The Nabataeans, best known today for the spectacular remains of their capital at Petra in southern Jordan, continue to defy easy characterization. Since they lack a surviving narrative history of their own, in approaching the Nabataeans one necessarily relies heavily upon the commentaries of outside observers, such as the Greeks, Romans, and Jews, as well as upon comparisons of Nabataean material culture with Classical and Near Eastern models. These approaches have elucidated much about this enigmatic civilization but have not always fully succeeded in locating specifically Nabataean motivations and perspectives within and behind the sources. To address this lacuna, my dissertation provides a critical re-reading and analysis of the ancient evidence, including literary, documentary, numismatic, epigraphic, art historical, and archaeological material, in order to explore the Nabataeans' reaction to, effect upon, and engagement with, historical events and cultural movements during the period from 312 BCE, when the Nabataeans first appear in the historical record in the wake of the conquests of Alexander the Great, to the annexation of their territory by the Romans in 106 CE. I seek to properly acknowledge the ways in which the Nabataeans self-consciously shaped their own political and cultural destinies while interacting with the broader Mediterranean and Near Eastern worlds. While identification, analysis, and articulation of the Nabataean viewpoint guides the dissertation, the project also broadly challenges or qualifies several important assumptions about the Nabataean civilization. In treating the period from 312 BCE to the eastern settlement of Pompey in 63 BCE, I argue that the Nabataeans played a more important role in the Hellenistic world than has generally been acknowledged--especially for the 3rd and 2nd centuries BCE--and I articulate the nature and significance of their position vis-à-vis their neighbors and rivals, both regional and further a-field, specifically from the Nabataean point of view. This analysis makes an important contribution to current discussions of the development of Nabataean identity and culture, and it can serve as a model for viewing other under-explored Hellenistic civilizations in the Near East. Events in the ensuing period, after 63 BCE, take place under the broad shadow of the extension of Roman power in the eastern Mediterranean, but by analyzing internationally important events of this period, such as the Roman expedition to Arabia ordered by Augustus, from a specifically Nabataean vantage point, I am able to show that the Nabataeans' self-interest often did not align with Roman objectives, and that their foreign policy flourished on its own merits. These conclusions appropriately acknowledge Nabataean individuality and autonomy, challenging the widely asserted notion that Nabataea fits a prescribed model of a client--or dependent--state of Rome. In examining the last generations of Nabataean independence, I argue against the traditional characterization that sees during these years a gradual political, economic, and cultural decline for the Nabataeans, culminating in their annexation by the Romans in 106 CE. I demonstrate that the period instead represents a time of increasing sophistication and self-confidence on the part of the Nabataeans, not one of resignation or submission to the inevitability of Roman domination.