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Doubt Milford was ahead of Hotchkiss or a few other big schools. You can usually tell which school was a feeder for what by school colors.
The linkage between the current and the old Milford is sketchy at best. Different campus, different mission and purpose. It kills me when Milford is compared to real schools even like Worcester Academy or Cheshire. Not that Milford is some awful place, but it's a different animal altogether.
Trevardo went to Canterbury in New Milford. It's a very good and legitimate Academic institution. When a kid goes to a place like Canterbury, Salisbury, Hotchkiss, Avon Old Farms etc.. the student is a student. Sports is secondary. I went to Salisbury and there was always a Postgraduate (PG) or two that would show up in the senior class. Most of them were hockey players doing a PG year because West Point wanted them to. But most of those guys had a great experience at a school that gave them intensive academic guidance.
Just about every major private school had students like this. Choate, AOF, Hotchkiss, Salisbury etc. South Kent is a very small but legit school that has made a niche. In most cases these schools are small and they only will accept a student that is serious.
So when a kid goes to one of the "real" schools, then I get much more of a warm fuzzy than with Milford. But Milford no doubt has a decent track record in matriculating students to where they want to be.
FWIW: Deon Anderson went to Avon. I love the guy, one of the best football players ever to come out of UCONN, IMO - but let's be real now.