I’m not sure it matters which school tops the Director’s Cup. All of the schools in question here have relatively strong athletics.
And why do the NESCACs have to be better than the Claremonts or vice versa? What’s wrong with just saying they’re different and exploring the ways in which that’s true? I attended a NESCAC school, as did my kids, but I’m a fan of the 5C’s. For a kid who wants the advantages of a small school while still maintaining the ability to explore academic offerings that don’t exist at the home school they sound great to me. The fact that the 5C’s are in such close physical proximity gives it an advantage over many consortia.
I have heard mixed things about the ability of kids to get the classes they want through cross-registration, but as @nostalgicwisdom’s numbers show they are taking advantage of it.