sail close to the wind
From Longman Dictionary of Contemporary Englishsail close to the windsail close to the windBritish EnglishRISK to do or say something that is nearly wrong, illegal, or dishonest → sailExamples from the Corpussail close to the wind• They had quite a reputation for sailing close to the wind.• With his own property, it was perhaps easier too for a baron to take risks or sail close to the wind.