Q: Is the expression “You can’t win for losing” as simple as it sounds? Or is there a deeper meaning and significance?
A: We don’t see anything particularly deep about the expression. It’s just another way of saying “You can’t win if you’re losing all the time.”
The Dictionary of American Slang (4th ed.) says the usage refers to someone “entirely unable to make any sort of success” or “persistently and distressingly bested.”
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 Association of Postal Supervisors:
“You can’t win for losing, it seems. Who are our friends, and who is the snake in the grass in Congress. There must always be a villain in the plot. Will it be the outer-space missile this time?”
A search with Google’s Ngram viewer indicates that the use of the expression increased sharply in the 1960s, reaching a peak in the late ’80s and early ’90s.
We’ll end with a more recent example of the usage from Any Woman’s Blues: A Novel of Obsession (2006), by Erica Jong:
“I want to be the best man for you, but you’re never satisfied. Whatever I do, it’s not enough—I can’t win for losing!”