This case study demonstrates the managerial conflicts and decision-making scenarios associated with corporate giving and cause-related marketing. Using the Cincinnati Bengals and their affiliation with professional football player Devon Still, we describe a series of events that led to a spontaneous nation-wide fundraising campaign to benefit pediatric cancer. The cause-related marketing (CRM) campaign raised conflicting benefits and consequences for the organization in the context of sport administration and corporate reputation. This case highlights some of the strategic and tactical dilemmas associated with CRM and corporate giving in sports marketing, public relations, and resource management. It also exemplifies the contextual facets of corporate reputation within one professional sport market.