This paper proposes a novel approach to study legal interactions. In particular, we focus on cases of medical liability and investigate the mechanisms governing legal litigations in different judicial environments. To do that, we use an agent-based model where lawyers are explicitly and individually represented in the model. Lawyers in the model are heterogeneous in the sense that they may follow different argumentation strategies to try to win the cases of medical liability they are assigned. They may also change their strategy if they observe that other strategies work better in the particular context they are embedded. In this way, our agent-based model offers a complementary approach to understanding legal interactions within an evolutionary framework. More concretely, we explore how various factors, such as the magnitude of legal expenses and the accuracy of the judicial system, affect the type of litigation strategies that are successful and prevail in a certain judicial context.