Not Win For Losing Meaning

(idiomatic, US) To repeatedly fail in one's gambles or efforts.

Example: 1910, Hartley Withers, The Meaning of Money, page 42
  Figure 1 depicts a number of these forces, and suggests the ways in which the Individualistic Ethic "could not win for losing."
1936, Reuben Davis, Butcher Bird, page 14
  Manboy grinned, and looked up as Two-Way joined them, laughing. "Gabe you is just naturally a Jonah to your own self, and can't win for losing no matter what.