This essay considers a comparative exploration of divine inspiration in Hellenistic Jewish thought through an analysis of two key works by Philo of Alexandria, namely "De Somniis" and "Legum Allegoriae," in comparison with the Pauline corpus. Emphasizing the thematic elements of allegorical interpretation, the role of the Holy Spirit, and mystical dimensions inherent in these works, the study seeks to understand the Hellenistic Jewish speculative tradition as related to “divine inspiration.” In "De Somniis," Philo delves into the significance of dreams as a mode of divine communication, showcasing a nuanced understanding of inspiration that extends beyond wakeful revelation. "Legum Allegoriae," with its intricate allegorical interpretations of the Hebrew Scriptures, emphasizes the hidden wisdom concealed within the literal text. The Pauline corpus shares a similar philosophical outlook, where at points he discusses (indirectly) divine inspiration, the agency of the Holy Spirit, and employs allegorical interpretations. The comparative analysis scrutinizes the rhetorical strategies and literary devices employed by both Philo and Paul, demonstrating the intersections of their philosophical backgrounds contemplating their shared Hellenistic milieu, which influenced their perspectives. The study aims to shed light on how both Philo and Paul work within the same speculative tradition and how each author adapted such notions for their own respective theological endeavors. This essay contributes to a broader appreciation of the shared philosophical, theological, and mystical underpinnings of divine inspiration in Hellenistic Jewish thought and early Christian literature.