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Sailing within the Wind
or Sailing close to the Wind. Going to the very verge of
propriety, or acting so as just to escape the letter of the law. The
phrase, of course, is nautical.
“The jokes [of our predecessors] might have been broader than modern
manners allow, but ... the masher sails nearer the wind than did his
ruder forefathers.” —Nineteenth Century, November, 1892, p.
795.
“Ea defended himself by declaring that he did not tell Hasisadra
anything; he only sent her a dream. This was undoubtedly sailing very
near the wind.” —Nineteenth Century, June, 1891,
p. 911.
Source: Dictionary of Phrase and Fable, E. Cobham Brewer, 1894 More on Sailing within the Wind from Infoplease:
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