Derek Jeter Won 5 World Series champion in 1996, 1998, 1999, 2000, 2009. Jeter was drafted by New York Yankees in 1992 and debuted in the major leagues in 1995. He spend his entire 20-year MLB career with the New York Yankees from 1995 to 2014. He was awarded World Series MVP in 2000. His accolades include 14 All-Star selections, five Gold Glove Awards, five Silver Slugger Awards, two Hank Aaron Awards, and a Roberto Clemente Award.