I've written about this before and it's something that I never quite get used to, although after working in Chicago for 14 years one would think I wouldn't even notice anymore.
I don't know what the PC term is, but I usually say panhandlers. These are the people that hang around outside asking for money. Some hold signs, some stand wordlessly with plastic cups in their hands, some drone on like carnival barkers "spare some change t'day?" others stand or sit in the midst of the commuter route which forces the throngs to either see them or trip over them. Then there are the ones that bring their children with them which is particularly heart breaking. The one woman I see frequently always has very nicely dressed children, so that gives me some comfort that they are being cared for.
There are the regulars that I get used to seeing every commute into the office and every commute out to the train; if they aren't there I notice it. Two of these fixtures outside Union station are the elderly African-American man (he puts up a sign in July on his birthday which last year said he was 91 years old) and an older, hunched over Caucasian woman. They each stake out their respective territories; she holds her Streetwise magazines for sale and sometimes can be seen sitting and reading. He wears dark glasses (for the longest time I thought he was blind but have since figured out he is not) and has perfected the art of sleeping sitting up straight in his chair; now I know why he wears the dark glasses. They are both at their stations pretty much daily, regardless of weather.
I noticed three new faces these last few weeks. One was a nicely dressed woman in her 50s. She wore a hat and held a sign that read "Lost my job, behind in my rent". She placed herself in front of a large utility box, maybe as a wind break or maybe to give herself a place to lean against. She was carefully made up and stood motionless, not saying a word. The first time I noticed her she startled me because she was so very still until I met her gaze and she looked at me hopefully with her dark brown eyes. She had a purse and a carry-all bag next to her, one that she may have used when she was still employed. Something about her eyes and her quiet grace stuck with me.
Further on my commute, next to a Starbucks, was a young man who also held a cardboard sign. His said "Out of work. I just want to feed my Family". He had underscored the word "Family" three times. He didn't say anything as he stood there, shifting his weight from foot to foot, but he had a nice smile, a hopeful smile on his face, as he tried to catch someone's eye.
Then there was the older gentleman with the sign that said "Need to pay for daughter's graduation/prom". This almost made me stop and say "are you kidding me? Really?" Then I thought, "well, at least he's honest".
After passing the quiet, dignified woman for several days I decided I would give her some cash. It wasn't much, but I folded up a $5 bill and put it in my coat pocket so it would be easy to get to when I saw her. But she wasn't there. She wasn't there the next day or the following day either. I wondered if she was OK and even thought that maybe she was able to find work and didn't need to ask for help anymore.
So today I walked with my $5 bill to the young man that just wanted to feed his Family. I approached him and as I took my hand out of my pocket, he extended his. I touched his hand and put the bill in it; he smiled and said "thank you, thank you". I smiled and kept walking. I heard him pause behind me and then call out "thank you so much!". As I walked I imagined him gathering up the money he collected today and going to the store to buy groceries. I hope that is what he is going to do and I wish him the best of luck.