The paper focuses on the local delivery process of the LEADER programme over two programming periods (2007–2013 and 2014–2020). We tried to find out whether the LEADER method and projects implemented have contributed to the empowerment of the Brkini region (Slovenia), which has characteristics of a lagging and structurally weak region influenced by peripheralization processes. Quantitative and qualitative analysis of LEADER projects underlined that the Brkini region was quite successful in integrating different actors and sectors in joint projects and establishing cooperation between stakeholders. Cooperation is reflected in (1) partnerships and networking between existing and new actors and stakeholders, (2) LEADER funds being mostly used for “smaller projects” and networking within the region, (3) the synergies between LEADER and existing local aspirations as it supports several areas of the multi-sectoral approach (i.e., tourism promotion, agricultural production and processing), (4) enhanced recognisability and promotion of the Brkini region at sub-regional, regional, national and cross-border levels. In the context of empowerment, we were able to identify some incentives, but also some bottlenecks (local clubs/societies/associations lack institutional, administrative and financial capacity, etc.). Decision-makers should pay special attention to this and also promote a culture of reflexivity when preparing new animation strategies for the next programming period.