Lessons From the Shoeless and the Homeless

by Stephen Mills on December 3, 2012

A couple of weeks ago a NYC policeman saw a homeless man sitting on a sidewalk in Time’s Square in freezing weather without socks and shoes.  He went into a shoe store nearby and bought the man a pair of fairly expensive boots with his own money.  Some tourist recorded it and the video went viral and made the national news. The woman who recorded the whole thing teared up as she described it to the national media.  The whole nation seemed to be touched by this act of kindness.

At the time I thought to myself I would have never done that.  Yes, I’m very cynical and I admit it.  While I love the idea of random acts of kindness, I believe they should not be mindless.  There has to be some criteria and that criteria needs to be more than if something is lacking it should be provided.  That’s what the government does and it creates all kinds of unintended consequences.  Some things may be a no brainer – an elderly woman struggling with a heavy package of some kind is a stereotypical example that comes to mind.  But when it comes to a man sitting on the street without shoes, the situation is a little more complicated.

I think the intent of the policeman was nothing but pure and that seems to be what touched everyone, however that does not mean it was the right thing to do.  I would argue that the failure to think about who you are helping and why is self-defeating.  That is unless you just want to feel good about yourself regardless of the consequences.  When I first saw the story I thought to myself that there has to be a reason he doesn’t have shoes in the first place and I would argue virtually anyone in the U.S. could have a pair of shoes and socks.  Therefore I’m not sure it is a good idea to give them to someone sitting on a sidewalk.  If you give them some cheap old used pair that might be a different story, but to go into a store and buy a new pair seems to be going across the line.  A cynic like me would think they will probably just sell them and buy wine.  Would you have bought him a bottle of wine?  If not and that’s what he does with the shoes you have effectively done the same thing.  On what basis do you have the information to make that judgment?  I don’t know what would happen one way or the other, but don’t kid yourself about what people laying on sidewalks are likely to do with any money you give them.  I’m not trying to be a scrooge at Christmas so bear with me a little.

I heard this morning the same man was found out on the cold streets again without his precious shoes.  Reportedly he said “those boots are worth a lot of money.”  Supposedly he is afraid someone is going to harm him in order to steal them.  Right.  I suspect he intends to profit from them, but even if you take him at his word the point is that despite the policeman’s personal gift and sacrifice, the shoes aren’t warming his feet.  The resources spent on providing them to him could have been put to better use.  If you believe the homeless man, they are stashed away and thus totally useless.  I’m extremely disturbed by something else he said.  Apparently he’s upset that the video went around the world and he is not getting “a piece of the pie.”  Regardless, the act of kindness did NOT accomplish its intended purpose, unless the purpose was for us all to feel good about a lovely story.  Give the money to a soup kitchen and let them feed a bunch of people for the same cost as the now useless boots.  You might give all your old shoes to the Salvation Army and buy yourself some new ones.

Everybody was able to get off on the beautiful story but for all we know it just fed a sickness like alcoholism.  A friend of mine time told me one time he had just left the dentist’s office with a bag containing the usual floss, toothbrush, etc.  He said while waiting at a corner he put a $5 bill in the bag and handed it to an apparently homeless man.  The man looked in the bag, evidently missing the $5 bill, then tossed it back at my friend with a disgusted look on his face.  I had a man tell me the same sob story about “just being released from the hospital” twice several months apart in the same B&N parking lot.  The second time, knowing for certain the story was a complete load of crap, I watched as the man hit up a couple of other guys.  As I entered the book store, one of them pulled out his wallet and handed the man some money.

People standing on corners panhandling or sitting on cold streets without shoes are probably not just people “down on their luck”.  It’s possible but not likely.  The vast majority of them have serious issues that are not going to be helped by thoughtless acts of kindness.  You can actually hurt people by trying to help them in ways that are not really helpful.  Most parents eventually learn this lesson even with their not-so-helpless children.  Bailing them out may actually hurt them in the long run.

I would rather give $5 to an organization that actually has some qualifications and experience in how to help people.  Organizations that give them something like a hot meal or a place to stay.  Your $5 bill handed to someone begging for it may not go to food, it may go to alcohol, drugs, a quickie in the alley, or something else not likely to to be recorded by a tourist’s camera and warm the hearts of the nation.  Driving by a corner or seeing someone sitting on the sidewalk, we’re in no position to make the kind of judgments necessary to do the right thing.  If you feel the need to help, think about it first.  Maybe you would be better off donating to an agency in a better position than you to decide what and for whom something needs to be done.


Get Free Updates to The Rat Race Trap by Email here or via a reader in the top left sidebar.  I would love to have you on board.

If you liked this article and think it might be useful to others please share by clicking the share buttons below:

{ 5 comments… read them below or add one }

Julie W. December 5, 2012 at 7:18 am

If I feel compelled to give a gift of charity, compassion, or affection, I think it is good for me to do so. If I believe I can control the recipient’s use of that gift, I am deluded. Once the gift is given, control of it is pretty much forfeit. This is true whether the gift is given to an individual or an organization. The individual may use my gift to feed his addictions, throw it away, or use it as it was intended. His choice, not mine. The organization may use my gift for the CEO’s salary, for some program I didn’t necessarily wish to support, or even for exactly what they led me to believe it was for. Their choice, not mine. “You pays your money and you takes your chances.” I believe it is better (for me) to practice charity out of compassion rather than the illusion of control. Compassion has never hurt me, but trying to control the behavior of others most certainly has. And, I prefer to love the living more than I love my money.


Stephen Mills December 5, 2012 at 8:29 am

Julie, you completely missed the point. As I said in the article if it is all about you and how you feel then go for it. Blind compassion is not necessarily compassion again unless it is all about YOU.

If you want to throw your money at people regardless of the consequences then go right ahead.

Finally, your implication that I’m suggesting control of others could not be further from the truth. Please explain how I’m trying to control the homeless man in the example. Not at all. He is perfectly free to do whatever he wants with the boots. That’s my whole point. That’s why you should THINK about the consequences of what you are doing and not just blindly throw stuff at people and let them do with it what they will. It is exactly because you can’t control what happens that you should carefully consider what you are doing.

Your giving seems to be all about YOU, regardless of the consequences. EXACTLY my point.


Ryan December 10, 2012 at 12:52 am

Maybe the homeless man meant “piece of the pie” as attention. The police officer got all of the accolades and attention. No one cared about the homeless man.


Brian December 10, 2012 at 2:35 pm

An interesting perspective on a difficult question Stephen. It is a challenge that we are faced with almost daily as city-dwellers. However, I have to add, that social conservatism on the part of the government will only make this problem worse.


Derrick December 20, 2012 at 7:01 pm

Great Article! For those who want to do the right thing. It can be contraversial to say the least. My practice when someone approaches me for money to help them out. First of all they must empty their pockets in front of me. No drugs or pipes etc. and 20 dollars or less. I pay for a nutritious meal and the company of myself to talk to during that meal. I have experienced at times fabulous results that leave a person feeling good. I have also been told where to go when I ask them to empty their pockets. 🙂


Leave a Comment

CommentLuv badge