Commiserated with skinflint (5)
I believe the answer is:
miser
'skinflint' is the definition.
(synonyms)
'commiserated with' is the wordplay.
'with' indicates the answer is hidden within the clue.
'MISER' can be found hidden inside 'commiserated'.
(Other definitions for miser that I've seen before include "Avaricious hoarder" , "Mean-minded type" , "Penny-pinching person like Scrooge" , "Stingy type" , "Curmudgeon" .)