The Republic of Turkey sits at a crossroads between the East and the West, and has long been divided between two very different worlds. Relations between Turkey and the European Union are founded upon a complex history of both shared and divergent political and social values. Thus, the question of Turkish accession is complicated, mired in a maze of mutually important geopolitical, economic, cultural, and diplomatic issues. Both the cultural and political arguments concerning Turkey’s candidacy must be placed within the context of the accession process and the weaknesses of the EU’s enlargement strategy. In light of contemporary scenarios, Turkey's compatibility with the EU is examined, based upon the hypothesis that there is little tangible theoretical or analytical support for some of the arguments used to evaluate Turkey’s petition to join the Union.