Both fascinating and perplexing for scholars and managers, dual executive leadership (DEL) is also challenging for the two leaders at the top level of the organization whose roles cut across professional and managerial functions and logics. Conflict may often be present in such duos and can undermine DEL success in the organization. Scholars of plural leadership suggest that trust is a key success factor for DEL relationships, although it has not been closely studied with history and context in mind. This research on DEL in eight non-profit arts organizations provides insights on how past history casts a shadow that influences trust development over time within a DEL relationship and can influence the effectiveness of leadership on the organization. Implications are drawn for research in trust and plural leadership, as well as for boards of directors and current duos in practice.