sail close to the wind

S

sail close to the wind (idiom)
/seɪl kloʊs tu ðə wɪnd/

Meaning

  • To engage in actions that are risky or verge on being illegal or improper.
  • To operate perilously near the boundary of acceptable or lawful behavior.
  • To perform deeds that are hazardous or barely within legal or ethical limits.
  • To navigate a vessel as near as possible to the direction from which the wind is blowing, while still making headway.

Example Sentences

  1. The journalist sailed close to the wind by publishing classified information but avoided legal action.
  2. By exploiting tax loopholes, the corporation sailed close to the wind in its financial dealings.
  3. His frequent late arrivals at work sail close to the wind of the company’s punctuality policy.
  4. The politician’s comments sailed close to the wind, bordering on hate speech.
  5. In an attempt to win the game, the coach’s strategies sailed close to the wind, pushing the limits of fair play.

Origin and History

The phrase “sail close to the wind” originates from nautical terminology. In sailing, to “sail close to the wind” means to steer the boat as near as possible to the direction the wind is coming from.

This maneuver, known as sailing close-hauled, requires skill to maintain progress without being pushed backward.

Figurative Evolution

Over time, this nautical term evolved into a metaphor describing actions that approach the limits of legality or propriety. The analogy lies in the precarious balance required in both sailing close to the wind and engaging in risky behavior that skirts the boundaries of acceptable conduct.

Earliest Recorded Usage

The figurative use of “sail close to the wind” dates back to the first half of the 1800s. However, the exact earliest printed record of the term is not available.

Synonyms

  1. skate on thin ice
  2. walk a tightrope
  3. push the envelope
  4. flirt with danger
  5. test the limits

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