Flat broke, on the street, one starts for New York (5)
I believe the answer is:
stony
'flat broke' is the definition.
(thesaurus)
'the street one starts for new york' is the wordplay.
'one starts' indicates taking the first letters.
'for' becomes 'to' (eg both can mean 'in the opinion of').
'new york' becomes 'ny'.
The first letter of 'street' is 's'.
's'+'to'+'ny'='STONY'
'on' acts as a link.
(Other definitions for stony that I've seen before include "Cold, unfeeling" , "penniless" , "Rock-strewn" , "Rocky" , "Heartless" .)