Wining Boy is described as being exploitative and selfish even before he comes on stage in this play. This is not necessarily a negative trait, but it is Wining Boy's nature to "play the angles" or cheat.
Some examples of the ways he can be said to exploit people are seen in the action of the play:
- Wining Boy asks Doaker for a drink despite the fact that he did not offer to share any of his own whiskey with Doaker.
- Wining Boy sells Lymon his suit for a fair price, but then convinces Lymon also to buy a pair of shoes from him.
More evidence of Wining Boys tendency to scheme or cheat people comes in the stories we hear about him, including those he tells himself:
- Wining Boy cheats on his wife though he loves her.
- Wining Boy is described as a card sharp on several occasions, and Boy Willie tells Lymon not to play cards with him or Wining Boy would take all of his money.