On my way home, I did something that was very out of character for me. I gave $10 to a homeless man. Giving money away to complete strangers – downtrodden or not – is not one of my things. What makes it stranger is that I talked to the guy for ten minutes or so while waiting for my train in the subway station. Even stranger, still, is that I actually felt bad for the guy – again – VERY much not me.

It all started when I got into the station. I always walk to the center of the platform so I can get off the train in front of the turnstiles after I get to my destination. It was crowded but I was still able to get a seat on the benches. I sat down and got out my Blackberry and began playing the Brick Breaker game they include with it. Suddenly, an E train pulls in and the platform clears as everyone who travels to Penn Station got on. I had the entire set of benches to myself when this guy who, from the corner of my eye, looked like homeless person.

I’m sorry if I’m stereotyping here when I say the guy looked homeless but its kinda hard to describe it any other way. He swaggered a little – not like he was drunk or on drugs – but like he was slow (in the dexterous sense) and, perhaps, physically challenged because of an injury. His clothes were dirty as was his face. Even with his medium-dark African American complexion, it was easy to see that he wasn’t hygienic. The real give away (in my mind) that made me think homeless is that he talked to me as he approached me but it didn’t make sense. He mentioned that I should smile (another thing I don’t do often) and that I should not worry about my email so much.

The last one struck me as an odd thing do say. How would he know about Blackberries if he was homeless and, presumably, crazy?

He sat right next to me but I ignored almost everything he said – something most New Yorkers do when near or confronted by a homeless person – just in case they are provoked into random acts of violence because of what one says or does around them (people also being scared of those they don’t understand and, therefore, protective of their words). But even with me ignoring his statements, I couldn’t avoid his question. It was simple and from his tone of voice, felt honest, sincere, and heartfelt. In fact, the tone of his voice made me think he was heartbroken. And I was captivated at what he said and they way he answered my questions of him.

What was the question he asked me? He asked if I would by a “paper” from him for $1.50. That’s it! But the paper, he quickly went on to say, is a little business he created to help make enough money to pay for a night’s stay at a very modest shelter not run by the city. He told me that he buys these papers for 50¢ and resells them for a $1 profit for him to get the $20 he needs for this shelter and, if he has anything else, food. I didn’t look at this paper so I couldn’t tell if it was something he printed somehow or if it was printed for him as part of some volunteer group’s attempt to help the homeless fend for themselves.

Being very leery of this person already, I was a little nervous striking a conversation with him but, again, his tone of voice made him sound desperate. But I asked him where he got these papers, where the shelter is, and why doesn’t he go to a free shelter run by the city. Amazingly, he answered every question quickly as if he wasn’t lying or really researched and practiced for this acting gig. I gave him the benefit of the doubt and believed he was being honest still not sure if he could become violent at any moment.

I asked him how he became homeless and if he had any family. He said his mother had passed away many years ago and he has no idea who or where is father is. His former home? It burned to the ground, he said. Again, the emotion in his voice sounded very true and although I never made eye contact with him, I could have swore he started to choke up as if he was about to cry.

So I suddenly went from being afraid of this guy to understanding more about his situation and growing less afraid as the minutes went by. I learned how he lost his job because he couldn’t maintain his appearance after he lost his home. I learned that he was stabbed at the city-run shelter once and never went back. He also told me about his dream which I’ll get to in a bit.

Now I don’t know what kind of job he lost. I’m sure, however, that there are jobs that would take a willing worker without caring what they looked like or how badly they smelled. There are a lot of tough, gross, (possibly) dangerous jobs in the city that must be done for the rest of us to go about our day in that oh-so-familiar level of comfort. The garbage has to be collected, waste removed, chemicals cleaned, rats exterminated and so forth. Sure, they are low paying jobs – and they suck – but when you have nothing… even a shit job is a job that pays more than nothing.

After he obliged me and told me his life story and all its misery, I felt compelled to buy one of his newspapers. I wouldn’t read it. I wouldn’t do the crossword puzzle. I’m sure there wasn’t any Op Ed pieces to think about either. But I wasn’t about to leave the guy empty handed knowing what his dream was and what he had been though and will go through for who knows how long. But I didn’t have those small bills he was looking for; I doubt he was in a position to make change.

So as my train pulled into the station, I reached into my suit pocket and grabbed the only bill I had – a Hamilton. Hamilton…illegitimate child, West Indian immigrant, successful businessman, banker, industrialist, writer, patriot, founding father, Federalist, King’s College (now Columbia University) graduate, martyr, and devout New Yorker. Its actually fitting. Hamilton graces the $10 bill – the decimal system’s equivalent in monetary terms. The reminder that out of bankruptcy, anyone – like Alexander Hamilton – can rise above it all and be very successful. I’m hopeful that the homeless man can be like him.

Just before I gave him the money, though, I told him find a way to get those things he needed from the city. 311 or ask around for some place that will let him clean up safely and often so he can maintain a job; I told him there has to be a way for him to get back on his feet. He didn’t even have a chance to thank me (not that I needed it); probably didn’t even know how much I gave him until the doors had closed on me and I was whisked away to the next subway stop.

What was his dream, you ask? It was to work enough so he could go back to school and become a civil engineer.

I hope he gets there. Its a dream I wish everyone had.