This case study examines a U.S. History class where a veteran teacher uses challenging primary source documents and a debate to encourage his students to think critically about history. The teacher is knowledgeable about the subject matter and articulates a clear purpose for teaching. Surprisingly, the author finds that the teacher's methods, which include the use of competitions and games, contradict some of his espoused teaching goals and some student's engagement in the class. The ambitious four-week competitive debate the teacher enacts creates an adversarial classroom climate where students focus on competing with each other. Additionally, the teacher's jokes and sense of humor encourage students' attention during lessons, but limit student's abilities to discuss issues intelligently. The findings add to the research base about teachers who use entertainment and gamesmanship, and illustrate how a teacher's beliefs and pedagogy undermined the quality of lessons and the student experiences in the class.