There are fourteen large winches on the decks of Jim Hurlock’s sailboat, White-Jacket, a 51-foot sloop of heroic proportions, with a mast as tall as an apartment house and a boom that could decapitate a Clydesdale. There are a half-dozen thick ropes threaded through pulley blocks and wrapped on the winches, tugging the sails against their natural inclination to turn into giant flags. There are ten people on the deck, plus Hurlock himself at the wheel, tending to the moving parts of this fabulously complex machine that is propelling itself across Block Island Sound at around six knots. Six knots on land would be a brisk jog, but speed as such is not the point of sailing, as Hurlock sees it. The goal is to go just fast enough to beat the other boats.

Hurlock is sailing against the wind, on a zigzag course toward a race buoy bobbing in the distance. He is preparing to tack, which means he will turn the bow so the wind blows from the other side of the boat. A series of tacks, alternating left and right, is how a sailboat accomplishes the miracle of traveling east while the wind is trying to blow it west. Sailboat races are won or lost on the crew’s skill in maneuvers such as this. You can’t go faster than the wind, which blows equally hard on the accomplished and the incompetent. As a lawyer, Hurlock appreciates the rough justice of this. As the owner of one of the largest and heaviest boats in the race, though, he would prefer that it blew on everyone at about 20 knots, rather than eight.

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