Abstract Peace agreements can terminate organized violence without transforming the political relationships, institutions and distributions of power that sustained conflict. Existing scholarship on political settlements and peacebuilding explains important dimensions of post-conflict order, but insufficiently integrates political leadership, continuing mediation, and reconstruction as interconnected mechanisms through which settlements are reproduced or transformed. This article examined how political leadership, mediation and post-conflict reconstruction interact to reshape political settlements in Liberia and Sierra Leone. It employed a qualitative comparative case-study design, combining structured-focused comparison with process tracing to examine the trajectories from inherited settlements through leadership and political accommodation, mediation, reconstruction and institutional change. The analysis finds that peace agreements function as entry points into continuing processes of political bargaining rather than definitive settlements. Leadership shapes coalition-building and political inclusion; mediation extends beyond agreement-making into implementation and renegotiation; and reconstruction redistributes institutional authority, resources and legitimacy. The comparison shows that both cases experienced substantial but incomplete settlement transformation, with elements of inherited political power reproduced alongside institutional change. The article contributes an integrated framework linking peacebuilding, political agency, mediation and reconstruction to explain why post-conflict settlements are reproduced or transformed. The study distinguishes institutional stabilization from deeper changes in political inclusion and authority, emphasizing that durable peace alone does not demonstrate a transformed political settlement. It also identifies the limits of conclusions drawn from documentary comparison.