On the commemoration of five centuries after the death of Romanian Ruling Prince Neagoe Basarab (1512-1521), one of the most important representatives of cultural resistance on Romanian territory in the Middle Ages, the author of the present paper shines a light on the history, context and influences of his masterpiece, The Teachings of Neagoe Basarab to His Son Theodosius. Thus, the paper highlights Neagoe Basarab’s prophetic side, how his writings bring education to his people or the influences of authors like Basil I the Macedonian or Constantine Porphyrogenites on his style and ideas. At the same time, due attention is given to the influence of his work of patristic voices such as St John Chrysostom, Dionysius the Areopagite, John Climacus or mystical authors such as Varlaam și Iosafat, to his way of thinking, and the metamorphosis of his ideas. Furthermore, potential influences such as the one of Machiavelli and his chief work, The Prince, are also brought to attention in the paper, emphasising that there are voices that persist in the claim that the Italian author may have influenced Neagoe Basarab’s activity. The paper concludes, among other things, that, through his work, Neagoe Basarab managed to pave the way for Humanist culture on Romanian territory.