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Economists guided by evolutionary psychology have theorized that in an iterated Prisoner’s Dilemma reciprocal behavior is a product of evolutionary design, where individuals are guided by an innate sense of fairness for equal outcomes. Empathy as a pro-social emotion could be a key to understanding the psychological underpinnings of why and who tends to cooperate in a collective act. In short, why are some individuals more prone to participate in collective-action? The hypothesis that a pro-social psychological disposition stemming from self-reported empathy will lead to grouporiented behavior in an iterated Prisoner’s Dilemma game is tested. Results suggest that an empathetic disposition does not lead to a higher rate of cooperation, but interacts with environmental conditioning to produce either a highly cooperative or highly uncooperative personality type.