Many health care mergers and acquisitions have proven highly successful because of the geographic proximity of the institutions, coalignment strategies, complementary services, and improved financial performance. Other health care mergers and acquisitions, however, have been dismal failures. This article seeks to explain a primary cause of less successful mergers or acquisitions through the prism of a multiscale, iterative prisoner’s dilemma that occurs between department managers. Aspects of “Coping Theory,” “Resource (Conservation) Theory,” and “Social Comparison Theory” are used to analyze the experience of employees charged with making mergers or acquisitions successful. Lastly, this article suggests possible culture clash remedies drawn from the realistic conflict experiment conducted by Muzafer Sherif near Robbers Cave State Park in Oklahoma.