The article’s point of departure is a debate that took place in about 1290 between Zeraḥyah b. Isaac Ḥen and Hillel b. Samuel, two Jewish-Italian thinkers, that presents us with a surprisingly great variety of Arab, Jewish, and Latin-Christian exegetical and cosmological approaches regarding angelic nature. Zeraḥyah, following the dominant attitude among Arab, Muslim, and Jewish philosophers, strives to interpret the biblical angel-figure either naturalistically or allegorically. Conversely, Hillel cleaves more closely to Christian scholastic conceptions, adhering to the biblical narrative in the literal sense. The struggle between Jacob and the angel (Gen 32) posed one of the most challenging cases, presenting the interpreter with a situation in which an angel did not only appear but was also engaged in bodily contact. In the case of Hillel, his dual commitment as a Jewish Maimonidean heavily influenced by Latin Scholasticism led to the development of a highly unique solution.