Ben Sira’s “Praise of the Fathers” has generated much scholarly discussion regarding the larger purpose of these chapters. This paper will argue for a greater hortatory emphasis in Ben Sira’s assessment of these heroes from Israel’s past than many commentators have allowed. While the sage clearly intends to offer an encomium of major figures, including Simon II, prominent themes from earlier in the instruction, such as a good name, pride, honesty in the marketplace, allegiance to the Torah, and respect for the priesthood, are key elements in this section. This paper will pay close attention to the selective manner in which Ben Sira reads the Deuteronomistic History, Chronicles, and other sources in order to laud these individuals from Israel’s past and implicitly encourage faithfulness to their example. Our comparative approach will illustrate some of the differences between retrospective praise in a wisdom text and what appears in historiographical literature. The discussion will also take up other examples of this type of praise, including 1 Macc 2:51-60 and Hebrews 11, to show parallel aspects of this type of recall. By pointing to the creative manner in which this sage uses these figures in the service of his own aims, the paper will show the parenetic value of this section and Ben Sira’s allegiance to the emerging narrative of Israel and her most praiseworthy heroes.