Students of poverty in Jewish, Christian, and Muslim social, literary, and legal contexts in late antiquity and the Middle Ages have noted the phenomenon of wealthy people who fall into poverty and the provision of charitable assistance to them. This essay's principal purpose is to point out an important difference between the development of attitudes toward the formerly wealthy poor in rabbinic literature of late antiquity and in other religious and legal contexts. Peter Brown notes evidence of late Roman empathy for the wellborn poor, hypothesizing that this empathy can be attributed to a desire to preserve these remnants of the old, proud plebs romana in the uncertain sixth century. Ingrid Mattson demonstrates that between the eighth and tenth or eleventh centuries CE, Islamic jurists moved in the direction of taking the “social and economic context” of a poor person into account in determining that person's legitimate needs. By contrast, as this essay will show, rabbinic literature of late antiquity moved in the opposite direction, from third-century empathy for the formerly wealthy poor to growing ambivalence in the fourth through the seventh centuries.