Donald Mattingly was born on April 20, 1961 in Evansville, Indiana. He graduated from Reitz Memorial High School in 1979, but instead of going to college, Don was drafted in the 19th round of the amateur draft in 1979 by the New York Yankees. He made his major league debut in 1982.

During the end of the 1983 season, Don played between first base and the outfield, waiting for a full time position to open up. In 1984, he finally got a full time position on first base, which is the position he played until he retired in 1995. Mattingly was nicknamed “Donnie Baseball” and “The Hitman,” becoming one of the most popular players on the Yankees. In 1985, the lefty won the MVP in the American League. His stats for that year were impressive; he batted .324 and had 35 home runs, 48 doubles, and 145 RBIs (the most in a season by a left-handed batter since Ted Williams in 1949). Suffering from back problems in 1990, Mattingly's game was declining. In his 13 seasons with the New York Yankees, they never made it to a playoff game. In 1995, the team finally made a playoff game on a wild card, but unfortunately lost to the Seattle Mariners in the 11th inning of game five.

Mattingly retired in 1995, and in 1997 he started work at the Yankees' spring training camp in Tampa Florida as a special instructor, where he stayed for seven seasons. In 2003, he started work as a hitting coach, and in 2006, he was promoted to being bench coach to Joe Torre. Mattingly thought that he was the front runner for the position of manager, but he did not get the job and left the Yankees in 2007 to become the hitting coach for the Los Angeles Dodgers.