Following defeat over money, a character displays clever quality (9)

'quality' is the definition.
(nattiness is a kind of quality)

'following defeat over money a character displays clever' is the wordplay.
I cannot really understand how this works, but
'money' could be 'tin' (old-fashioned slang term for money) and 'tin' is present in the answer.
'a' is found in the answer.
'character' could be 'ess' (the letter S) and 'ess' is found within the answer.
This explanation may well be incorrect...

Can you help me to learn more?