A captain in a winning position (5)
I believe the answer is:
ahead
'in a winning position' is the definition.
'a captain' is the wordplay.
'captain' becomes 'head' (both can mean a leader).
'a'+'head'='AHEAD'
(Other definitions for ahead that I've seen before include "In the lead, in advance" , "What's down the road" , "In the vanguard" , "at pole" , "Forwards" .)