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This study sheds light on the current patterns of punishing behavior. Experimental work with ultimatum bargaining shows that individuals have a high sensitivity to fairness, and when taken advantage of, are willing to endure costs to punish deviant behavior. Third party observers of the unfair behavior asked to represent ultimatum recipients are more hesitant to engage in such punishment. This becomes ever more puzzling when we consider individuals’ high value of their own reputation in similar settings. This leaves both rational choice modelers and political psychologists puzzled. This study presents the baseline model for a research agenda proposing a multi-agent modeling approach that allows for analysis of the observed behavior’s adaptiveness from an evolutionary perspective. Understanding discrepancies between individual and representative third party behavior is crucial for understanding issues of political representation.