It's a bizarre expression that I've always taken to describe a situation in which one has very nearly achieved their objective. Where do the roots of this expression lie?
closed as general reference by Kristina Lopez, James McLeod, tchrist, kiamlaluno, MετάEd Feb 25 at 16:07
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A cigar, as a luxury, is often awarded and smoked to celebrate a success, in much the same way that champagne is drunk.
The earliest quotation in the OED is from the Cleveland (Ohio) Plain Dealer of March 6th, 1930:
I found a slight antedating in the Princeton Alumni Weekly (Volume XXIX, No. 36 - Page 1166) of July 2, 1929:
Barry Popik's The Big Apple includes a brief history of awarded cigars:
A slightly earlier citation is given, from the Long Island Daily Press (Jamaica, NY) of 18 May 1929, as a headline: