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This article explores two most-different cases – South Africa and Benin – with highly diverse challenges, extremely varied party systems, and yet strikingly similar pathways to establish and maintain democracy against all odds in the decades following democratization. In both countries, extreme political, economic, and ideological crises made incumbent parties concede to reforms. These concessions resulted in a bargain with rising opposition elites for security and future political inclusion. In these cases, opposition elites realized significant benefits to stability and order that could be had with including the old regime in the new ruling coalition. Despite the challenges of a racially or ethnically cleaved society in South Africa and Benin, the democratic bargain was maintained through self-interested and embattled incumbents staring down the precipice and opting for institutional compromise given the infeasibility of maintaining the status quo and opposition elites’ preferences for maintaining economic and social order that they could inherit when allowing the incumbent some enduring role. Yet after 30 years, democratic backsliding is a consequence of a new political elite class centralizing power in the wake of this reordering, once the imperative for inclusive bargains and stability had diminished following the successful transition.