Huskey was expected to have a limited bench role with Seattle, but his bat (15 home runs in only 262 at-bats) earned him more and more playing time. While Seattle had no playoff hopes at midseason, several other teams still did, and were looking to bolster their rosters. One such team was the Boston Red Sox, who acquired Huskey on July 26, 1999, in exchange for Robert Ramsay. Huskey served as a right-handed complement to Boston's left-handed designated hitter, Brian Daubach. Huskey performed well in Boston, hitting seven home runs down in the second half of the season in only 124 at-bats and helped the Red Sox to a wild card berth. Following the season, Huskey signed a one-year contract with the Minnesota Twins on January 27, 2000.