In this case, we explore the ethical and reputational impacts of the NFL’s partnership with online sports betting sites like FanDuel and DraftKings. Through cross-promotional activities, a deep investment in the promotion of fantasy football, and an intentional blurring of the lines between sporting events and wagering on those events, the NFL has gone all-in on its connection with online gambling, but at what cost? Can the NFL ignore the growing body of research on the addictive nature of online gambling, particularly among its core demographic groups? Do the partnerships between the NFL and online gaming sites have the potential to alienate the NFL from future viewers? Are the rewards of these affiliations worth the reputational risk to one of the most recognized brands in the world? What responsibility does one partner have for the consequences of the other partner’s practices and the outcomes of those practices?