to sail close to the wind
- idiom
- Informal
- The company was accused of sailing close to the wind by exploiting loopholes in the tax code.
Examples
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In her competitive business dealings, she often sailed close to the wind, risking her reputation.
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Your friend Billy Norton is sailing close to the wind.
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You're sailing close to the wind, Billy.
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The police seem to find it okay to defy their Commissioner's orders, break police department policy, and even sail close to the wind in breaking the law when they have an industrial campaign going in the pursuit of more money.
Blog text (23) -
The politician was criticized for sailing close to the wind with his controversial comments.
Synonyms
To take a big risk that can cause harm
Do something without worrying about the risks
Act in a careless way by ignoring rules and other people's feelings
To take a serious risk by doing something morally wrong to gain power or money
Behaving in a way that is risky or near the limit of what is allowed
Antonyms
How Risky
- Informal
Surface Forms
Morphology
sail + close + to + the + wind
The phrase uses a nautical metaphor — literally sailing very near the wind is a risky seamanship tactic — so there is a plausible link between the constituents and the idea of doing something near a danger or limit. However the extension to borderline unethical or rule‑breaking behaviour is metaphorical and domain‑specific, so a B1 learner who knows the words might guess 'near danger' but would not reliably infer the precise pragmatic meaning without prior exposure.
Etymology
The idiom sail close to the wind comes from real sailing: to sail very near the wind is dangerous because the boat can lose control, so sailors who did this were taking a risky move. That's why the phrase now means 'to act in a risky way' or 'to almost break the rules'.