Cricketer, sympathetic about trouble (4,5)
I believe the answer is:
tail-ender
'cricketer' is the definition.
(type of cricketer)
'sympathetic about trouble' is the wordplay.
'sympathetic' becomes 'tender'.
'about' indicates putting letters inside.
'trouble' becomes 'ail' ('ail' can be a synonym of 'trouble').
'tender' enclosing 'ail' is 'TAIL-ENDER'.
(Other definitions for tail-ender that I've seen before include "Last cricketer in" , "Last man" .)