Since the rise of players' unions helped equalize the bargaining power between players and team owners in professional sports, sports leagues have struggled to find economic regulatory systems that satisfy both sides. Many mechanisms have been employed; the most recent such device is the "luxury tax." Current versions of the luxury tax-utilized by Major League Baseball and the National Basketball Association (NBA)-require that teams with aggregate player salary expenditures above a specified level are assessed a tax. This Note focuses primarily on the robust taxation system employed by the NBA because it is likely to be used as a viable model for other leagues. When examining the NBA taxation model, however, it becomes apparent that it has serious imperfections and, in fact, works against its stated goals. This Note uncovers the various consequences of the NBA luxury tax and offers some solutions to its structural flaws.