English

Adjective

close to the wind ‎(comparative closer to the wind, superlative closest to the wind)

1. Used other than as an idiom: see close to,‎ the,‎ wind.
2. Near a limit of feasibility or compliance with law or morality.
   • 1983, Colin Watson, Six Nuns and a Shotgun, page 167:

     I mean, I shouldn't be altogether flabbergasted if you were to tell me that there had been tax fiddles here, or even something a bit close to the wind where the play and the girls are concerned.

   • 2000, David S. Bell, Presidential Power in Fifth Republic France, page 116:

     Coming on the heels of revelations about financial and property dealings a bit close to the wind in other sections of the Gaullist Party, the authority of the Prime Minister could not but be weakened

Adverb

close to the wind ‎(comparative closer to the wind, superlative closest to the wind)

1. Used other than as an idiom: see close to,‎ the,‎ wind.
2. (nautical) In a direction almost opposite to that from which the wind is blowing
3. Near a limit of feasibility or compliance with law or morality.
   • 1850, F. W. Cukbey., “Against All Odds”, in The Dublin university magazine, page 306:

     Time you want a real good friend is when you're gone just a bit close to the wind, and want to be set right again.

   • 2003, Richard K. Morgan, Altered Carbon, page 150:

     Miriam's wordplay was steering fractionally too close to the wind for my liking.

   • 2004, James R. Acker, David C. Brody, Criminal Procedure: A Contemporary Perspective, page 422:

     This means, naturally, that a prosecutor anxious about tacking too close to the wind will disclose a favorable piece of evidence.

   • 2011, “Warnock slams ref as Dunne own goal gifts QPR point”, in Irish Independent:

     As far as an FA charge goes, Warnock sailed closest to the wind in his initial, expansively voiced televised criticism of Oliver -- the youngest Premier League ref at 26