A native of Boston, Massachusetts, Simonds graduated from Barnstable High School, and played college baseball at Davidson College as a catcher. In 1984 and 1986, he played collegiate summer baseball with the Cotuit Kettleers of the Cape Cod Baseball League, and in 1985 he played for the New Market Rebels of the Valley Baseball League. He was selected in the 7th Round of the 1987 MLB Draft by the Baltimore Orioles. Simonds played in the Orioles and Chicago Cubs organizations, reaching Triple-A.
