This thesis illustrates how Pompey’s annexations and organizing of the eastern provinces for Rome were more pragmatic than imperialistic. Greek and Eastern specialists are used in order to give a better back story than the imperialist thesis offers in its reasoning for the annexations. By adding more detail from the Greek and Eastern perspective, other dimensions are opened that shed new light upon the subject of Pompey’s eastern settlements. Through this method, the pirate campaign and the annexation of Syria are greatly developed, especially in concern to changes in culture that Pompey’s settlements forced. The culture of piracy and banditry were curbed by the eastern annexations. In Syria the Greek settlements were revived and protected from the expansion of Arab and Jewish dynasts. Considering the annexation of Pontus, a more detailed analysis on the lex Pompeia and the new taxation system is developed, which questions parts of the imperialist thesis especially in regards to role of the publicani. Graeco-Roman cultural spread is also developed in the Pontus chapter to show some of Pompey’s motives. Previous works are expanded upon and synthesized into this work, the aim being to reconcile some of the arguments, concluding with the proposition that Pompey, his efforts, and his settlements, were more pragmatic than imperialistic