open my own place one day, one that will welcome anyone, rich or poor. But this is great for now," Chef Flynn stated.

Wendy told him the older man had left a thousand dollars on the table. | Source: Pexels


Mr. Santiago was surprised Chef Flynn didn't recognize him, but it must be because of his homeless disguise. “Thank you, young man. You gave me a great deal to think about,” he told the chef. Then, Mr. Santiago stood up, left several dollar bills on the table, and walked away.

Meanwhile, Chef Flynn waved the older man goodbye and continued working. “Chef, the man left $1,000 on the table,” one of his waitresses, Wendy, said.

“What? That’s impossible,” Chef Flynn frowned. After Wendy handed him the money, he went outside and tried to find the homeless man to no avail. He decided to divide the money among his staff.


A few months later, he heard about Mr. Carter Santiago’s passing and was surprised to see his picture on T.V. A week later, he got an even bigger shock when Mr. Santiago’s lawyer contacted him.

Mr. Santiago gave him everything including a short letter. | Source: Pexels


The older man left him everything, including a short handwritten letter, which explained his homeless man's disguise and why he chose Chef Flynn as his inheritor. 

The letter ended with: “I hope you’re up to the challenge of being the most important restaurateur in town. Your food is good, but now comes the hard part. Good luck!”

What can we learn from this story?

  • Everyone deserves respect. While most restaurants maintain their right to deny service, there’s no need to treat people like they are less-than.
  • Good things come to those who earn them. Mr. Santiago worked hard to become rich, and he saw that Chef Flynn had the same spirit, unlike some of his other employees.


Share this story with your friends. It might brighten their day and inspire them. 

If you enjoyed this story, you might like this one about a boy who spent the night in the attic playing hide-and-seek.

This account is inspired by our reader’s story and written by a professional writer. Any resemblance to actual names or locations is purely coincidental. All images are for illustration purposes only. Share your story with us; maybe it will change someone’s life. If you would like to share your story, please send it to