The political faction Chuck is with? (5)
I believe the answer is:
lobby
'the political faction' is the definition.
'lobby' can be an answer for 'faction' (thesaurus). I'm unsure of the 'the political' bit.
'chuck is with?' is the wordplay.
'chuck' becomes 'lob' (I've seen this before).
'is with?' becomes 'by' (I am not sure about this - if you are sure you should believe this answer much more).
'lob'+'by'='LOBBY'
Can you help me to learn more?
(Other definitions for lobby that I've seen before include "Entrance hall - seek to influence" , "Shy" , "Hallway; seek to influence" , "Attempt to influence" , "Small hall" .)