This study investigates the rhetorical orientations of two major figures in Arabic rhetorical thought—Al-Sakkaki (d. 626 AH) and Al-Qazwini (d. 793 AH)—through a comparative analysis of Miftah al-Ulum and Al-Eidhah. Both scholars shaped the intellectual foundations of Arabic rhetoric, with Al-Sakkaki’s Miftah al-Ulum serving as the pivotal source from which Al-Qazwini drew in formulating his systematic tripartite classification of rhetoric into Elm al-Ma’ani, Elm al-Bayan, and Elm al-Bade’a. The research adopts a comparative analytical approach, examining Al-Sakkaki’s scientific and comprehensive vision characterized by structural coherence and intellectual inclusivity, alongside Al-Qazwini’s pedagogical, emotional, and religious orientations. The findings reveal that Al-Qazwini’s work was deeply influenced by Al-Sakkaki’s rhetorical principles, while Al-Sakkaki’s project stands out for its conceptual depth and systematic methodology, viewing rhetoric as part of a broader literary and linguistic science. The study highlights the continuity and divergence between both scholars’ rhetorical perspectives, affirming their lasting impact on the formation of Arabic rhetorical theory.