This paper will attempt to discuss recent developments in the comparative study of the Ottoman Empire by examining its alliance with a number of overlapping yet different readings of the Mediterranean. At various points, and stemming from diverse contingencies, the Mediterranean has been explored as a topical cradle of historical meaning, inspiring a number of different understandings of the regional, the peripheral, the collective, and the comparative. From the second generation of the Annales school, in the post-war period, to the booming of postcolonial studies in the post-cold-war era, the history of the Eastern Mediterranean, in particular, has emerged as mirror of highly loaded methodological debates. In this context, the study of the Ottoman periphery has contributed a wide range of perspectives vis-à-vis mobility, connectivity, and fluidity in the plurality of Ottoman (and post-Ottoman) Mediterranean worlds. This paper will discuss the potentials and limitations of this growing literature together with the interrelated contexts of its creation. Building on both inclusions and exclusions, the analysis shall address why certain comparisons seem to be more preferable than others. Moreover, it will explore the connection between new framings of the region and recent developments. The rise of an allegedly moderate new regime of political Islam in Turkey; the profound socioeconomic crisis in the Mediterranean periphery of the EU; and the dangers and promises fostered by the Arab spring merge over the Mediterranean both as emerging new realities and as evolving novel concepts. To what extent does this fusion form new bridges between existing normative categories—such as West and East? And what are the resulting new boundaries?