Intellectuals have sought and continue to seek to influence the political conditions of their time. In the endeavor of moral correction of the ruling class and influencing political decisions, these thinkers must, on the one hand, overcome the risk of corruption or co-optation by the ruling elite, and on the other hand, the danger of rejection, exile, and execution. In classical antiquity, Plato’s unsuccessful endeavor to convert Dionysius II, the tyrant of Syracuse, into a philosopher-king is particularly notable. Like Plato, his contemporary Isocrates, a rhetoric teacher (436-338 BC), sought to influence the politics of his time by writing letters to Greek autocrats, nine of which survive. This work provides a new German translation, a commentary on the singular letters as well as interpretive essays that place the texts within their literary and historical contexts. As has been shown, Isocrates introduced the letter, previously a tool of commercial exchange, as in literary genre into Greek prose. By the use of the rhythmical and periodical style of his speeches, Isocrates encouraged his recipients toward an enlightened despotism, distinct from tyranny, and advocated for a pan-Hellenic foreign policy. It has been demonstrated that his endeavors to offer political guidance remotely, rather than through conventional courtly channels, yielded only limited success. More importantly, Isocrates used his letters to introduce and endorse his students and associates as authorities and advisors to contemporary rulers, thereby expanding his interpersonal Mediterranean network.