Five with fresh binding, broke (9)
I believe the answer is:
insolvent
'broke' is the definition.
(I've seen this in another clue)
'five with fresh binding' is the wordplay.
'five' becomes 'V' (Roman numeral).
'with fresh' becomes 'insolent' (fresh can mean rude or disrespectful. I am not sure about the 'with' bit.).
'binding' means one lot of letters goes inside another.
'v' going inside 'insolent' is 'INSOLVENT'.
Can you help me to learn more?
(Other definitions for insolvent that I've seen before include "unable to raise the wind" , "Gone bust, without a bean" , "on the rocks" , "Unable to pay debts owed" , "In the red" .)