In fifteenth-century Italy, following an unprecedented engagement with Latin sources, the discussion of rhetorical and poetic language became the meeting point between the medieval Aristotelian tradition and contemporary Humanism. In The Book of the Honeycomb’s Flow (ספר נפת צופים), printed in Mantua in 1475/76, Yehuda Messer Leon (c. 1420/25-c. 1498) was the first to combine Aristotle’s Rhetoric interpreted through Todros Todrosi’s Hebrew version of Ibn Rušd’s Middle Commentary with sources used by the contemporary humanists such as the Ciceronian De inventione, the pseudo-Ciceronian Rhetorica ad Herennium and Quintilian’s Institutio Oratoria. Messer Leon not only proposed an original model of exegesis, where the rhetorical method is applied to the Holy Scriptures, but he also offered an original theory of poetic imitation. Starting from Yehuda Messer Leon’s notion of metaphorical language, this paper focuses on the role of literary imagery and poetic invention in one of his most renowned students: Yoḥanan Alemanno (1433/34-1504). Following Messer Leon, Alemanno considered rhetoric and poetic language central in both his works and his educational programme. Finally, this paper intends to stress the importance of the discussion of literary style and poetic language in the wider framework of the fifteenth-century Florentine cultural environment.