I started this blog for a few reasons. One, because I was bored at work and wanted to expand my diversions. Two, because Tony keeps me entertained and is an example for everyone, even if he dislikes futbol and thinks the US has no business playing it with the Euros. And three, because I see this homeless man every day, and every time I see him, I get really pensive and I finally need to just do something about it.

I think many of us have the same general reaction when we encounter the homeless on the street requesting our good will and our spare change. I always feel sympathetic, because in truth I really believe that most of these unfortunate people caught a run of bad luck and they just didn't have much of a way to rectify things. But at the same time, I am always very reluctant to part with a few of my hard earned quarters (those get saved for laundry day) or other change. Why? One might suppose that I have no way of knowing where my good will goes, be it for food, a holey jacket in February or a pack of Marlboros. I'm not sure. I do know that I have given money to organizations designed to help the homeless, and I have volunteered my time to a very excellent organization. Nonetheless, every time I do feel a little guilty for having a good job and all the opportunities that I have had.

But I will admit that after seeing the same people every day using the same tired pleas for money, I tend to get skeptical and instead find myself buying the newest copy of Streetwise from that guy outside of Starbucks on Madison who is so nice and makes a personal connection with everyone.

But I see this one man every morning, and I just cannot figure him out. And it's driving me nuts.

He's probably in his late 50s or early 60s, and he rides his bike to the southeast corner of Madison and Franklin every day and sets up shop. He always brings his very cute and well-behaved dog with him, which rides in one of those bike trailers you see yuppie parents toting their niƱos around in all the time. His bike is not the finest piece of equipment ever and neither is his doggy trailer, but they work and get him around pretty well.

He has a kind face, nearly always with a smile. He wears jeans and some sort of flannel shirt in the middle of July when it's a million degrees with 400% humidity and in the middle of February when I swear I am moving back to LA. Sometimes he plays the harmonica. Sometimes he does not. But he always just sits there with his hat on the street, never saying a word to anyone who does not approach him first.

In my two years of walking by him, I've never once not seen at least one person petting his doggy, sharing some words and dropping the man at least a buck, sometimes a fiver or more.

I cannot decide if he has the biggest scam running or if he is the perfect example of everything that is good in our collective spirit.

By my conservative estimations, he probably brings in $30-$40 on an average day, sometimes more. This works out to be $150-$200 a week, $600-$800 a month. Not a goldmine, but easily as much as I was making back in those days of working 10 hour shifts as a lifeguard. Certainly enough to take some sort of initial steps toward something if he wanted to, I would think. Anyway, it's quite possible that I am badly estimating things or something, but I'm only going off two years of personal observations, so draw your own conclusions.

Everytime I see him I have all these questions run through my head. Is he really just working these commuters left and right, knowing exactly what plays out well? Or is he just extraordinarily fortunate that we'll take care of him and his doggy? And why is he the one to which all we white collared opportunities abounding folk are funneling our generosity? Does he represent what we fear we might be, or does that face just inspire confidence? And where does he go on Saturday and Sunday?

I always find myself asking a lot of questions of myself at the same time. Why on some days do I assume he's scamming the good people of Chicago? Why do I assume that he's doing well enough that he could go find some more "respectable" source of income. What makes me think his way of doing things is even questionable? And maybe above all else, why have I never flowed this gentleman a dollar and stopped to learn his name, who he is, and why he's at the corner in jeans and a flannel shirt while my scarf is practically suffocating me just so I can keep warm. Why am I hesitant to find out?

I think maybe I'm afraid to find out because then I will stop thinking about it all and I won't have to ponder the deeper mysteries of all this behavior anymore. All because of one man and his dog. It's very strange.