Pole and German freeholder drink at dusk (9)
I believe the answer is:
sundowner
'drink at dusk' is the definition.
'sundowner' can be an answer for 'drink' (I've seen this before). I am not sure about the 'at dusk' bit.
'pole and german freeholder' is the wordplay.
'pole' becomes 's' (abbreviation for South, as in South Pole).
'and german' becomes 'und' ('and' in German).
'freeholder' becomes 'owner' (I am not sure about this - if you are sure you should believe this answer much more).
's'+'und'+'owner'='SUNDOWNER'
Can you help me to learn more?
(Other definitions for sundowner that I've seen before include "Evening drink" , "cocktail?" , "Tramp (Australian) - drink (British)" , "Victorian tramp?" , "drink after work?" .)