George Washington was a gambling man. Although the Father of Our Country once called gambling “the child of avarice, the brother of iniquity, and the father of mischief,” that did not stop him from testing the odds in all manner of pursuits such card playing and lotteries. His willingness to take risks, however, did not end at the card table. As a general, Washington used feints, intelligence networks, and strategic deception whenever he could to eke out an advantage over his enemy the British, then the most potent military power in the world. Little wonder that one of the phrases he wrote to a disheartened fellow officer during the American Revolution was, “Perseverance and spirit have done wonders in all ages.”
One of Washington’s greatest gambles resulted in ultimate victory over British forces — in fact, some historians suggest it was the most important decision he ever made as a military man. In 1781, General Jean-Baptiste Rochambeau led French troops that joined with the Continental Army during its summer encampment on the Hudson River near the town of Dobbs Ferry, New York. The French believed the American army was running out of time as it lost men and the ability to remain adequately supplied in a war that could not continue much longer. An attack on Manhattan and the British forces there was the more feasible and logical target for the combined armies. But, it was also where the British expected the blow to fall. A long-shot, but a long-shot worth taking, was the strategy of marching the combined armies out of New York and then head for Virginia where Washington and Rochambeau could trap General Lord Cornwallis at Yorktown. Washington’s joint armed forces would be supported by the French Navy under Admiral Francois de Grasse, whose armada would take possession of Chesapeake Bay and leave Cornwallis with no escape. The result was “the world turned upside down” American victory familiar to any school kid who paid attention in his U.S. History class. Cornwallis surrendered, the British were in shock, and George III’s government began negotiations that led to the end of the war and recognition of American independence.
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