Posted by R. Berg on March 19, 2002
In Reply to: Phrase Help posted by CRB on March 19, 2002
: I need help with the meaning and origin of the phrase "can't win for loosing."
"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. People would say it when something unexpected or a bit of bad luck spoiled their plans.