He may want to change roles with the winner (5)
I believe the answer is:
loser
'he may want' is the definition.
The answer is a person as well as being a singular noun. This is suggested by the definition.
'change roles with the winner' is the wordplay.
'roles' anagrams to 'LOSER'.
Though, I am not clear how the anagram is indicated.
'to' acts as a link.
Can you help me to learn more?
(Other definitions for loser that I've seen before include "Defeated competitor" , "one that's been left behind" , "Unsuccessful competitor" , "Defeated contestant" , "lemon" .)