This paper examines the semantic shifts associated with the term “khalīfa” in Qurʾānic exegetical literature (tafsīr) from the “Sunni Revival” of the late Abbasid period (fifth/eleventh and sixth/twelfth centuries) to the early Mamluk period (eighth/fourteenth century). Emphasis is given to Sunni commentaries on verses 2:30 (the “Adam verse”) and 38:26 (the “David verse”), supplemented by commentaries on other verses containing derivatives of the root kh.l.f. (“khulafāʾ,” “khalāʾif,” “khalafa,” and “istakhlafa” among others). I argue that beginning in the late Abbasid period, the Qurʾānic “khalīfa” was increasingly identified with the historico-political caliph, as individual exegetes—al-Ṭabarī (d. 310/923), al-Māwardī (d. 450/1058), al-Zamakhsharī (d. 538/1144), Ibn al-Jawzī (d. 597/1200), Fakhr al-Dīn al-Rāzī (d. 606/1209), al-Qurṭubī (d. 671/1272), and Ibn Kathīr (d. 774/1373)—introduced new clusters of political vocabulary associated with the caliphate in legal (fiqh) and theological (uṣūl al-dīn) writings into their commentaries on the term “khalīfa.” Especially with regard to the Adam verse, exegetes also delineated a sacred genealogy for the caliph stretching back to Adam, who figured in medieval exegetical literature not only as first man, but also as God’s first caliph on earth. This is observed when tafsīr literature is placed in conversation with other genres of writing, such as works of fiqh and uṣūl al-dīn, to demonstrate how assertions made in one medium might complement what is unsaid or unsayable in other mediums. Most scholarly works in recent decades on the Qurʾānic term “khalīfa” hardly examine individual exegetes chronologically, and hence derive a homogenous and general meaning of the term which neglects the diverse vocabulary and expressions used by exegetes in their interpretations of the term. Wadad al-Qadi underscores a different approach in her 1988 article, which she describes as “exegetically historical,” to determine how early Muslim exegetes under the Umayyads understood the term “khalīfa” in their own time and place. I apply al-Qadi’s “exegetically historical” approach to a later period from al-Ṭabarī to Ibn Kathīr, when a more rigid sense of Sunni orthodoxy was being formulated and juridical discourses on the caliphate and public authority were being systematized, by scrutinizing individual exegetes in chronological fashion to examine the semantic and terminological shifts associated with their interpretations of the term over time. Overall, this paper sheds light on how medieval Muslim thinkers attempted to make connections between political reality and the divine word.