Penniless, poor (5)
I believe the answer is:
needy
This clue is a double definition.
'penniless' is the first definition.
(I've seen this before)
'poor' is the second definition.
(I know that needy is a type of poor)
(Other definitions for needy that I've seen before include "Penurious" , "Poverty-stricken" , "Poor; wanting affection" , "Hard up" , "penniless" .)