His early days on the diamond in Kalamazoo were spent honing his skills in the Eastwood, Oakwood and Westwood Little Leagues. When he started playing high school ball in 1989, his talents helped him earn a spot on the Kalamazoo Central varsity team as a freshman. Derek also spent three years playing varsity basketball, where he earned honorable mention All-State. Derek's younger sister, Sharlee, was also multitalented and played basketball, volleyball and softball, while being a member of her high school band.
After batting .557 with seven homers as a junior, Derek hit.508 (30-59) with 4 HR, 23 RBIs, 21 BB and only one strikeout in 23 games his senior year. He got on base 63.7 percent of the time and tallied an impressive .831 slugging percentage. Derek collected several awards at season's end, including the Kalamazoo Area B'nai B'rith Award for Scholar Athlete, the 1992 High School Player of the Year by the American Baseball Coaches Association, the 1992 Gatorade High School Athlete of the Year and USA Today's High School Player of the Year.
That spring, the Yankees drafted Derek with the sixth overall pick in the June 1992 draft. He was the first high school player chosen that year and became the third shortstop selected in Yankees history with a first round pick. Derek also received a scholarship to play baseball at the University of Michigan, where he would attend school in 1992 following his first summer of minor league baseball.
In 1993, his first full-year of...