CT is a very unique State in that it has two very different social environments. Southern CT, Hartford, New Haven and into New York is rich,big,and full of talent. The schools there get noticed. The Northeast and Northwest corners are very rural and the towns very small. My town about 7000 people.
Being from CT if I knew in what part of the State he played I may be able to provide more specific help. With the reorganization of the CIAC many smaller programs are struggling. Schools with graduating classes of 90 are playing against schools with graduating classes of 700 making it very difficult for talented small school players to get noticed. The problem seems to be that the newspapers only follow the winning programs in the middle of the state.
Because the Legions programs are boundary regulated their teams follow the same talent pool and population.
You can email me at firstname.lastname@example.org if you want to take the specifics off line.
FYI I coached at Marianapolis Prep School in NE CT.