Years ago: no.
Years ago, I heard a piece on the radio driving to work about giving money to panhandlers. The story's main point was that some huge percentage of panhandlers were going to turn around and use that money to buy drugs or alcohol. So, I believed that giving a homeless person money would actually hurt them more than help. I felt uncomfortable passing by someone asking for money on the street and not giving them something, but at least gave them respect by looking them in the eye and saying, "sorry, but no."
Then I stopped working in Boston. I stopped running into panhandlers quietly saying "spare change" as I walked down a sidewalk because you don't see that kind of thing where I lived in an affluent suburb outside of Boston.
Now, we live in Worcester. During our first winter here when Skip and I were out one evening, we stopped at a convenience store. Man, it was cold that day. When I got out of the car, I found huddled in the parking lot a young, homeless man and his 2 dogs. He asked me for money ... how could I refuse? I gave him $10 and we chatted briefly about his dogs. I felt good, feeling that I was helping him and his dogs. Hoping he'd be okay, that they'd all be okay, and that they'd all get something to eat because of my gift. Skip, too, thought it was great that I'd given him some cash.
I couldn't stop thinking about that young man and his dogs. Over the next few weeks, I drove around in the area of that convenience store, hoping to find him and see that he was all right, give him some more money, pet his dogs. Not surprisingly, I was never able to find him.
But that encounter changed my attitude about panhandlers; I wanted to help them directly. You often see homeless folks with cardboard signs asking for money at many streetlights around the city. If I stop at the light and there's sufficient time to give them so dough, I do. They are always appreciative, thanking me and saying "God bless you" (being an atheist, I could live without that, but I understand where it's coming from). Sometimes we have a minute to chat before the light changes.
So maybe some of that money does go to drugs or alcohol, feeding the addiction. But I know some of it goes to food or shelter or other necessities of life lacking for that soul. Were I to make a donation to a charitable organization helping the homeless, I know some of it, perhaps a lot of it, would be siphoned off for fundraising costs, administrative costs and so on. Here, the $10 or $20 I pass out the window of my car goes right to one person who needs it.
There are far too many homeless and with milder weather upon us, I see more and more of them. I wish I'd never see a cardboard sign asking for money again. But, as long as I do, I'm willing to help. I have so much, why not pass on a bit to those who need it far more than me?