The most common and most likely answer to this crossword clue is the 5 plus 3 letter word CIGAR BOX
I've seen this crossword clue in The Guardian
C
I
G
A
R
B
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X
Buddy explains!
The straight part
We know that "would one often open for Churchill?" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case would one often open for churchill? = cigar box.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.