As a libertarian (small “l”), I’m not supposed to be concerned with the homeless. On a purely socio-economic level, homelessness is the free market’s way of punishing those who don’t or can’t contribute to society. Yet, I am still looking for the elusive libertarian who is willing to let the physically, mentally, and/or psychologically handicapped starve on the streets. At the same time, it is highly debatable how much the homeless are willing to do to end their own despair. How fitting that I bring this up the night after #1 draft choice - turned tattooed alcoholic drug-addict - turned baseball all-star Josh Hamilton set the record for most home runs in a single round of Home Run Derby in one of the most remarkable tales of redemption:

I recently viewed John Stossel’s clip on homelessness. To be fair, Stossel is very free-market and presented a relatively one-sided view. He offers a cynical look at the homeless. The video suggests that the homeless milk the system, and our sympathy, becoming dependent. When offered a chance to rise above their situation with honest labor, they pass. They voluntarily choose their low standard-of-living in order to not have to work.

As if Stossel’s experiment of 12 homeless people (where only 1 actually shows up to mow a lawn for $6/hour) wasn’t anecdotal enough, I have my own vignette to share. This morning I stopped off at the 7-11 right by the El stop. I go in and grab my delicious $.99 23 oz. Arizona Iced Tea. While on line to pay for my Nectar of the Gods, I am behind a woman who is clearly homeless. Her clothes are ragged, her skin is worn, and most of her teeth are missing. I felt extremely awkward in my slacks, shined shoes, and button-down shirt. I was off to intern at a prestigious (you hear that, Sam Adams?) political outreach firm to pass the summer in between my education at a prestigious (you hear that, Northwestern?) university. She was off to panhandle and find her next meal. So the woman gathers her loose change and crumpled dollar bills. I tried not to see what she was purchasing out of respect. However, I couldn’t help but let my jaw drop slightly as she bought four $1 scratch-off lottery tickets.

I won’t completely speculate, but my hunch is this: a woman who is malnourished and lacking in the basics of an American lifestyle chose to spend “her” money on lottery tickets. I use the quotation marks around her because she was undoubtedly given that money by those who wanted to make sure she got a hot meal that day. That money was a gift, implicitly intended for necessities. If she told passerbys that she wanted to see if she could hit it big, then I doubt she would have the money to be buying up Mega Millions cards.

So what does this mean?

I think our society and government needs a more objective evaluation of the homeless situation. Why are they homeless? Are they being fed, clothed, and housed? I WANT to believe that the homeless need my help, and my spare change. More importantly, I NEED to believe that any money I give is going to serve a greater good. I don’t want to live in a society where I can rationally look down and psychologically spit on the poor men and women who go through the degrading process of asking random strangers for money so they can survive another day.

Instead of liberal groups which will believe the most far-fetched tales, let’s find some facts. It may be politically-correct and emotionally fulfilling to serve the needy, but it might not be necessary. Enabling a free-rider problem could be seen as having massive psychological and economic damages on the rest of the economy. All of the time and money that goes into charity work and government programs might be doing little more than empowering the lazy. Maybe.

I won’t wholly condemn the homeless community as a bunch of lazy, stupid, ne’er-do-wells because of one morning in a Chicago 7-11 and a John Stossel documentary. But, I certainly have to wonder about giving money to the homeless. If there are ample soup kitchens and shelters, where is my money going? If the basics are being covered by the government and private charity, what role am I playing as individual donor? Am I an enabler of drug addiction and abuse? Am I purely a symbol of human compassion? Am I simply a nameless face who gave a woman some dignity and let her make a luxury purchase? I don’t have the answers, but the questions are telling. I don’t know what I “believe” because I think each homeless person has his/her own unique story that represents a unique blend of bad circumstances and bad personal decisions.

Hopefully this sparks a discussion and gets people thinking. I assure you that those who offer carte blanche to the homeless and those who rank them just above dirt on the social hierarchy both could benefit from some good old-fashioned, political discourse.

Unrelated note: for those of you who know me personally (hi, mom and dad!), you surely must know that today is a sacred holiday for me. It marks the release of NCAA Football 2009, the newest installment of the greatest video game series ever. I think this year will mark the 9th straight year that I have purchased it. Surely even the most uninspired must worship at the altar:

Edit: changed to cover up for my stupidity and apparent lack of school spirit