Cryptic crossword clue
Charlie supported by female assistant, a chum from school 9

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

I've seen this crossword clue in The Times
C
L
A
S
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M
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Buddy explains!

The straight part
We know that "a chum from school" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case a chum from school = classmate.
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 CLASSMATE mean?

CLASSMATE noun
  1. A student who is in the same class at school.
  2. (by extension) A member of a different sort of class, such as locomotives etc.

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