This article examines the lives of three politicians from Austria’s crownland of Bukovina—Aurel Onciul, Nikolai Wassilko, and Benno Straucher—who pursued distinct national ambitions and built successful political careers as advocates of democratization and nationalization under imperial rule. It aims to highlight the multiple transitions these individuals experienced, including shifts from conservative to democratic mass politics, struggles for national rights, and the passage from imperial to national orders. After 1918, Onciul became a representative of a nationality with its own nation-state, while Wassilko and Straucher became spokespersons for embattled minorities. All three struggled to adapt to the new national order, and the forces of nationalization they once championed ultimately turned against them. The article argues that the nationalist politics that had brought these politicians success under imperial rule were later criticized by their co-nationals as treasonous and opportunistic, illustrating the complex and often paradoxical outcomes of nationalization processes in Central Europe.