Past scholarship on πίστις in Hebrews has tended to interpret it as “faithfulness” rather than “faith,” (e.g., Grässer, Dautzenberg, et al.) thus reducing the appreciation for the propositional (“belief”) dimension and elevating the focus on πίστις as behavioral, i.e., πίστις as perseverance. This view is seemingly buttressed by the warning passages, which warn of apostasy and exhort to “πίστις.” This study argues that the contextual re-use of Old Testament passages adduced in the warning passages is an underappreciated lens for understanding the nature of πίστις in Hebrews. Using Hebrews 10:36-39’s use of Isaiah 26:20(LXX) and Habakkuk 2:3-4(LXX) as a test case, it is argued that the author of Hebrews, like Isaiah and Habakkuk, expects a discriminating judgment that will separate the righteous and the wicked, judging the wicked and rewarding/vindicating the righteous. The author’s exhortation to πίστις is an exhortation to faith in the reality and truth of the coming judgment, contrasted with scoffing disbelief; a propositional belief that leads to perseverance in the face of hardship.