The Philadelphia Eagles schedule for the 1998-99 season was analyzed to examine the relationship between a professional sports team and its fans. The performance of the Eagles during the season was closely monitored to determine how the team’s success or lack thereof would affect the relationship between the team and its fans. The results of this study suggest that organizations should recognize fan needs and develop strategies to maintain a positive relationship with their fans even during a losing season. Furthermore, the 2012 retirement of Philadelphia Eagles star Brian Dawkins provided an opportunity to analyze the success of a multilayered sponsorship activation. Students were asked to discuss what was successful, what was not, and what could be done for future sponsorship activations in similar situations. The case revealed that a successful sponsorship activation should be tailored to meet the needs of the target audience and provide an engaging experience. In addition, the activation should be a reflection of the brand, allowing fans to connect with the brand in a meaningful way while also communicating the brand’s message.