Sherman graduated from Lynwood High School in California and began his college baseball career at Cerritos College. The team had a record of 84–11 in his two years at the school. In 1988, he set school records in runs scored, walks, times on base and stolen bases. Sherman chose to continue his college baseball career at Long Beach State after reneging on a commitment to play at Cal State Fullerton. In 1989, Sherman helped lead the Dirtbags to the College World Series.
Sherman was selected by the San Diego Padres in the sixth round of the 1989 Major League Baseball draft. In December 1991, Sherman was selected by the Baltimore Orioles in the Rule 5 draft. Sherman was expected to compete for Baltimore's leadoff spot or a fifth outfielder role but was ultimately returned to the Padres before the start of the 1992 season.
Sherman spent the subsequent year in the minors and was promoted to San Diego's 40-man roster for the first time in the November following the 1992 season.

Return to Darrell Sherman Autograph Profile