The question of Christian almsgiving in late antiquity is one that has received fresh treatment recently in Richard D. Finn’s monograph, and the issue of wealth and poverty in this period is the subject of a number of current international scholarly projects. This paper considers the place of almsgiving in Jerome’s vision of asceticism found in his advice to wealthy Christians. When one reads Jerome’s letters to Furia (Epistula 54), Lucinius (Epistula 71), Oceanus (Epistula 77), Salvina (Epistula 79), Eustochium (Epistula 108), Julian (Epistula 118), Ageruchia (Epistula 123), and Demetrias (Epistula 130), where the parable of the wily manager (Luke 16:9 in particular) is employed, as well as in other letters containing ascetical advice that do not employ the parable, it would be easy to conclude that the purpose of almsgiving for Jerome was soteriological self-interest. It will be argued here that to reach such a conclusion would be to fail to appreciate his rhetorical strategies employed in these letters addressed to wealthy Christians. Jerome’s vitriolic treatise Contra Vigilantium, written for a different kind of audience and with a different purpose in mind, as recently investigated by David G. Hunter, also contains references to almsgiving. In it the poor are not simply the objects enabling the wealthy to be saved but are considered in terms of social justice and equity as subjects whose needs must be addressed.