Erie University’s star football athlete, Johnathan Snow, has led his team to an undefeated season and prospects of a conference championship and bowl game qualification. However, based on his midterm progress reports, he will be ineligible for the postseason. This case explores the challenges that the football team, the student-athlete, and the student-athlete support service department encounter when academic and athletic demands are at odds. The teaching discussion offers practical considerations for professionals in the industry or for sport management students in undergraduate or graduate courses aspiring to work in college sport.