Coupla years ago for new years I went out with some folks in Philly. We went to Maggiano's and had this huge ass dinner for 10, drank who knows how many bottle of wine, and dropped a bunch of cash. We had lots and lots of leftovers. After that we took the subway over to the waterfront to catch the fireworks. There was this bum in the station, just kinda sittin along the wall. We gave him all our leftovers and said, "happy new year man."
I really do try and help people out when I can. The thing is, I see the same people living on the street coming up to me asking me for a buck or whatever. There's this one bum dude, I called him sales pitch bum. He had this rehearsed script, like, "even if you only spare a quarter or a dollar or whatever you can do, it would be most appreciated," actually I forget what the actual pitch was, just that he sounded like a telemarketer. I ain't seen him lately but I definitely would keep bumping into the guy over several years. He'd do his sales pitch in the daytime and then I'd see him at night stumblin around with other bums drunk off his ass with the money he got from oversensitive college kids.
Then you got your plain greedy bums. Last weekend I was walking to the bar, this bum comes up to me tellin some story bout how he's tryin to catch a cab or a bus or whatever. I ask him how much money he's got, he says 3 bucks. I tell him smallest I have is a 5, so if he gives me his 3 I'll give him my 5. He whips out 2 singles and holds on to em really tight. I hand him the 5 anyway, he starts to hand me the 2, but when I put my hand on em he doesn't let go. I say hey man, you're making 3 bucks here, you're getting better than our deal. Finally after some more tugging he lets go.
Even though stuff like this tests me, if I had enough money such that money didn't matter to me any more, every single bum who asked me for somethin I'd give 50 bucks. Charities are great and everything, but when a bum comes up and asks for money and you help em out you're making a difference to that one person at that particular moment. Yeah they could be running a scam, but on the off chance they're not I don't want to withold my generosity.