This case was prepared by the author for the Diamond Dollars Case Competition in March 2013. It was developed for the purpose of a case discussion. It contains various assumptions that were generated for illustrative purposes and is not intended to serve as a source of primary data. It takes the hypothetical 2013 performance of young baseball superstar Mike Trout to provide students with an opportunity to apply analytical skills to the types of real-world problems faced by professional sport organizations. The case study invites students to weigh the many factors that Los Angeles Angels management must consider in determining how to realistically negotiate with Trout for the benefit of the ball club following the 2013 Major League baseball season.