This chapter provides an overview of the key concepts underlying informed decision-making, with illustrations from ten decision contexts faced by the San Francisco Giants of Major League Baseball. These decision contexts have greatly shaped the path that the Giants have traveled over multiple decades. Decision-making in the sporting world often happens in a fishbowl, with many from the outside making public judgments, often with very limited information, and with hidden or not-so-hidden agendas. Uncertainty is a central aspect of decision-making. Consider negotiations between the general manager of a club and a potential player that is a “free agent” who is available to join the club for the coming season. Sporting clubs make multiple player contract decisions each year. Important learnings can be gained by a structured analysis of both contracts that have good outcomes and those that have bad outcomes.