Why are some countries wealthier than others, despite shared histories and limited resource endowments? This paper examines the economic divergence between Guinea-Bissau and Cabo Verde, two former Portuguese colonies that initially shared colonial administration and political vision through interconnected elites. Both countries were governed by the African Party for the Independence of Guinea-Bissau and Cabo Verde (PAIGC) until their political separation in 1980. Despite its comparatively rich natural resources, Guinea-Bissau remains mired in chronic political instability and underdevelopment. Cabo Verde, despite its geographical constraints and resource scarcity, has achieved remarkable stability and sustained economic development. Drawing on institutional theory and actor-centric approaches, this paper argues that post-independence governance choices and elite behaviour are the decisive factors shaping their divergent trajectories. We highlight, first, the role of institutional quality in determining economic and political outcomes, and second, the centrality of elite agency – through strategies of cooperation, competition and rent-seeking – in driving institutional divergence. Geography and natural resources alone do not determine development outcomes, nor is the colonial legacy deterministic; rather, strategic governance and institutional effectiveness are the key differentiating factors. These findings deepen our understanding of post-colonial development in sub-Saharan Africa and offer actionable insights for policy design in similarly situated small states.