The NBA's current collective bargaining agreement has made maintaining continuity and loyalty increasingly difficult. The player empowerment era has further exacerbated this issue, making it harder for organizations to keep their drafted and developed players. This is evident in the case of Devin Booker, who has remained with the Phoenix Suns since 2015, a rare feat in today's NBA. The team's commitment to loyalty is further showcased by the fact that they are one of the few organizations with a player entering his 12th season with the franchise. However, the escalating salaries, annual cap growth, and restrictive tax aprons have made it challenging to afford loyalty. This is particularly evident in the conversations surrounding Devin Booker's contract, which will account for 35.1% of the cap this upcoming season. The pressure to maintain financial responsibility has led to difficult decisions, as seen in the Boston Celtics' trade of Jaylen Brown. The NBA's current system encourages organizations to move on from players who have become numbers on a cap sheet, rather than focusing on the relationships and chemistry that take years to build. This is a problem that needs to be addressed, and the author proposes a 'loyalty tax' as a potential solution. The idea is to provide cap relief for organizations that have drafted, developed, and retained homegrown players, allowing them to remain competitive while rewarding loyalty. However, the author acknowledges that there are unintended consequences and potential resistance from owners and the business side of the NBA, which may prefer constant player movement to boost merchandise sales. The current system is broken, and the NBA risks losing one of its most valuable aspects: the loyalty and relationships that make the league worth following.