If A Wealthy-Looking Man Dropped Some Money, What Would You Do?


Last week, my wife Fatima faced an interesting conundrum in the subway. She walked down the stairs and was greeted by a homeless veteran in his late 60s or early 70s. She didn’t have a dime on her, so like many of us do, she smiled, apologized, and continued to the platform. A few minutes later, a very well-dressed white man (we’re talking tailored Hugo Boss suit, Gucci shoes, Movado watch, the works), walked by shuffling through his bag (a leather attaché case), and dropped a crisp $20 dollar bill. He continued to walk, not turning back.

Fatima made a decision. But before telling anyone, she decided to ask her social media circles what he or she would do with this post:

“White man in a suit and fancy shoes drops a $20 on the subway platform. I made a decision, but what would you do? Give back to him? Or to the homeless vet by the stairs?”

The responses were fascinating. Out of 30 comments, 28 emphatically stated that the right thing to do is to return the money to its rightful owner. Two people said they would give the money to the homeless man. The 28 who preached morality made their own assumptions about the well-dressed man to support their decision.

“The suit/shoes could be borrowed.”

“Give it back, it’s not yours to give away.”

“Maybe he’s on his way to an interview, who knows?”

“If he were that fancy, he probably wouldn’t be riding the subway.”

That evening we had friends over for dinner and posed the question to them and an interesting discussion ensued, not at all about what they might do with the $20, but instead about the types of assumptions we make about different types of people.

It was intriguing that so many people quickly began to give the well-dressed white man, who had a $20 in an attaché case in the first place, the benefit of the doubt.

But so often, when a homeless person asks for money, we make assumptions in our heads about what they will do with that money – buy drugs? Alcohol? Cigarettes? We think about giving them food or water or the number to a shelter instead of the money they are asking for.

We wonder why they are homeless to begin with. We debate what kind of homeless person is more or less deserving of our money.

Would anyone ever stop and think that the well-dressed white man was off to buy drugs with that $20? In some ways, that is more likely.

Would anyone assume that perhaps he was a hedge fund manager evading taxes year after year contributing to the cutting of benefits for veterans? Would anyone think that perhaps he stole that money from someone else?

What about homeless people? What if they are asking for money (as opposed to food) because they are saving up for new clothes or to try and get in a hostel? When offering apples or sandwiches, does anyone ever think that maybe this person doesn’t like apples or sandwiches? Beggars can’t be choosers, right?

Society loathes poor people. They are bad, lazy, dirty, and immoral. But people with money – well they deserve it. They work hard, why else would they have it?

Here’s what one of the two people who said they would give the money to the homeless man said:

“Give it to the homeless man! The one who doesn’t have privilege like the white man in the suit, who is in dire need of every basic requirement for human survival, who society has failed by allowing human beings to be homeless, hungry, neglected, and left to rot.”

And here’s what Fatima did:

“I gave that money to the homeless man and didn’t think twice about it. In that moment, the $20 doesn’t belong to the man in the suit or to me. It belongs to the person who needs it most. I doubt a finely tailored Hugo Boss suit is borrowed and no smart person, fancy or not, takes a cab from midtown Manhattan during rush hour.”