Meaning
To come very near the limit of what is lawful, moral, or acceptable; to follow a course that only just avoids breaking rules, giving offence, or inviting disaster. Typically said of conduct that is risky or dubious rather than outright wrong. Usually mildly disapproving, though it can carry grudging admiration for audacity; it implies near-transgression, not actual wrongdoing. Regional use: General English.
Origin
A genuine artefact of sail handling. No sailing vessel can travel straight into the wind, so crews steered as near the wind's direction as the sails would still draw - close-hauled, or close by a wind - moving fast on the very edge of failure, since a small error in heading put the bow dead into the wind and the sails lost all drive; in modern yachting terms the boat enters the no-go zone of roughly thirty to fifty degrees either side of the wind and is said to be in irons. Dated evidence for the technical expression comes early: Captain John Smith's seamanship manual A Sea Grammar (1627) discusses sailing against the wind, lying close by a wind, and beating up upon a tack in the wind's eye, noting that a square sail cannot come nearer the wind than six points. The figurative sense - steering as near to wrongdoing or impropriety as possible without quite entering it - grew out of this technical language and has been common in print since the nineteenth century, though the accessible references do not pinpoint a first clearly figurative citation.
Research Sources
References used to check this entry’s meaning, history, or documented forms.
Variants
- close to the wind
- sail near the wind
- sailing close to the wind
Usage Examples
- His expense claims always sail close to the wind, legal enough to avoid fraud yet generous to a fault.
- The comedian sails close to the wind with material about her own family, but she never quite crosses the line.
- Their trading desk sailed close to the wind for years before the regulator finally rewrote the rulebook.