When it comes to charity, I guess he's one of those "eliminate the middleman" guys, prefering to assist the afflicted without spending money on administrative costs. At least we know he has a heart.
Or this is another story entirely. For fun he takes all his money and gives to a bum, amd then one of dad's snipers takes out the drifter, and when the police come he says it was robbery and of course everyone believes him.
Richie is looking for the barrel of the rifle to appear out the window above. This is his favorite part.