Bishop, experienced and fearless (4)
I believe the answer is:
bold
'fearless' is the definition.
(similar in meaning)
'bishop experienced' is the wordplay.
'bishop' becomes 'B' (abbreviation used in chess).
'experienced' becomes 'old' (associated in meaning).
'b'+'old'='BOLD'
'and' is the link.
(Other definitions for bold that I've seen before include "Valiant" , "Thick and heavy (type)" , "Confident, daring" , "Not timid" , "Intrepid" .)