Plundered Toledo, sadly (6)
I believe the answer is:
looted
'plundered' is the definition.
('loot' can be a synonym of 'plunder')
'toledo sadly' is the wordplay.
'sadly' is an anagram indicator.
'toledo' anagrammed gives 'LOOTED'.
(Other definitions for looted that I've seen before include "Plundered and robbed" , "having taken part in a robbery" , "Ransacked, plundered" , "Sacked" , "Plundered, pillaged" .)