For most of his career, Sheffield played right field, though he has also played left field, third base, shortstop, and a handful of games at first base. He played for the Milwaukee Brewers, San Diego Padres, Florida Marlins, Los Angeles Dodgers, Atlanta Braves, New York Yankees, Detroit Tigers, and the New York Mets. Sheffield was a first-round pick of the Brewers, who selected him sixth overall in the amateur draft after a standout prep career at Hillsborough High School in Tampa, Florida. He bats and throws right-handed.