close to the wind

comparative closer to the wind · superlative closest to the wind

1. figurativelyNear a limit of feasibility or compliance with law or morality.

   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.

   1983, Colin Watson, Six Nuns and a Shotgun, page 167

   1 more example

   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

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

2. Used other than figuratively or idiomatically: see close to, the, wind.

comparative closer to the wind · superlative closest to the wind

1. nauticalIn a direction almost opposite to that from which the wind is blowing.
2. figurativelyNear a limit of feasibility or compliance with law or morality.

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

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

   3 more examples

   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.

   1850, F. W. Cukbey., “Against All Odds”, in The Dublin University Magazine, page 306

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

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

   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

   2011 September 26, “Warnock slams ref as Dunne own goal gifts QPR point”, in Irish Independent

3. Used other than figuratively or idiomatically: see close to, the, wind.