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  1. 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.

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  3. When one says “I can’t win for losing,” they mean “I can’t win because I’m losing all the time.”. The confusing part of the phrase is the use of the preposition for to mean ‘because of,’ a sense primarily found in idioms such as this one. Do not search for deeper meaning. There is none. It is usually used after a series of ...

  4. Jun 19, 2022 · What does Can’t Win for Losing mean? Can’t win for losing refers a popular United States-based colloquialism, used for expressing a series of bad luck and a lack of success. A good example for a situation, which may invoke the feeling is a Pay to Win videogame, where a user truly “Can’t win for losing” resulting in a lack of Winner ...

  5. Mar 19, 2002 · The elaboration "You can't win for losing," with its added play on logic, was around in the 1960s. It means that losing keeps you from winning; you can't win because things keep going wrong. People would say it when something unexpected or a bit of bad luck spoiled their plans. Actually, the word 'for' may be taken out of context here.

  6. Jan 28, 2015 · The authors, Barbara Ann Kipfer and Robert L. Chapman, give this example: “We busted our humps, but we just couldn’t win for losing.”. Kipfer and Chapman date the expression from the 1970s, but we’ve found earlier examples in Internet searches. The earliest is from a 1955 issue of the Postal Supervisor, a journal of the National ...

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