Cryptic crossword clue
Retired councillor – a non-gambler – keeps having repeated wins 2,1,4

The most common and most likely answer to this crossword clue is the 2 plus 1 plus 4 letter word ON A ROLL

I've seen this crossword clue in Independent
O
N
A
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Buddy explains!

The straight part
We know that "keeps having repeated wins" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case keeps having repeated wins = on a roll.
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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