Encourage rascal to get rid of posh Republican flag (5,5)
I believe the answer is:
jolly roger
'flag' is the definition.
(Jolly Roger is an example)
'encourage rascal to get rid of posh republican' is the wordplay.
'encourage' becomes 'jolly' (I can't justify this - if you can you should give a lot more credence to this answer).
'rascal' becomes 'rogue' (both can mean a scoundrel).
'to get rid of' suggests deleting specific letters.
'posh' becomes 'u' (abbreviation for upper-class - opposite to non-U).
'republican' becomes 'r' (abbreviation).
'rogue' with 'u' taken away is 'roge'.
'jolly'+'roge'+'r'='JOLLY ROGER'
Can you help me to learn more?
(Other definitions for jolly roger that I've seen before include "standard not welcomed in the main" , "standard for boarders?" , "Pirate flag" , "In the main a fearful sight" , "Pirates' flag" .)