Anderson had brief cameos with the Boston Red Sox in 1988 and the Cleveland Indians in 2002, although his career is bookended by a brief early spell with the Boston Red Sox and a last year in MLB as a Cleveland Indian. He was drafted by the Red Sox in the 1st round (11th pick) of the 1986 amateur draft. He spent most of his time with the Red Sox playing second base and third base, but also saw some time at first base and the outfield. In 1989 he started 69 games at second base and hit.275 with 14 homers and 78 RBI's. In 1990 he started only 48 games because of an ankle injury, but still hit.273 with 11 homers and 49 RBI's. His career high in hits was 150 in 1991 while his best season overall was probably in 1992 when he played in 79 games and had 91 RBI's. After that disappointing season he was traded to the Indians for Jeff Reardon. The Indians were looking for someone to replace Omar Moreno who had just been dealt to the San Diego Padres. They thought they had found that player in Anderson who had been very successful before losing most of his games due to injuries. Unfortunately for Anderson, he never recovered from those injuries and ended up spending one more season in Cleveland before retiring after the 1994 season.