In August of 1776, General Washington and General Howe squared off in what was an inevitable defeat for the Americans in Long Island, which led to the battle for New York City.
Washington's Continental Army was greatly outnumbered by the British, and calling them an Army is a bit of an overstatement as they weren't much more than a disorganized militia.
Nonetheless, shrewd tactics on the part of the Americans – combined with favorable weather and a lot of luck – saw the patriots avoid a strategic defeat.
That summer, Washington's men were backed into Brooklyn where they had to defend potential attacks coming from land as well as from the East River. General Howe led 15,000 men, including 8,000 Hessian mercenaries whereas Washington had about 9,000 men under his command, with two thousand of them lacking weapons to fight with. Perhaps the most professional force serving with the patriots was Knowlton's Rangers, led by a Thomas Knowlton.
In late August, a major battled broke out on Gowanus Road. The British preferred to soften up the flanks of enemy formations with volleys of fire, encircle them, and then charge forward with fixed bayonets.
Washington's men were forced to continue breaking contact in order to avoid this fate before they managed to make it to high ground. From there, they repelled three British advances in what is known as Battle Hill.
Unknown to Washington at the time, General Howe had taken a contingent of his forces and executed a rather bold maneuver. Using a local to guide his men through Jamaica Pass, which was little more than a swamp, his forces suddenly appeared at the rear of Washington's formations. The American forces suffered losses, had several captured, and others ran at a full sprint deeper into Brooklyn.
That day by mid-morning, Howe had his ships-of-the-line attempt to sail up the East River. The intent was to hit Washington's men in a sort of pincer movement, attacking from both the land and the sea. The patriots surely would have been cut to pieces if caught in this double envelopment.
It was one of those curious moments in history in which the fate of the American revolution seemed to hinge on which direction the wind was blowing that day.
The British found themselves battling both the wind and the tide, and only a few small ships were able to get within cannon range of the American redoubt in Red Hook. It was hardly the stunning maneuver that Howe was hoping for.
Patriot forces continued to clash with the British until their backs were pushed up against the East River. The British began digging trench lines as Howe prepared his coup de grace which would put down the rebellion once and for all.
However, Washington had another trick up his sleeve: a masterstroke of military deception.
Washington ordered every boat that could be sequestered from the area to be used to transport his men across the river to Manhattan in the dead of night. Campfires were kept burning throughout the night to make the British believe that they remained stationary in their own fortifications.
Once in Manhattan, Washington faced another unwinnable and impossible dilemma. The British dominated the sea, making an escape by ship untenable. If Howe landed men to the North in Westchester County, Washington's men would be trapped on the island with few defensible terrain features.
Several weeks passed as the British and the patriots stared at each other from across the East River until the invasion of Manhattan began on September 14. Washington had just 3,500 men under his command by this point when what militia remained began to panic. Some were bayoneted by the British as they attempted to surrender.
As his men cut and run, they threw down their weapons and fled. In a letter he wrote of the incident later, Washington describes the affair as, "disgraceful and dastardly."
On Sept. 16, the Battle for Harlem Heights began, with Knowlton's Rangers still willing to put up a fight. They executed bold flanking maneuvers that harassed the British, but their small numbers were eventually repelled by counterattacks. The British also had the advantage of Naval gunfire support from their ships that were now able to make it into the East River.
Washington ordered a retreat. His men crossed the East River to the North with the British still in pursuit, eventually leading to the Battle for White Plains.
To call Washington's battle for New York City a defense in-depth, a tactic designed to wear down the enemy through a series of organized withdrawals and attrition would be too charitable.
At times it was a complete breakdown of anything resembling military discipline but as is often remarked about General Washington, he lost nearly every battle he fought in but still won the war.
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