My problem with this question is it is usually only judged in hindsight, where high school greatness is measured by pro career accolades (and to a lesser extent college accolades). How good you were in high school doesn't totally correlate with how good you will be as a pro and vice versa.2004 High School class for example
had our old buddies Sebastian Telfair, Robert Swift, and Glenn Davis at #6, #8, and #11 in that class. Ahead of Rondo (#21), Lowry (#29), Horford (#47), Noah (#72). So if you put Telfair/Swift/Davis and a couple other scrubs from the top 20 on one team against Rondo and Co., and asked that question when they were all still in high school, everybody would probably vote 100% Telfair's team was the better team hands down, ask that question now, everybody would think Rondo's team was the better one.
Even if the question is re-worded, who has the best collection of future NBA talent or something, still probably comes down to Oak Hill or Dunbar (of course we'll only be able to judge this sometime in the future).
The question is still interesting though, so trying to find a somewhat unbiased evaluater, I went with McDonald's All-Americans (because it's well known and data was easy to find).
Weston did have 2 McDonald's All-Americans with Bamba ('17) and Reddish ('18), but that's not even that unique, Oak Hill had 2 in '18 and 1 in '17, and an Indiana school had 2 in '17 (one of them being Jaren Jackson Jr).
Altogether, since 1977 these are the standouts:
Oak Hill Academy (Mouth of Wilson, VA) -27
DeMatha Catholic (Hyattsville, MD) -12
Paul Laurence Dunbar (Baltimore, MD) - 7
Saint Anthony's (Jersey City, NJ) - 7
Findlay College Prep (Henderson, NV) - 7
Roman Catholic (Philadelphia, PA) - 6
Mater Dei (Santa Ana, CA) - 6
With 125 other schools having between 2 and 5.
Oak Hill had a 7 year stretch ('90-'96) where they had 1, 2, 2, 2, 1, 1, 1 in consecutive years (including Stackhouse, Stephen Jackson, Ron Mercer). Now Oak Hill is unique in that most kids don't attend that school for 4 straight years and might only transfer for their Senior year, so who knows how many of the kids from different years actually played together, but without actually looking up those rosters and their records, I'm guessing the list of best high school teams of all time, you'll see Oak Hill like you see Wilt's name in the NBA record books.