This article describes efforts to develop an exploratory agent-based model as a tool for studying decision making in political regimes such as Iraq, North Korea, and Syria. Our hybrid of the landscape metaphor and the rule-based system approach captures the trade-offs leaders face in balancing components of a utility function, plus risk profiles that allow departures from conventional utility maximization. Two simple experiments concerning succession demonstrate the surprising compromises both leaders and elites are willing to make, as well as the instability of these bargains.