The most common and most likely answer to this crossword clue is the 7 letter word DICIEST
I've seen this crossword clue in The Times
D
I
C
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E
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T
More clues leading to the result DICIEST
Buddy explains!

The straight part
We know that "least likely to succeed?" is the straight/definition part of the clue. The straight part is often a synonym or definition, in this case least likely to succeed? = diciest.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 DICIEST mean?
DICIEST adjective- Fraught with danger.
- Of uncertain, risky outcome.
- Of doubtful or uncertain efficacy, provenance, etc.; dodgy.
- Nauseating, rank.