Winning man promises to pay (10)
I believe the answer is:
victorious
'winning' is the definition.
(I've seen this before)
'man promises to pay' is the wordplay.
'man' becomes 'victor' (**).
'promises to pay' becomes 'ious' (more than one iou).
'victor'+'ious'='VICTORIOUS'
(Other definitions for victorious that I've seen before include "winning" , "Triumphant" .)
I've seen this clue in The Telegraph.
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