This paper situates Paul’s language of πίστις in its first-century CE Greco-Roman political context. Together with δικαιοσύνη, πίστις carries social, political, and legal overtones, directing human-divine relationships. I argue that Paul’s language of πίστις in Romans relates to the defense of God’s δικαιοσύνη as part of an underlying theodicy motif. Within this framework, the Christ is given as a pledge/assurance (πίστις) to demonstrate God’s δικαιοσύνη, which vindicates and confirms God’s commitment to his πολιτεία with Abraham. After sampling πίστις in Greco-Roman political contexts, I offer a comparative analysis of Romans 3:22-26, suggesting that the revelation of the δικαιοσύνη of God “διὰ πίστεως Ἰησοῦ Χριστοῦ” (3:22) refers to God’s own πίστις, as his pledge/assurance by which he demonstrates his δικαιοσύνη. This reading is further supported by bringing Josephus and Isaiah 42:1-6LXX into dialogue to suggest that Paul contextualized the language of διαθήκη for his Greco-Roman auditors. Though others have noted the theodicy motif in Romans (R. Hays 1989; R. Watts 1999; J. Kirk 2008), this paper advances the contributions of T. Morgan (2015), S. Sierksma-Agteres (2015), and N. Gupta (2020), insisting that Paul’s language of πίστις should be appraised at the intersection of Israel’s scriptures and his Greco-Roman context, possessing relational, political, and theological signification.