Crossword Genius

The foolishness of backing some filly (5)

Ross

I believe the answer is:

folly

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'the foolishness' is the definition.
('folly' can be a synonym of 'foolishness')

'of backing some filly' is the wordplay.
'backing' suggests the final letters.
'some filly' becomes 'olly' (I can't explain this - if you can you should believe this answer much more).
The final letter of 'of' is 'f'.
'f'+'olly'='FOLLY'

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(Other definitions for folly that I've seen before include "Absurdity" , "'Where ignorance is bliss. 'tis . . . . . to be wise'" , "mock Gothic building" , "'Madness, stupidity (5)'" , "Foolishness" .)

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