not win for losing

Meaning: (idiomatic,US)To repeatedly fail in one'sgamblesor efforts.1910, Hartley Withers,The Meaning of Money, page42:Figure 1 depicts a number of these forces, and suggests the ways in which the Individualistic Ethic "couldnot win for losing."1936, Reuben Davis,Butcher Bird, page14:Manboy grinned, and looked up as Two-Way joined them, laughing. "Gabe, you is just naturally a Jonah to your own self, andcan't win for losingno matter what.

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