Cryptic crossword clue
Keep manager, outstanding almost to the end, in prison 9

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

I've seen this crossword clue in The Times
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Buddy explains!

The straight part
We know that "Keep manager" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case keep manager = castellan.
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 CASTELLAN mean?

CASTELLAN noun
  1. The governor or caretaker of a castle or keep.

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