This dissertation explores the theological and social dimensions of generosity in the book of Sirach and contextualizes them within Second Temple culture and thought. After necessary prolegomena, the work begins by exploring the role of wealth and poverty in Ben Sira's thought and concludes that the dissonance between the principle of retributive justice and the social realities of Seleucid Judea provides the essential matrix in which his understanding of generosity is situated. In chapter 3, the role of generosity is correlated with Ben Sira's belief in the finality of death. Through an exegesis of Sir 14:3-19 it is argued that, unlike other Hellenistic works, Ben Sira integrates the topic of generosity into the motif of carpe diem. Thus, giving generously to others actually contributes to "the good life." Chapters 4 & 5 provide an exegesis of Sir 29:1-20 on the topics of loans, surety, and almsgiving. Ben Sira displays an innovative approach to surety. By subsuming both loans and surety under an ethic of mercy, they become essential components of the financial dealings of a Wisdom-Torah piety. Almsgiving transcends normal economic dealings and can be trusted to bring a greater return from God. The fundamental theological logic at work consists of viewing the poor as proxies for God and is based on the economic structure of Prov 19:17. Chapter 6 takes up the relationship of almsgiving to sacrifice and argues that they are both integral to Torah obedience because both the poor and priests are understood as proxies for God. These two services to God cannot be set in opposition, even though pragmatically they would have been in some tension in the social climate of Ben Sira's time. Ultimately, both derive from the actions of Wisdom herself and so represent an ethic of imitatio sapientiae. Chapter 7 explores the extent of almsgiving and argues that the tension between limited charity (12:1-6) and inclusive charity (4:1-10; 7:32-36) is resolved by recognizing that almsgiving is an act of imitatio Dei. The tension, therefore, derives from the more fundamental tension involving the principle of retributive justice.