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This appears to be origin of the phrase, which is used by someone who feels they have no chance of winning in a situation.
: "You can't win," as a catchphrase, originated in the United States and was in use by 1950 (according to Eric Partridge, "A Dictionary of Catch Phrases American and British"). It expresses a sense of futility about hoping to succeed or, generally, to get something--anything--done. 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
It just means that the person is in a no win situation.
Someone who is frustrated would say this. It basically means that every time you set out to accomplish something, you end up losing. It doesn't make sense on its surface - you are right.
Also, "I can't stand up for falling down"
catch 22 situation it's like the song "i can't stand up for falling down" lol
bad luck is constant in this person's life
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