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Should We Give a Homeless Man Shoes?

12/05/2012 01:46 pm ET | Updated Feb 04, 2013

It started out as the most heartwarming story of the week. A NYPD cop caught in the act of buying socks and shoes for a homeless man he saw barefoot on a cold night.

"I had to help" Officer Larry DePrimo told CNN, "You could see the blisters (on his feet) from 15 feet away."

The photo of DePrimo helping the man taken by a tourist went viral with more than 400,000 likes and made many feel good about the possibility of individuals doing good. As DePrimo said on The Today Show: "People are saying their faith in humanity is restored and that's the biggest thing I can take away from all of this."

But the story didn't end there. And the moral questions the story evoked got more complicated.

Just days after DePrimo bought the homeless man the shoes (said to be worth around $75), the New York Times reported that the man was out on the streets without shoes again, claiming he hid them because they were "worth a lot of money." What's more, the man wanted a perceived "piece of the pie" from the viral photo.

A few days later, it was reported by the Daily News that the man, whose name is Jeffrey Hillman, is not technically homeless but has an apartment in the Bronx secured through the Department of Veterans Affairs, and that he has turned down offers to help from both social service and family. What's more, the New York Post reported that Hillman has a history of run-ins with the law for drugs, harassment, theft and more.

So. What are we to make of the morality tale of giving the homeless man a pair of shoes when the man is not homeless, has an undesirable past and has apparently discarded the shoes?

When I first saw the photo and heard DePrimo's story I, like the rest of the world was challenged. "Why don't I do that?" I asked myself. "What stops me? I'm going to buy someone some shoes," I thought.

But as the news unfolded about the "homeless" man's actual situation, my head, along with the rest of the world, collectively tsked tsked and replied knowingly "That's why we don't buy shoes for the homeless."

OK. Back to our cynical starting place. Our collective faith in humanity is weak exactly because of this kind of story. And the moral is don't give to the homeless on the streets.

But is that the right moral lesson to learn?

Should Hillman's complicated, messy life and response to this act of generosity mean that DePrimo should not have given him the shoes on that cold night? Should I ignore the woman or man on the street asking for money?

Arnold Cohen, President of the Partnership for the Homeless in New York City says that is the wrong question to ask. "We should be asking why there are so many people on the streets," Cohen told me, "And why a rich city like ours is so ill equipped to deal with the complexity of homelessness -- because it is very complex."

Cohen says that the fact that he has an apartment doesn't change the fact that clearly Hillman, and people like him on the streets and subways are struggling. "People say 'this is a lifestyle choice' -- it's not."

When I asked Cohen if he thought Officer DePrimo did the right thing by buying the shoes for Hillman, his first response was to reference the great Jewish philosopher Maimonides who said: "We should be giving without judgment;" but he added that giving to individuals like Hillman will not solve the complexities of the problem of people on the streets.

I next talked to Christian ethicist David Gushee who recalled the disheartening experience during seminary in New York City when he gave a substantial amount of money to a man who was broke but was desperate to attend his father's funeral. He felt sucker punched when he saw the same man pitching the same story to another unsuspecting do-gooder a week later.

"There is something in the human spirit that wants to believe in and reward expressions of love and compassion for those who are in need," Gushee said about the story of the homeless man and the shoes.

"And Jesus said 'Give to those who ask'" reminded Gushee, but then he added that perhaps in the 21st century Jesus' mandate needs a footnote that the best way to give is by directing financial charity to those who know how to deliver it intelligently.

Princeton religion professor Eric Gregory had a slightly different take reminding me that in the last centuries there has arisen a distinction between the deserving and undeserving poor but the biblical witness doesn't seem to distinguish between the two. "The Good Samaritan didn't stop and ask the man on the side of the road 'how did this happen'" Gregory said, "He responded to an immediate need."

Gregory argues that the current conversation about "smart money," or money that is used for the most good loses the personal encounter with those who suffer and the challenge of the question: "Am I my brothers keeper?"

Professor Gregory said that while those who are receiving such direct aid might be complicated, selfish and difficult -- so are we. He reminded me of something the theologian and author C.S. Lewis wrote: "Another things that annoys me is when people say, "Why did you give that man money? He'll probably go and drink it." My reply is, "But if I kept it, I should have probably drunk it."

DePrimo's example is commendable -- perhaps more so because, as a cop, he knows that people on the street have messy lives.

Yes, we have a responsibility to ask the questions of why people are poor, to lobby for better treatment of the poor, to support agencies that who have expertise with the poor, but we also should also be inspired to give directly to the poor. Not because it is the most effective, but because the direct encounter with those who are suffering, and the courage to give without controlling how it is received is important for our own spiritual well being.

Hillman responded to DePrimo's offer to buy shoes by saying God bless you. When we overcome our city honed instinct of isolation and suspicion to do an act of kindness and show compassion to the stranger it is, in that moment, a blessing experienced by both the giver and receiver.

In this messy world, that is more than enough.

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