George Washington’s Dramatic Roll of the Dice That Greatly Impacted Westchester

On February 22, 1781, George Washington awoke to his 49th birthday with little to celebrate. Winter winds had frozen progress for the rebelling colonies to a near standstill. The young republic wobbled through supply draughts, vicious counter-attacks, and regular mutinies. Public opinion was chilling over, too. The general lamented to South Carolina statesman John Laurens that “the people are discontented…but it is with the feeble and oppressive mode of conducting the war, not with the war itself.” 

In the summer, the situation seemed to worsen as talks of a treaty echoed through Versailles, France. Washington knew the terms of a treaty could be crippling, including continued British control, sustained conflict, territory loss across the South and West, and curtailed tactical and material support from Paris. With few other options, John Adams and Ben Franklin prepared their quills. 

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Beginning July 4, 1781, Washington set up headquarters on the Ardsley/Hartsdale border. While the Americans held down the west around Dobbs Ferry (which Pulitzer Prize-winning historian David Hackett Fischer called “the crossroads of the Revolution”) and Ardsley, the French allies hunkered down east of the Sprain Brook near Hartsdale and White Plains. The high ground was defensible and afforded movement south to New York City, northwest to King’s Ferry, or north to New England’s forests. 

General Washington hoped that, together, the forces could drive British General Henry Clinton from Manhattan. Two elite units—the Light Infantry (the nation’s first national military organization, composed of each local militia’s 100 best men) and the Dragoons—sharpened their bayonets along what is now the Bronx River. Still, American spies deemed any campaign against Manhattan a long shot. The revolutionaries were outnumbered and the British expected an attack. 

Then in August, Washington received a letter from French Admiral Françios Joseph Paul de Grasse that historian Robert Leckie called “possibly the most momentous message of the entire war.” De Grasse would sail his large fleet north from the West Indies to Chesapeake Bay. 

For Washington, it brought a titillating opportunity, but an incredible risk. Victory meant a multi-pronged surprise assault on General Cornwallis at Yorktown, Virginia. Although it could be the scale-tipping conquest Washington coveted, he preferred Westchester. The general wrote that “[m]atters having now come to a crisis and a decisive plan to be determined on, I was obliged…to give up all idea of attacking New York.”

Reaching Virginia in time would require a deadening 400-mile march. And if news of the advancing allied armies and fleets reached General Clinton, he would tip off General Cornwallis. Still, Washington rolled the dice. Plans to charge on Manhattan from the Bronx River faded. On August 19, the French and Americans decamped and headed south. To outfox the Redcoats, Washington sent a decoy along the Jersey shore to feign a raid on Staten Island. Landing craft paraded below Westchester to bolster the rumor. 

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Just two months later, Cornwallis surrendered his army of 7,500 men at Yorktown. The Revolution had triumphed. In the words of Dobbs Ferry Village Historian Richard Borkow, “Washington’s great gamble of mid-August, 1781, determined the fate of our Republic.” Westchester was the very staging ground for this victory. The Hudson’s hills were a military fault line where seismic events could have erupted, for the Battle of Yorktown was almost the Battle of Westchester. 

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