(one) can't win for losing(redirected from you can't win for losing)
(one) can't win for losing
One is unable to find or create any success; one has been constantly and/or thoroughly defeated, bested, belittled, etc., in recent times. So Mary divorced John after their company went under, and then his mother died a week later? Man, that guy can't win for losing lately. That's the third manuscript to be rejected by the publishers; I guess I just can't win for losing.