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to gain the wind
From The Collaborative International Dictionary of English v.0.48:
Gain \Gain\, v. t. [imp. & p. p. Gained (g[=a]nd); p. pr. & vb. n. Gaining.] [From gain, n. but. prob. influenced by F. gagner to earn, gain, OF. gaaignier to cultivate, OHG. weidin[=o]n, weidinen to pasture, hunt, fr. weida pasturage, G. weide, akin to Icel. vei[eth]r hunting, AS. w[=a][eth]u, cf. L. venari to hunt, E. venison. See Gain, n., profit.] [1913 Webster] 1. To get, as profit or advantage; to obtain or acquire by effort or labor; as, to gain a good living. [1913 Webster] What is a man profited, if he shall gain the whole world, and lose his own soul? --Matt. xvi. 26. [1913 Webster] To gain dominion, or to keep it gained. --Milton. [1913 Webster] For fame with toil we gain, but lose with ease. --Pope. [1913 Webster] 2. To come off winner or victor in; to be successful in; to obtain by competition; as, to gain a battle; to gain a case at law; to gain a prize. [1913 Webster] 3. To draw into any interest or party; to win to one's side; to conciliate. [1913 Webster] If he shall hear thee, thou hast gained thy brother. --Matt. xviii. 15. [1913 Webster] To gratify the queen, and gained the court. --Dryden. [1913 Webster] 4. To reach; to attain to; to arrive at; as, to gain the top of a mountain; to gain a good harbor. [1913 Webster] Forded Usk and gained the wood. --Tennyson. [1913 Webster] 5. To get, incur, or receive, as loss, harm, or damage. [Obs. or Ironical] [1913 Webster] Ye should . . . not have loosed from Crete, and to have gained this harm and loss. --Acts xxvii. 21. [1913 Webster] Gained day, the calendar day gained in sailing eastward around the earth. To gain ground, to make progress; to advance in any undertaking; to prevail; to acquire strength or extent. To gain over, to draw to one's party or interest; to win over. To gain the wind (Naut.), to reach the windward side of another ship. Syn: To obtain; acquire; get; procure; win; earn; attain; achieve. Usage: See Obtain. -- To Gain, Win. Gain implies only that we get something by exertion; win, that we do it in competition with others. A person gains knowledge, or gains a prize, simply by striving for it; he wins a victory, or wins a prize, by taking it in a struggle with others. [1913 Webster]