A native of Enfield, Connecticut, Whalen attended Enrico Fermi High School. As a senior, he was the State Class "LL" Heavyweight Wrestling Champion and placed 3rd at the State Open Championships. For football Whalen was All-CCIL on both offense and defense and an All-State honorable mention. He took a postgraduate year at Loomis Chaffee, where he was the New England Prep Champion and 3rd in the National Prep Wrestling Championships while being named 1st team All-Prep and All-State in football. Whalen would go on to attend Wesleyan University in Middletown, Connecticut. He was a four-year starter as an offensive lineman for the Wesleyan Cardinals football team before receiving his degree in 1983. He was also the captain of the wrestling team at Wesleyan, earning All-New England and All-Amer