Charles when speaking secures wig (8)
I believe the answer is:
chastise
'speaking secures wig' is the definition.
I can't judge whether this defines the answer.
'charles' is the wordplay.
I cannot really understand how this works, but
'charles' could be 'chas' (shortened form) and 'chas' is found in the answer.
This explanation may well be incorrect...
'when' is the link.
Can you help me to learn more?
(Other definitions for chastise that I've seen before include "Inflict physical corrective treatment" , "Beat" , "Censure severely" , "Scold severely" , "Castigate or punish" .)