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Related to to windward: Windward Islands
to windward of (something)
obsolete To or into a more advantageous position in respect of something or some situation. An allusion to sailing (in which it is still used literally), in which it is most advantageous to be on or toward the side from which the wind is blowing. The company's many lawyers have ensured that it remains to windward of the new tax laws.
Farlex Dictionary of Idioms. © 2015 Farlex, Inc, all rights reserved.
Toward an advantageous position, as in We were hoping to get to windward of the situation. This expression transfers the nautical meaning of the phrase, "move in the direction from which the wind blows," to other kinds of undertaking. Its figurative use dates from the late 1700s.
The American Heritage® Dictionary of Idioms by Christine Ammer. Copyright © 2003, 1997 by The Christine Ammer 1992 Trust. Published by Houghton Mifflin Harcourt Publishing Company. All rights reserved.
Into or to an advantageous posture or position.
American Heritage® Dictionary of the English Language, Fifth Edition. Copyright © 2016 by Houghton Mifflin Harcourt Publishing Company. Published by Houghton Mifflin Harcourt Publishing Company. All rights reserved.