Possible Clues:

• See 143-Down
• For this there's no W in it
• There's no W in it for one
• It's said John's a failure
• There's no W in it for him
• No-hoper could be changing roles
• No W in one that's not one, by the sound of it (5)
• Beck song with the lyric "Soy un perdedor"
• Terse putdown
• One not winning