Effective coaches must understand and manage athletes’ expressions of disagreement or dissatisfaction. The current study identified the triggering events that athletes reported as the impetus for their dissent, the messages that they utilized when dissenting, and the success of these messages. Four categories of triggers were identified within data collected from 262 former high school athletes: (a) performance issues, (b) power and influence, (c) logistics, and (d) communicative climate and culture. These triggers were associated with athletes’ subsequent expressions of dissent. Athletes most commonly utilized solution presentation and direct-factual appeals when dissenting about these triggers. Athletes’ dissent messages predicted the success of their dissent; effective expressions more readily featured solution presentation messages, direct-factual appeals, and an absence of humor. Appropriate expressions were predicted by the use of solution presentation messages and the avoidance of pressure, circumvention, and humor. Collectively, this research highlights features unique to the sports team context, including team interdependence, the balancing of the multiple roles that come with being a student-athlete, and cultures of rationalism and respect for authority and sporting norms.