Tricky roles for one always taking second place? (5)
I believe the answer is:
loser
'one always taking second place?' is the definition.
'tricky roles' is the wordplay.
'tricky' is an anagram indicator.
'roles' is an anagram of 'LOSER'.
'for' is the link.
(Other definitions for loser that I've seen before include "Opposite of winner" , "sad type?" , "Someone who fails consistently" , "Roles for a non-winner" , "Defeated person" .)