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to sail close to the wind

to sail close to the wind

1 8.1
To do something risky that almost breaks rules or laws
  • idiom
  • Informal
translation icon : navegar al límite
  • The company was accused of sailing close to the wind by exploiting loopholes in the tax code.

Examples

  • In her competitive business dealings, she often sailed close to the wind, risking her reputation.

  • Your friend Billy Norton is sailing close to the wind.

  • You're sailing close to the wind, Billy.

  • 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 play with fire
vsto sail close to the wind
  • Informal
22 5.8

To take a big risk that can cause harm

focuses on risking rule or law limits rather than mere danger
to throw caution to the wind
vsto sail close to the wind
  • Informal
7 7.3

Do something without worrying about the risks

pushes close to legal and ethical limits rather than mere recklessness
to play fast and loose
vsto sail close to the wind
  • Informal
6 8.0

Act in a careless way by ignoring rules and other people's feelings

deliberately flouts rules and risks legal or ethical breach
to dance with the devil
vsto sail close to the wind
  • Informal
1 9.6

To take a serious risk by doing something morally wrong to gain power or money

focuses on nearing legal or ethical limits rather than seeking profit
close to the wind
vsto sail close to the wind
8.6

Behaving in a way that is risky or near the limit of what is allowed

pushes limits toward rule breaking and unethical behavior

Antonyms

Do what a rule says

Choose a careful option to avoid risks

How Risky

to sail close to the wind
  • Informal
1 8.1

Surface Forms

sailed close to the wind past participle
sailing close to the wind present participle
sails close to the wind third person singular

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'.