The article presents the historical development of the Kočevje region in light of political experimentation from the Second World War to present day. The core of the empirical study is the period between 1991 and 2021, when the Kočevje region confronted economic decline and social turmoil, which were a consequence of past political decisions. We studied the available literature and statistical data and conducted ten interviews with key local stakeholders, based on which we then identified three periods of the contemporary development of the Kočevje region. The post-independence transition (1991–2010) marked the destruction of industrial companies, the non-responsiveness of the local environment, and the overall stagnation in development. The establishment of new local government (after 2010) brought about a developmental shift, the economic revival, and a change in mentality. The current period (after 2016), on the other hand, represents the arrival of an established international company and an improvement in the external image of the Kočevje region.