An American CEO who had built a large, highly successful national business faced a hard decision. He had the opportunity to become the main cleaning contractor for the Washington Redskins football team. However, he had concerned about working with a company whose name and logo offended him, some of his employees, and some number of Americans. Yet it promised to be a lucrative opportunity that would open the door to even more. This (disguised) case is designed to surface and explore students' instinctive decision-making tendencies around a high-stakes leadership situation. Thus, it is short enough to be read and responded to in class. Students are assigned readings and assignments related to the case after class discussion in which they are encouraged to further reflect on their initial responses. This case can be used to focus on the decision itself—take the contract or not—or on how the decision should be made (i.e., on the decision-making process). The case is quite flexible and would work in any course that deals with leadership, ethics, decision-making, organizational behavior, human resources, and related topics. It is appropriate for a range of levels and audiences, including undergraduate, MBA, and executive education.