Definition of I or he, she, etc. can't win in English:
informal There is no course of action will bring success or please people.
- Second, you can't win with an irrational critic like Bowers.
- We know how difficult it is, but you only make it harder for yourself if you go down with the attitude that you can't win.
- In this kind of ethical dilemma you can't win; damned if you do, damned if you don't.