sail close to the wind

sail close to the wind (do or say smth that is nearly wrong, illegal, dishonest or not acceptable) — играть/ действовать на грани фола, на грани провала; рисковать; подвергать риску; ходить по краю пропасти; еще чуть-чуть и...|| рассказывать рискованный анекдот

Example 1: We may have just enough fuel to get there, but we'll be sailing a bit close to the wind. (often in continuous tenses) (CIDI) — ... но это будет слишком рискованно; но это большой риск.

Example 2: I was sailing pretty close to the wind when I called him a thief.

Example 3: I think he realized he was sailing a little too close to the wind in his business deals, but he claimed everything was legal.

see also
[be asking for trouble]
[ride for a fall]
[отделаться легким испугом]
[narrow escape]
[балансировать на грани]
[close call]
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This term alludes to the danger incurred when literally sailing too close to (that is, in the direction of) the wind. (Answers.com)