Cryptic crossword clue
Bookish boss with evidence of debts 8

The most common and most likely answer to this crossword clue is the 8 letter word STUDIOUS

I've seen this crossword clue in The Times
S
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U
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S


Buddy explains!

The straight part
We know that "Bookish" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case bookish = studious.
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 STUDIOUS mean?

STUDIOUS adjective
  1. Given to thought, or to the examination of subjects by contemplation; contemplative.
  2. Dedicated to study; devoted to the acquisition of knowledge from books
  3. (usually followed by an infinitive or by "of") Earnest in endeavors; attentive; diligent
  4. Planned with study; deliberate; studied.
  5. Favorable to study; suitable for thought and contemplation

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