Starting his career in the 1965 season, Gregory was not an official member of the Fairfield County Football Officials Association member. He officiated the Danbury High JV and Freshman games with Matt Johnson and Alan Meath as his apprentice masters. He passed the FCFOA exam in 1966 on a Tuesday and my first game for that association was a varsity prep school game the following Saturday. Three years later he became the referee of my own crew. He was Secretary/Treasurer of the FCFOA for 11 years and was the first unpaid JV/Freshman football commissioner for the WCC (Western Connecticut Conference) schools. "I did this because no one wanted to come up to the Danbury area to work sub-varsity games " he states.. I did this for about 7 years. His crew worked the first WCC Championship game that used the Kansas tie game procedure (Masuk vs. New Fairfield) three (3) FCIAC Championship games. He has one state game to his credit. He became a founding member of the Colonial Football Officials Association and is now an honorary member of both the FCFOA and CFOA The Colonial Board has named its Sportsmanship Award in his name, which is given to the team in the South West Conference that has demonstrated the best team sportsmanship for the year. His officiating career ended in 1987. My last game was at New Fairfield High School "on perhaps the coldest day of my 21-year career".