The seminal book in the field; the one that started the modern welfare reform debate. Some of the figures might be dated, but the reasoning is as fresh as ever.
Yes, she's a lefty (favoring a guaranteed national income among other things), but you won't find a better testimony to the degradation of contemporary welfare.
A ground-breaking history of private charity in America and why it is superior to government-run welfare. Sometimes a bit heavy on the religious content, but still one of the best defenses of civil society as an alternative to welfare.