Typical helper on expedition, one carrying the flag? (8-6)
I believe the answer is:
standard-bearer
'typical helper' is the definition.
The answer and definition can be both people as well as being singular nouns.
Maybe there's an association between them I don't understand?
'on expedition one carrying the flag?' is the wordplay.
'on expedition' becomes 'bearer' (I can't explain this - if you can you should give a lot more credence to this answer).
'one carrying' is a charade indicator (letters next to each other) (in a down clue, the bottom letters carry others).
'the flag?' becomes 'standard' (standard is a kind of flag).
'bearer' after 'standard' is 'STANDARD-BEARER'.
Can you help me to learn more?
(Other definitions for standard-bearer that I've seen before include "Flag-carrying soldier" , "Leading figure in a cause" , "Leader of a cause" , "Leading figure in a movement" .)