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This dissertation argues that Horace’s engagement with philosophy in Epistles I is deeply rooted in the Epicurean philosophical tradition. During the 1st century BCE, Epicureanism had a significant presence in Rome, particularly within a community near the Bay of Naples, where the Epicurean philosopher Philodemus of Gadara was a prominent figure. Philodemus’ ethical treatises serve as an essential source for Horace. While this connection has been studied in relation to the Satires, it has not been explored in the Epistles. In his moral instruction, Horace not only draws upon the ethical teachings of Philodemus but also patterns his identity on the model of the Epicurean sage. In the treatise On Property Management, Philodemus depicts the sage engaging in moral instruction and receiving financial support from students within a framework of friendship and generosity. Horace adopts this framework in the Epistles, as he offers advice to a group of friends that includes his patron Maecenas. In so doing, Horace attempts to redefine his relationship with his Maecenas, emulating the friendship between the Epicurean sage and student. Additionally, Horace borrows from Philodemus’ On Flattery and On Frank Speech to offer a critique of the Roman patronage system as promoting the behavior of the ancient Greek kolax (flatterer). Horace carves out a new identity in his relationship with Maecenas, framing their connection as an equal friendship in which each contributes in distinct ways.