Many 2004 presidential-election campaign advertisements were strategically targeted to appeal to viewers of sporting event telecasts. The Bush–Cheney campaign’s unauthorized use of the term Olympic in advertisements that aired throughout the 2004 Summer Olympic Games telecasts raised novel legal issues at the intersection of trademark law and constitutionally protected political speech. This article provides an analysis of the legal issues surrounding the Bush–Cheney campaign’s unauthorized use of the term Olympic. This article first examines the viability of trademark, unfair competition, and misappropriation-based claims potentially available to the United States Olympic Committee and other sport organizations. The article then examines some state-based regulations and case law regarding false and deceptive political campaign advertising that suggests a possible legal challenge to future political advertising campaigns that use sport organization trademarks without authorization. In addition to providing implications for sport managers, this article suggests that Congress may need to revisit latitudes afforded political speech to prevent a dangerous trend of political candidates’ misrepresenting their association with sport organizations.