(one) can't win for trying(redirected from he couldn't win for trying)
(one) can't win for trying
One is unable to find or create any success, despite one's best efforts or intentions; one is constantly failing or being thwarted or spurned. Primarily heard in Ireland. That's the third manuscript to be rejected by the publishers—I can't seem to win for trying. You can't win for trying when it comes to feeding these kids. You make them what they ask for, then they say they don't like it the moment you set it down in front of them! So, first John's company goes under, and then his wife leaves him a week later? Poor fellow just can't win for trying lately.
Farlex Dictionary of Idioms. © 2015 Farlex, Inc, all rights reserved.