Bother an educator and an iconic rebel (8)
I believe the answer is:
headache
'bother' is the definition.
(thesaurus)
'an educator and an iconic rebel' is the wordplay.
'an educator' becomes 'head' (head is a kind of educator).
'and' is a charade indicator (letters next to each other).
'an' becomes 'a'.
'iconic rebel' becomes 'Che' (revolutionary Che Guevara).
'head'+'a'+'che'='HEADACHE'
(Other definitions for headache that I've seen before include "big problem" , "trial" , "Worry, trouble (colloq.)" , "A pain in the brain" , "Source of worry (and pain!)" .)