After the period 1878-1885, when Bulgaria’s de facto southern border was drawn through Edirne’s backyard, this storied Ottoman city came to be regarded by contemporaries as peripheral and past its prime. But in 1908, the Young Turk Revolution brought new energy to Edirne and its Jewish community. New freedoms of the press and association disrupted power dynamics within the Jewish community and created a public sphere where leaders and intellectuals from the various religious communities could converse. Also in 1908, Bulgaria’s official declaration of independence from the Ottoman Empire gave new meaning to the border and prompted Jewish writers in Edirne to think hard about what Jews in both countries owed to their respective states and to fellow Ladino-speakers—who were often family members—living just beyond the boundary line. Using Ladino newspapers, Ottoman government documents, and French-language letters penned by directors of Jewish schools (among other sources), this paper argues that the confluence of these two events—plus a Jewish population boom—brought political energy to an all-time high in Edirne’s Jewish community. Jews who heeded the new government’s call for integration across religious lines sometimes clashed with those who gravitated toward Zionism, a movement that gained popularity among Ottoman Jews after the Young Turk Revolution. But for reasons related to its history and location, the Jews of Edirne were especially drawn to a middle path, a politics of decentralization that sought to preserve Jewish autonomy while promoting civic virtues vis-à-vis the constitutional state and the local Christian and Muslim communities. Leaders of this camp tended to be savvy upstarts who were fluent in the Young Turk discourse of democracy, liberalism, and integration, even as they championed a form of Jewish politics that was unapologetic in its defense of communal interests. Not only does this paper fill a gap in the scholarship on Ottoman Jews—a historiography that overwhelmingly focuses on port cities at the expense of inland centers such as Edirne—it also helps us understand the processes by which twentieth-century borders were created and the ways in which the latter shaped Jewish life in late-imperial borderlands.