Businessman Pretends to Be Homeless So He Can Give Money Away

“I thought this was also a way to acknowledge those who give, who do so anonymously,” Wright said.

In his letter, Wright encouraged the people to use the money as they wished or to pay it forward.

“I was blown away,” said Rob Taylor, of West Des Moines, who opened his envelope later that day. “As a matter of fact, the first thing that I did was call my wife on the phone and I could hardly talk to her on the phone. I said, ‘You wouldn’t believe what just happened to me.'”

Taylor said he appreciated the gesture.

“For my family, it reminded everyone what the meaning of Christmas was and it wasn’t about gifts, it’s about giving back,” Taylor said.

This is a nice gesture and all—I am not homeless and I could surely use $100 and I’m sure the people who received the money are kind and good and maybe some of them did “pay it forward”—but I just can’t wrap my head around deliberately prioritizing under-appreciated generosity over actual homelessness and starvation.

Wright says he doubled the money he collected from do-gooders—an unspecified amount, but probably not much—and donated it to a local homeless shelter. In reciprocation for those donations, he says (the “giving back” part of the experiment), he handed out nearly $1000 to generous strangers. Then, presumably, he stopped being fake-homeless and went home to his house. I don’t mean to nitpick here, but just an idea I had for your grand gesture of charitable giving: TAKE ALL OF THE MONEY AND GIVE IT DIRECTLY TO ACTUAL REPUTABLE HOMELESS CHARITIES THAT HELP PEOPLE WHO ARE STARVING AND FREEZING TO DEATH.

I’m not faulting Wright’s generosity here (people are welcome to do whatever they want with their money, and any amount of giving is worthwhile), I’m just criticizing the lack of efficiency in his system of “giving.” When you’re dealing with an issue as massive and urgent as homelessness, you can’t afford to be inefficient. If you want to actually affect meaningful change to alleviate real social problems, this is not a helpful way to help. This just falls under the category of “a nice thing to do.”

I’m sure Wright, with his hoodie and his sign, probably didn’t read to passersby like one of those homeless people—the bad kind of homeless people, the kind with visible addictions and mental illnesses, the kind who are thought of as tainting our streets instead of suffering on them. Doing nice things for one another is nice. But mostly what I see here are a whole lot of non-homeless people feeling great and a whole lot of homeless people feeling cold.