Q From Frank Danielzik, Germany: I know what to hoodwink means, but cannot imagine how it came about. There seems no connection between its meaning and the individual words it is made up from.
A The original sense of hoodwink was to prevent somebody seeing by covering their head with a hood or blindfolding them. Our main sense now is a figurative one derived from it, to deceive or trick (as we might also say, to pull the wool over someone’s eyes), which appeared in the early seventeenth century.
There’s no problem with the first part, but wink here isn’t in the sense we use now of closing and opening one eye quickly as a signal of some sort. When it first appeared, in Old English in the form wincian, it meant to close both eyes for some reason, or to blink, or close the eyes in sleep (hence forty winks). A hoodwink forcibly lost somebody the power of sight as though they had closed their eyes. And hoodwink was long ago an alternative name for blind man’s buff.
When we say that somebody winks at some offence, meaning that they connive at it, we’re also using a relic of the same sense. And long before wink became a flicker of one eyelid it meant a significant glance instead. If you find something written before the nineteenth century that says one person winked at another, a glance is what’s meant — both indicate that the person is sending a message, but the method is slightly different. Today’s meaning first appears in The Pickwick Papers by Charles Dickens, 1837: “Mr. Weller communicated this secret with great glee, and winked so indefatigably after doing so, that Sam began to think he must have got the ‘tic doloureux’ in his right eyelid.”
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