sail close to the wind

Idioms  

1. 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.

---

Example Sentences

Fox, who hosts a weekly show on GB News and made the remarks while appearing as a contributor on Wootton's programme on Tuesday, does usually "sail close to the wind", the chief executive said.

From BBC

He called for television that is "confrontational, surprising and upsetting", and urged producers: "Take risks. Sail close to the wind."

From BBC

German football club Kaiserlautern and Danish side FC Copenhagen both sail close to the wind with the abbreviation ‘FCK’, while a new handball venue in Lund, Sweden, was christened the Färs och Frosta Sparbanken Arena – or FFS Arena for short.

From The Guardian

Of course, politicians, like most humans, at times sail close to the wind, and sometimes for understandable reasons – personal, security, confidentiality.

From The Guardian

The taxpayer should worry that this systemically important financial institution continues to sail close to the wind.

From Reuters