The New York Yankees' front office and top decision makers have been a major part of the team's problem dating back to 2002. Since then, the Yanks have three World Series appearances and just one title. They got too high off of the late-90s supply, it would seem.
Brian Cashman, while a top executive, has his hands all over problematic personnel moves. But perhaps the bigger issue is the crew he surrounds himself with. It's all very outdated, and few changes have been made over the last two decades, despite the same shortcomings.
What are those shortcomings?