Green’s Dictionary of Slang

to take risks, esp. with a set of rules and regulations.

1861		Burnley Advertiser 16 Mar. 3/2: Our decided conviction is that the most prudent course is to sail as close to the wind as possible, buying and selling only from hand to mouth.
1865		H. Kingsley Hillyars and Burtons (1870) 15: A certain kind of young English gentleman, who has sailed too close to the wind at home, and who comes to the colony to be whitewashed.
1877		Falkirk Herald (Scot.) 9 Apr. 6/1: Keep a sharp look-out, and show a bold face, / Or the foe will be soon on your back, Tom! / Sail close to the wind when you tack, Tom! / We live, while we live, by the pluck that we show.
1882		Derby Mercury (UK) 12 July 6/5: In dealing with revolutionists the government always sail as close to the wind as possible.
1894		Manchester Courier 20 Jan. 9/4: He had no doubt that Mr Asbury’s client wished to sail as close to the wind as possible.
1899		Bath Chron. 14 Sept. 8/5: Where is honesty if a man is recommended by Lord Halifax to sail as close to the wind as possible.
1901		Yorks Eve. Post 17 Oct. 4/2: In order to obtain it the naval architect will sail as close to the wind in the matter of weight as possible.
1922		Rock Is. Argus (IL) 15 Mar. 7/2: This is compelling merchants to sail close to the wind on their purchases.
1937		Nott. Eve. Post 28 Apr. 4/5: To sail close to the wind, [...] therefore, difficult of approach.
1944		Eve. Teleg. (Argus, Scot.) 13 July 8/3: The British [...] are no longer strong enough to sail so close to the wind without running the risk of bringing about a grave crisis.
1979		F. Norman Too Many Crooks Spoil the Caper 215: You’ve been sailing pretty close to the wind yourself and I can do without a load of academic clap-trap.
1989		T. Blacker Fixx 227: I had sailed close to the wind, muddied my hands, skated on thin ice.
1992		in R. Graef Living Dangerously 63: He [...] sailed very close to the wind.