Is the Guy with the Sign Worthy of Charity—Or a Con Artist?

A man wearing shabby clothing, standing on an urban street corner, holding a cardboard sign.

The Guy with the Sign and Other Thoughts on Faith in Everyday Life by Terry Pluto

Book Excerpt

From The Guy with the Sign, by Terry Pluto

I received this email from Robin (not her real name):

“After church, a young man was standing right outside the door saying that he was homeless and hungry. I passed by him as I was speaking to another parishioner.

“I felt bad, walked to my car where I keep money in the glove compartment. There was only a $10 bill. I sat there deciding whether or not to give it to him, as he might be using it for drugs. I decided not to, and drove away the whole time feeling bad. Had there been a $5 bill or singles, I probably would have given it to him.

“I still feel bad and am reflecting on my decision. Why did I put a value on what he deserved? Why did I want to determine how he would use it? I give to organized charities monthly, why couldn’t I give when it was up close and personal?

“I would never have missed that $10 and feeling foolish would be much better than the reproach I now feel toward myself.”

Robin asked me for guidance.

I called the Rev. Jeff Kaiser, CEO of the Haven of Rest Rescue Mission in Akron, and read Robin’s letter to him. He quickly said Robin was wise to donate monthly “to organized charities.” He said a good way to help the homeless was to give to organizations that work in the field. I’ve also done a few fundraisers for the City Mission of Cleveland over the years. It also does great work.

There are lots of good organizations, including the Salvation Army, Catholic Charities and local places of worship that have outreaches to the homeless. I’m sure there are many others. A little research will lead you in the right direction.

“If you want to be sure your money is used well, charities are a good place to start,” said Kaiser. “We can point people in need to different agencies and places that will help them if we can’t do it.”


But what about the guy on the corner with a sign?

“A guy like that changed my life in some ways,” said Father Bob Stec, pastor of St. Ambrose Catholic Parish in Brunswick.

Stec said a man approached him on a downtown street holding a sign and asking for money.

“Can you help?” asked the man. “I’m Jesus Christ.”

Stec stared at him for a moment.

“How do you know I’m not Jesus?” asked the man.

It was an interesting question. The man could have been suffering from an emotional issue, really believing he was Jesus. Or he could have been saying that when you see the least among us, you see Jesus, as in Matthew 25.

Stec gave him $5.

“You really don’t know the person with the sign or how they got there,” said Stec, who carries extra $5 bills to give away.


If you give someone with a sign money, you have to understand it could be used for drugs or alcohol. Or maybe not. No way to know.

“We’ve had a 140% increase in overdoses in Akron since January (in 2020),” said Kaiser. “That really worries me. I know for a fact some of those are from people we see with signs, because of the work we do.”

Kaiser understands, “If the Lord moves you to give to someone, go ahead and give.”

But he also stressed the streets can be dangerous.

I’ve told My wife, Roberta, not to give money to people on the corner when she’s stopped at a light. I’m not having her take any chances, especially after she had an occasion where she gave a man a dollar—and he began pounding on the roof of her car, demanding more money.

Others can make their own decisions.


I’ve seen some guys with signs scream at each other to secure prime spots to ask for money.

I’ve seen some men with their signs for years. Same men, same corners. Some of them probably can work, but don’t want to deal with the restrictions of a job. Others are a different story due to physical and/or emotional limitations.

But I don’t know their personal situations.

I once saw a few get together to figure out where they planned to set up. It was a meeting. They each had signs and cellphones.

Someone from our jail ministry told me how those guys coordinated with their cellphones. They pooled their money at the end of day. One guy had a car. It was like their business.

Sometimes, you’ll be at a convenience store and someone will approach you with a gas can wanting money for fuel. “One of the oldest in the book,” as one man from the Haven of Rest told me. If you want to help, tell them to go inside the store with you and you’ll buy them something to eat.


I usually hand out dollar bills to some of the regulars. Some have emotional and physical problems and do need the help. Other times, I just give the money—and not worry about what happens next.

Not many women seem to be out with signs. I always give to them. I got to know one woman who was at a certain corner. She had a major back injury and other health problems. Not everyone is running a con game.

Sometimes, I will quickly pray for someone I encounter, and remind them, “This is God’s money.” Most seem to appreciate that.

There is a man holding his sign, smoking a cigarette and sitting on a bucket turned upside down at the same intersection for more than a year. He also limps and looks as if his face has been used for a punching bag. I usually give him a dollar each time I see him.

Sometimes, I’ve given out extra pairs of socks. Most people love getting those. I know of someone who hands out McDonald’s gift cards. It doesn’t have to be cash.

“At St. Ambrose, people come in each week and make sandwiches,” said Stec. “We have seven places where we deliver the sandwiches across the city. There are a lot of ways to help the homeless.”

I don’t have a good answer for Robin, other than working with charities is the safest and best option. To give or not give on the street, it’s a personal decision.


I once was walking into a Circle K store. A young man came up to me. He was totally hammered, reeking of alcohol and marijuana. He wanted money. He recognized me from my speaking at the Haven of Rest.

“Let’s go inside,” I said. “Get some food, I’ll pay.”

We did that. Then I prayed for him.

About a year later, I ran into the man, who was in the drug rehabilitation program at the Haven of Rest. He reminded me of the Circle K store story, which I’d forgotten. He said that night was the start of his decision to try to get sober.

“You never do know how God will use you,” said Stec. “That’s something I’ve learned over the years.”

Terry Pluto talk: Vintage Browns and Other Cleveland Sports Stories – Music Box Supper Club – Cleveland

Vintage Browns: A Warm Look Back at the Cleveland Browns of the 1970s, ’80s, ’90s and More, a book by Terry Pluto

Cleveland sports columnist Terry Pluto talks about the Kardiac Kids, the Dawgs, the old Stadium, Bernie and Marty and Ozzie and other Vintage Browns. Plus, he’ll talk current Browns and other Cleveland sports and take questions from the audience.

Event is FREE and open to the public. Part of the Cleveland Stories Dinner Parties series. Dinner is available (optional). Reservations are available. Doors open at 5 p.m. Talk starts at 7 p.m.

Please note: Proof of Covid-19 vaccination (card or photo is acceptable), or negative test (time-stamped, no older than 72 hours) is required to enter. Masks are suggested except while eating and drinking.

More info and reservations at Music Box Supper Club website.