It’s hard to pinpoint just what has kept the White Sox from building sustained success, despite an overall good player development model.
Think about it. Even when Chicago has been at its worst since catching fire en route to winning the World Series in 2005, they’ve still managed to have exciting young players. For example, though they lost 99 games in 2013, Chris Sale continued to break out as a starter. 2018 was a 100-loss season, but star shortstop Tim Anderson kept blossoming.
Long story short, the reasons the White Sox have continually underperformed could probably fill a volume of Baseball America.