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catch (one) napping
To exploit or capitalize on one's inattention (or, sometimes, literal sleep). We were able to sneak into the building because we caught the security guard napping. I scored a goal after I caught their defenseman napping.
catch someone nappingand catch someone off balance; catch someone up short
to come upon someone who is unprepared; to surprise someone. (See also asleep at the switch.) The enemy soldiers caught our army napping. The thieves caught the security guard napping. I didn't expect you so soon. You caught me off balance. The teacher asked a trick question and caught me up short. The robbers caught Ann off balance and stole her purse.
Surprise, take unawares. This term is often used in the passive, as in The United States was really caught napping the day the Japanese bombed Pearl Harbor. It originated in the mid-1500s as to be taken napping. Also see under off guard.
napping, to be caught/catch
To be surprised off guard, taken unawares. This term began life in the sixteenth century as to be taken napping. “Take Nappynge as Mosse toke his Meare” was the title of a 1569 ballad. The term was included in John Ray’s proverb collection of 1670, in which Ray commented, “Who this Moss was is not very material to know. I suppose some such man might find his mare dead, and taking her to be only asleep, might say, ‘Have I caught you napping?’” Yet Shakespeare and other sixteenth-century writers used the phrase in the modern sense of taking someone unawares; “Nay, I have ta’en you napping, gentle love,” Tranio says to Bianca (The Taming of the Shrew, 4.2).