Cryptic crossword clue
He makes judgement that, at this time in Boston, madcap is on a hill 9

The most common and most likely answer to this crossword clue is the 9 letter word ESTIMATOR

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Buddy explains!

The cryptic/wordplay part
In cryptic crossword there's often an wordplay/cryptic part as well.
This part involves a more complex hint, such as an anagram, homophone, hidden word, etc.
Sadly, We don't have an explanation for this specific crossword clue yet.

What does ESTIMATOR mean?

ESTIMATOR noun
  1. A person who estimates, especially one who estimates costs
  2. A function of a random sample of a population used to estimate some parameter of the whole population

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