The Difficult Patriotic Fighting of the Battle of Long Island

On August 21, as a powerful storm swept across the waters off Long Island, Admiral Sir Richard Howe and his brother, General Sir William Howe, met with their key officers to determine when this assault would be carried out. As some American soldiers were killed by lightning strikes, the British carried out their final plans and analyzed maps and intelligence provided to them by city Loyalists. While the colonists waited on Long Island, columns of British soldiers were given three days’ worth of food, an extra shirt, water and rum. The Hessian officers wore dark blue and green uniforms, removing their rank insignia out of fear that they would be shot by Patriot sharpshooters. While the Continentals felt that the storm would delay British landings, they were sorely mistaken, as enemy supply vessels and warships dispatched 75 landing craft to wage operations against the waiting Americans.

These vessels carried 10 British divisions of soldiers, weapons, artillery guns, carriages, horses and supplies to keep their armies moving and fighting against their enemy. Admiral Howe moved his leadership operations to the British Phoenix to watch the massive movement of his army toward Long Island. By 8:30 a.m., there were more than 4,000 British and Hessian soldiers on shore, with their officers guiding them inland and the landing craft making a hasty return to retrieve additional men. Interestingly, General Lord Charles Cornwallis led his men toward Flatbush, and he fought against the largest colonial failure during this battle and suffered the most powerful British defeat at Yorktown some five years later. The British moved toward American lines with well-organized, well-supplied and well-led British and Hessian forces advancing northward toward the Manhattan coastline and into the interior of Brooklyn.

Still clinging to the belief that this British action was a diversion, the enemy deployed nearly all of its 22,000 troops in Brooklyn. The colonists lightly engaged the British but were quickly pushed back when the British utilized their heavier guns. Panic hit the lines, and the Americans destroyed crops and killed livestock to prevent them from falling into British hands. As civilians withdrew eastward with their possessions to flee the fighting, the Loyalists willingly provided intelligence about the location of the American military. From the Narrows toward Jamaica Bay, a distance of more than eight miles, the British were uncontested as they reached the beaches, looted houses for food and wine, and picked and ate fruit.

Washington ordered four regiments of American troops to reinforce the Patriot lines, but he was too hesitant in Manhattan to shift these forces or move his own command headquarters. Only six weeks after the signing of the Declaration of Independence, civilians watched an American force fall back in havoc as the British began taking 1,000 prisoners of war. Atrocities were committed against these Americans, some of whom were beaten and stabbed to death by Hessian soldiers. Others were later detained aboard the British “Hell Ships.” Observing the poor leadership and fighting abilities of the Continental Army, British officers estimated that the American cause would be quickly defeated and the colonies restored to the empire. Washington misjudged the strength and location of the British forces, and he had limited knowledge of the land his army defended.

Before and during the fighting, Washington replaced three of his commanding generals within five days to meet the superiority of the British. General Nathanael Greene was a Quaker and a well-educated native of Rhode Island who helped besiege the British at Boston and was quickly promoted from private to general. At the Battle of Long Island, Greene became severely ill and was forced to turn over his command authority. This leadership fell upon General John Sullivan, a lawyer from New Hampshire who was known for his financial disputes. He was promoted to the rank of general and fought in the Siege of Boston, but he was quickly replaced by Washington for a lack of fighting understanding. The third commanding leader was Israel Putnam, a lieutenant colonel in the French and Indian War who fought against the Spanish in Cuba. This major general became an ardent Patriot during the Stamp Act crisis and was expected by Washington to oppose the British onslaught. Putnam still utilized Sullivan in the field to observe the forward outposts and the enemy’s rapid movements.

These changes in the face of the enemy demonstrated concerns about the inability of the American leadership to make vital decisions and carry them out against the British. The Patriots were forced back from the Heights of Guana, hills that extended from Bay Ridge, Brooklyn, through Queens. These hills climbed 150 feet and contained four possible military passes at Gowanus, Flatbush, Bedford and Jamaica. But these natural barriers, with a mixture of fortifications and thinly held lines, quickly fell, forcing the Americans back to Brooklyn Heights. Washington ordered the plugging of holes against the enemy, but the Americans were overmatched in front of and behind their lines by British troops who seemed to be everywhere. With only about 8,000 soldiers to defend against this invasion, the Americans could only “harass” and “slow down the enemy,” while Washington watched from an elevated position as the strength of the Redcoats advanced against his soldiers.

With the Americans facing the grim prospect of being overrun by the enemy, Washington’s only positive news was provided by the First Maryland Regiment. On August 27, 1776, Generals Alexander and Sullivan led 400 men against 2,000 British troops at an old Dutch farmhouse in Brooklyn. Cannons and guns from both sides targeted each other and caused serious losses. At certain points, the fighting proved that Americans would defend their positions against superior forces. Through their ability to flank the Americans, the British easily captured American prisoners of war. The British used force to move in on the soldiers and caught Sullivan brandishing two pistols in a grain patch.

General William Howe refused to push forward against the beleaguered Patriots and reasoned that Washington still had reinforcements in Manhattan that could be called into Brooklyn. He also feared that his men would suffer from this attack and that it would take too long to obtain additional men from England. Dissenting opinions called for an attack to finish off the three miles of land that Washington barely held. On August 29, Washington met with his generals, and they decided to retreat with the remaining parts of their army to Manhattan. The soldiers were ordered to remain silent and show no signs of movement that could alarm the British Redcoats. In an American effort that resembled the British operations at Dunkirk, fishermen from Marblehead, Massachusetts, skillfully carried out the operation to transport and save the bulk of the army.

As fog settled upon this naval retreat, Setauket native Lieutenant Benjamin Tallmadge stated, “I could scarcely discern a man at six yards’ distance.” Howe waited and presented no opposition as, close to the prying eyes of his army, 12,000 Americans were transported to Manhattan to fight another day. Putnam marveled at the inability of the British leader to respond, observing, “General Howe is either our friend or no general. He had our whole army in his power … and yet suffered us to escape with the least disruption.”