Derek Jeter only knew one thing for the last twenty years, and that was playing shortstop and being the leader of the New York Yankees. So when he announced his retirement plans prior to the 2014 season, not only was the sports world shocked, many wondered how he would be able to move on from the game he had become accustomed to playing. Derek's life was a set schedule and now he would have to wake up every morning not knowing what his next venture would be. Yes he always expressed interest in one day owning a team, but how would that really fill the void of no longer playing in America's favorite pastime?
