This dissertation examines Gürcü Osman Pasha, who was a promising military origin Ottoman state official at his early career stages, but then turned into a rebel sacking Rumelian districts in collaboration with the most unruly figures of the region. When his political, military and financial sources of power eventually evolved to pose a significant threat to the central authority, he ended up being executed by the government. Although he was not a primary figure of his time, both his political networks and dynamics of his rebellion refer that he had strong connections with many prominent characters of the period. Through analyzing reasons behind Osman Pasha’s rebellion, his patronage relations, alliances and conflicts, the dissertation depicts the volatile and delicate structure of the early modern Ottoman politics and places Osman among other prominent characters of the time. It also focuses on formation of Osman’s household and his various revenue sources, discussing how they enabled him to become a prominent pasha without a powerful family, or a local notable origin, or a considerable wealth of his own at the beginning of his career. As a conclusion this study attempts to explain Osman Pasha’s career cycle with a vicious circle of acquiring power, behaving disorderly and power again, and so on. It also offers a principle that might help us comprehend the dynamics of the Ottoman politics and the shifting power from the center to the provinces and vice versa.