With over $3.5 billion to divide between roughly 1,200 players each year, the Major League Baseball Players Association (MLBPA) is described by members and scholars as the most powerful union in the country. When the then-ineffective MLBPA was founded in 1953, private sector unionization was at its zenith. Today, the MLBPA is at the height of its power at a time when private sector unionization has hit a nadir. Considering this, it can be tempting to regard the MLBPA as a formidable outlier that has successfully bucked the trend of deunionization. However, the reality is far less uplifting. To achieve success, the MLBPA has actually repressed low-level workers within the same industry, thereby creating a microcosm of our current era — the New Gilded Age, defined by a growing divide between rich and poor — in professional baseball. This repression has come in the form of restricting minor league player rights and is exemplified by the union’s actions during the 1994-1995 player strike, the rollback of baseball’s antitrust exemption, and changes to the format of the amateur draft. This shift from policies that benefit the largest number of players to ones that favor superstars has resulted in rampant individualism within the baseball world and has perhaps been to the detriment of the union’s well-being. This work illustrates how a large concentration of labor power shared only by a few select workers within an industry can be just as problematic for lower level worker rights as a large concentration of corporate power.