Even those who messed up here and there could deserve a leg up once or twice. But, first of all, this is something best done locally, where folks know one another well and can distinguish between bona fide generosity and generosity to a fault, the wasteful and useless variety. There is absolutely no justification to believe that the poor are all virtuous, while the rich are bastards. That is just plain nonsense, a form of scapegoatism no less insidious that blaming everything on Jews or blacks or farmers. Yet another vital point on this score is that the unconditional devotion of one's life to those who are poor and needy refuses to recognize the plain humanity of these folks, a humanity that makes them just as capable of doing things wrong as those who are not poor.
People can make choices, even if their options are few.
And some of these choices will be wise and prudent, others reckless and negligent. And the results will reflect on the quality of character behind these choices. To declare that all is equal, that everyone must be treated as if no differences in character and performance existed among people, is to deny a crucial element of our humanity. It is also interesting to note that the very people who tell us that everyone is equally deserving of love and, of course, other people's resources are also unhesitatingly critical and contemptuous of those who disagree with them. Suddenly these folks could help what they do, or at least what they think, and if they think the wrong thing, they shall be shown no mercy at all.