What Does Can’t Win for Losing Mean?

Can’t Win for Losing Meaning

Definition: You can’t win because you keep losing; things would be going great if they weren’t going so poorly.

People use this phrase when problems keep occurring that stop them from winning or accomplishing their goal.

Origin of Can’t Win for Losing

This expression become popular around the 1960s, but may have existed before then.

It comes from the literal meaning, which is that losing over and over again prevents a person from winning.

The main idea is that a string of bad luck or misfortune has beset someone and this keeps him or her from succeeding. This person may try and try, but every time he or she does, they get bested by someone else or manage to fail somehow. Despite their best attempts, they still manage to lose. In other words, they can’t win for losing.

Examples of Can’t Win for Losing

you cant win for losingIn this dialogue, a brother and sister are discussing the chess games they’ve been playing.

Maria: I win again. How many games has it been now?

Franco: Ugh! I don’t know. That’s like fifteen games in a row. I don’t know what’s wrong with me.

Maria: I think it’s just mental. You’ve lost so many times now that you are starting to believe you can’t win. You’re not a bad player.

Franco: You’re right. I can’t win for losing.

Maria: Do you want to try again?

Franco: Maybe tomorrow. I’m going to give myself a pep talk.

I cannot win for losingThe second example shows two university students who are complaining about a professor.

Lorenzo: I don’t know why that professor hates me.

Alba: Yeah, it does seem like he dislikes you.

Lorenzo: Every time I try to say something nice, or something neutral, he interprets it the wrong way and gets offended. It doesn’t matter what I try to do to make him like me; it never works.

Alba: Like what? What did you say that was nice but offended him?

Lorenzo: For example, the other day I told him I liked his new haircut, and he accused me of hating his old haircut!

Alba: Yikes! You just can’t win for losing.

Lorenzo: That’s for sure.

More Examples

The excerpt below uses the expression to refer to a poorly performing hockey team.

  • As coach of the Avalanche, he’s stuck with the worst job in the NHL. So what’s the only upside to being Jared Bednar, enduring the pain of a franchise that can’t win for losing? He’s as invisible as a ghost in Denver. –Denver Post

This excerpt uses the expression to refer to two unpopular candidates for president.

  • What it says is that we’re in big trouble either way. This election gives a whole new lack of meaning to “Can’t win for losing.” That would be the voters. –New York Daily News


The idiom can’t win for losing is another way to say one’s constant losses are preventing wins.