I recently gave a presentation on the American Dream, and why it's a bunch of crap. Salient points reproduced here.
As I see it, and as I often hear it, the American Dream (AD) is that any person, no matter where they start in life, can make it to the top. All it takes is hard work and a can-do attitude, two more of those quintessentially American traits. If we accept this as a fairly good model for the AD, the question then becomes, "Why are there poor people?" We can take the pro-AD answer, which is "They aren't working hard enough" or we can take the anti-AD answer, which is "A person's success or failure in life is determined by things outside of him or her self".
Let's take the first answer first, if only because it's easier to argue against something than it is to argue for it. We can see immediately that it's sort of elitist; it says that if I'm at the top, I'm there because of how awesome I am. The corollary to that is that if you're on the bottom, you're there because you just didn't try hard enough. I say "sort of" instead of "completely" because it depends on who's doing the talking. If a poor person says, "I'm poor because I just didn't try hard enough - I wasted my time doing things that I knew wouldn't get me anywhere in life", then that certainly doesn't seem so offensive. I have my doubts about how many people in poor circumstances would be willing to take the blame.
The other answer has its problems too. First, we have to realize how deterministic it is; essentially, it says that a person's life is decided by factors beyond their control. I don't think there's much argument that we're shaped by our environment, but once you start giving that as an excuse for what the politicians would call "under achievement", it both allows people slack for their failures and reinforces negative self image. But the other critique of that answer is a little more subtle - and it's not a critique of the answer so much as the response to the answer. If the rich help the poor, they're saying that the poor need them, and they're putting the poor in an inequitable position. Not only that, it becomes more about the rich than the poor; we have $1,000 dollar a plate dinners to prevent starvation in Africa, or my favorite, a chalk message drawn on the sidewalk at Harvard proudly proclaiming, "Smores for Darfur, $2".