Cryptic crossword clue
Winston, when intimate and divested of habit, just not managing it 5,3,2,5

The most common and most likely answer to this crossword clue is the 5 plus 3 plus 2 plus 5 letter word CLOSE BUT NO CIGAR

C
L
O
S
E
B
U
T
N
O
C
I
G
A
R


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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.


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