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sail close to the wind

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Be on the verge of doing something illegal or improper, as in She was sailing pretty close to the wind when she called him a liar. This term alludes to the danger incurred when literally sailing too close to (that is, in the direction of) the wind. Its figurative use dates from the first half of the 1800s.

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The American Heritage® Idioms Dictionary Copyright © 2002, 2001, 1995 by Houghton Mifflin Harcourt Publishing Company. Published by Houghton Mifflin Harcourt Publishing Company.

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