A native of Hamden, Connecticut, Castiglione's first major job as a sportscaster was in Cleveland in 1979, where he called Cleveland Indians games and did sports reporting for WKYC television.
A native of Hamden, Connecticut, Castiglione graduated from Colgate University, whose sports teams are often playfully ridiculed during Red Sox broadcasts. His first major job as a sportscaster was in Cleveland in 1979, where he called Cleveland Indians games and did sports reporting for WKYC television.