Using Richard Hays’ criteria for intertextuality, this paper examines the likelihood of a reference to Sirach in Hebrews. While the criteria are not resoundingly in favor of an intertextual allusion, they do likely suggest a relationship, albeit a highly complex one. In order to understand this relationship, this paper considers the overlap of themes and vocabulary. More importantly, however, there exists a likely relationship between Sirach’s example list (Sir 44:1–50:29) and Hebrews’ (Heb 11:1–12:4), both culminating in an archetypal figure, Simon son of Onias in Sirach and Jesus Christ in Hebrews. Nevertheless, the two possess formal differences in the two documents. In particular, the differences extend to their respective ideologies about the priesthood. While Sirach is positive towards the priesthood of his day, Hebrews is pessimistic about the Aaronic priesthood. This might be explained by different readings of the prophetic tradition of critiquing the priesthood or by historical location. Most importantly, however, the ideological dissonance must be explained by the convictions of the author of Hebrews considering the person and work of Christ. We conclude then, that while there was a relationship between the two, we must qualify that relationship with respect to the complexity of any allusion. This relationship is complicated by canonical logic; Hebrews neither blindly affirms Sirach nor blithely rejects it. Rather, he appropriated it in a careful and nuanced manner, appropriate to an apocryphal book.