Gary Antonian Sheffield was born on November 18, 1996, in Tampa, Florida. Sheffield was always considered a big talent as he was selected with the 6th pick of the 1986 MLB Draft by the Milwaukee Brewers.
After two quick years in the minors, Leagues Sheffield made his major league debut on September 3, 1988 against the Detroit Tigers when he was still a teenager. That was the beginning of a 4-season tenure on the Brewers during which time he played shortstop and third base, not quite living up to the hype. Sheffield played an average of only 90 games per season from 1989-1991.