Deceive gangster and win a thousand (8)
I believe the answer is:
hoodwink
'deceive' is the definition.
(hoodwinking is a kind of deceiving)
'gangster and win a thousand' is the wordplay.
'gangster' becomes 'hood' (I've seen this before).
'and' means one lot of letters go next to another.
'a thousand' becomes 'k' ('K' can be a synonym of 'thousand').
'hood'+'win'+'k'='HOODWINK'
(Other definitions for hoodwink that I've seen before include "Delude" , "Put wool over eyes of" , "Deceive, trick" , "Deceive, fool" , "Dupe, bamboozle" .)