Dramatist's gamble with privilege (10)
I believe the answer is:
playwright
'dramatist's' is the definition.
('playwright' can be a synonym of 'dramatist')
'gamble with privilege' is the wordplay.
'gamble' becomes 'play' (playing is a kind of gambling).
'with' becomes 'w' (abbreviation).
'privilege' becomes 'right' (I've seen this before).
'play'+'w'+'right'='PLAYWRIGHT'
(Other definitions for playwright that I've seen before include "16 dn of dramas" , "Coward, for example" , "Stoppard or Pinter, for example" , "Coward, possibly" , "Shakespeare perhaps" .)