This chapter outlines the rationale for selecting Hungary and Macedonia as the book’s central comparative cases. Both are parliamentary democracies that underwent successful democratization before entering sustained periods of autocratization, yet they differ significantly in their historical trajectories and international integration. Hungary joined the European Union in 2004, while Macedonia remained outside both the EU and NATO during its authoritarian turn. The “most different systems design” allows for examination of how similar patterns of democratic erosion can emerge under contrasting structural conditions. The chapter first sets out the methodological approach, combining process tracing with historical institutionalism to capture the interaction between formal and informal institutions, and introduces the sequencing framework used to operationalize the thresholds of autocratization. It then situates Hungary and Macedonia within the broader post-communist landscape, summarizes their early democratic development, and traces their decline from democratization to competitive authoritarianism. The analysis reconstructs the causal sequence from background disillusionment through critical junctures, intervening variables, and the rise of competing informal institutions as the key mechanism of autocratization. This framework ensures that the case studies contribute both to theory-driven comparison and to understanding the specific political dynamics of Hungary and Macedonia.