On his own initiative or perhaps under direct orders, Captain Alexander Hamilton laid plans to launch a daring night raid with the arrival of warmer and less rainy weather just after mid-June 1776, after the spring rains had stopped. Envisioning a surprise attack, he targeted the British defensive position around the lighthouse at the northern end of Sandy Hook, New Jersey, south of New York Harbor and just southeast of Staten Island. Situated at the entrance of New York harbor, Sandy Hook, a thin peninsula that thrust north from the New Jersey mainland, was a strategic position. Hamilton struck in the darkness in an assault in which he carefully coordinated the fire of his New York artillery pieces and infantry attackers. Conducting his first offensive strike, the young captain mixed musketry with artillery fire of approximately one hundred men, taking advantage of the darkness and the element of surprise. But the enemy’s defensive position was too strong to be overcome. Hamilton revealed his trademark hard-hitting style: “I continued the attack for two hours with [his New York] fieldpieces and small arms, being all that time between two smart fires from the shipping [British warships just outside Sandy Hook] and the [defensive position around] the lighthouse, but could make no impression on the walls” of the British defensive position. This sharp clash at Sandy Hook has become one of the forgotten fights of the American Revolution.
Meanwhile, Washington was placed in a no-win situation by the rising chorus of demanding politicians of the Continental Congress and the impossible mission of defending New York City. Because Manhattan Island was surrounded by a network of waterways, Washington was unable to develop an adequate tactical solution for defending the city. Nothing could counter the powerful Royal Navy, which guaranteed that America’s largest city would fall, after England had dispatched the largest fleet and expeditionary force ever set forth, under General William Howe. On June 28, and not long after he returned from his Sandy Hook raid, Hamilton watched the execution of Irishman Sergeant Thomas Hickey in lower Manhattan, near the Bowery, for his role in a plot to murder General Washington in a city swarming with Loyalists. Hamilton fully approved the execution that he hoped would cow “those miscreants,” the large Tory population of New York City.
In early July, General William Howe finally made his first tactical move, disembarking thousands of British and Hessian troops onto Staten Island from warships of his brother Lord Richard Howe’s fleet. Hamilton and his gunners saw their first action on July 12, barely a week after the signing of the Declaration of Independence in Philadelphia. The spirits of Hamilton and his men were high, after Washington announced the issuing of the declaration to his troops assembled on the New York City Common, where the native West Indian had made his impassioned speech two years before. Still smarting from having recently lost his purse containing his officer’s pay, (which happened on July 6, perhaps from too much drinking from America’s first Fourth of July celebration), Hamilton might have been in a bad mood. If so, he was presented with an opportunity to finally unleash his wrath on the enemy.
Two British warships, the Rose and the Phoenix of the powerful fleet of Admiral Richard Howe, the brother of General William Howe, caused panic on Manhattan Island by sailing up the Hudson to probe the strength of the American defenses, including Fort Bunker Hill. Nothing could stop the two warships that demonstrated the tactical superiority and skill of the British Navy: an ill-omen for American forces in regard to attempting to defend a city surrounded by waterways. From this high point on Manhattan Island, Hamilton gave the command to fire. His men opened up with their guns at the British vessels. King George III’s sailors returned fire upon Hamilton’s earthen fort atop the commanding heights. Because of inferior artillery in terms of caliber, Hamilton’s resistance proved largely ineffective, allowing the two warships to continue sailing up the broad Hudson. Several New York artillerymen were injured when the barrel of one Hamilton’s guns exploded, most likely because the barrel was defective because of age or inferior quality. Contrary to the opinions of some historians, Hamilton was not at fault for what was nothing more than an accident.
With an elaborate defensive network protecting New York City that Washington attempted to hold in the hope of inflicting another defeat like at Bunker Hill (Breed’s Hill just outside Boston)—if General Howe was foolish enough to order frontal assaults as on that bloody day last June—the British wisely refused the bait of launching infantry attacks. Unfortunately, feeling that he had to face the British Army’s might—now swollen to forty-two thousand men to outnumber Washington’s Army—partly because this upcoming confrontation was a “point of honor” and under political pressure from the Continental Congress to defend New York City, Washington was already in serious trouble long before the first shot in the showdown for New York City was fired in anger. He had dispersed his troops over a wide area to defend Manhattan and Brooklyn, which Hamilton correctly believed was indefensible. In fact, this precocious young man sensed the fast-approaching disaster, because Washington had divided his army, which was now separated across a sizeable body of water, the Upper Bay just below the East River.
Finally, Howe struck when he felt the opportunity was right. The Royal Navy sailed from Staten Island and landed thousands of troops on the southern end of Long Island at Gravesend Bay. After coming ashore via new, innovative landing crafts on the warm morning of August 22, Howe’s troops then skillfully maneuvered inland. Around seventeen thousand British and Hessian soldiers marched seven miles to the northeast to outflank American defensive positions, and eased themselves into an ideal position to strike Washington’s rear south of Brooklyn Heights, to catch the badly outnumbered homespun rebels by surprise. Lord William Howe’s professional troops struck a powerful blow that sent the American forces reeling on August 27 during the battle of Long Island.
Meanwhile, maintaining his longtime defensive position on Manhattan Island to the northwest, Hamilton and his New York gunners from atop Bayard’s Hill, the highest point in the city, listened to the battle roaring on Long Island. Washington was driven to new levels of frustration by the rout. The embarrassing defeat—a new low for the novice Continental Army and the largest battle to date—showed that the amateurs in rebellion (this was Washington’s first experience in commanding an army in a sizeable battle) were no match for well-trained troops led by experienced, professional leaders.
After the survivors of the disastrous battle of Long Island were transported west in flat-bottomed boats by Colonel John Glover’s New England mariners across the mist-covered East River on the night of August 29 to Manhattan Island’s safety during the narrow escape, Washington still attempted to hold the strategic island, which only guaranteed the same inevitable bleak results, because of the Royal Navy’s vast superiority. However, the sound arguments of his top lieutenant, General Nathanael Greene, had convinced the commander-in-chief otherwise. Washington wisely decided to abandon New York City before it was too late, because the British Navy could land large numbers of troops north of Washington at anytime to trap his army on Manhattan Island. At a commanders’ conference on September 12, it was decided that the army of ill-trained troops, who were no match for redcoat regulars, should retreat north up the Hudson to the easily defendable high ground of Harlem Heights.
Two young officers who would win distinction in the years ahead played key roles in protecting Washington’s withdrawal (“I was among the last of our army that left the city” bragged Hamilton for good reason) northward up Manhattan Island. After sailing up the East River, Howe’s forces landed at Kip’s Bay, around nine miles southeast of Harlem Heights, on a Sunday that Washington never forgot. What happened at Kip’s Bay was an alarming reminder of what could also happen on the island’s west side along the Hudson, because of the Royal Navy’s strength and capabilities: the British could land large numbers of troops at will north of Washington’s Army to cut-off escape from Manhattan Island. Here, at this natural indentation located on the island’s east side above New York City, a heavy cannonade of nearly eighty guns from Admiral Howe’s warships and the unnerving sight of thousands of British-Hessian troops rowing toward shore in barges caused a rout of the raw New England soldiers on September 15, 1776. Without losing a single soldier, Howe succeeded in negating the American riflemen in defensive positions—the old Bunker Hill formula for success—with a massive artillery bombardment.
But two highly capable young officers had restored a measure of honor to the Continental Army during the dismal withdrawal. As a strange fate would have it, the destinies of Hamilton and Aaron Burr were already intertwined on the American stage by the time of the retreat to Harlem Heights. Despite now wearing Continental officer uniforms of blue, one of these promising men was destined to take the other’s life in a little more than a quarter century. Hamilton’s New York battery had been now reduced in firepower, after having been forced to leave their heavy guns behind, at Fort Bayard, after Washington had issued orders for New York City’s evacuation. Therefore, Hamilton now commanded only three light guns of his reduced New York battery.
A historian before he became the nation’s twenty-sixth president in September 1901, Theodore Roosevelt emphasized the value of the Hamilton-Burr connection in protecting Washington’s vulnerable rear during his withdrawal north from New York City. Washington’s “divisions, on their retreat, were guided by a brilliant young officer, Aaron Burr, then an aide-de-camp to [General Israel Putnam, while the army’s] rear was protected by Alexander Hamilton and his company of New York artillerymen, who in one or two slight skirmishes beat off the advance guard of the pursuers.”
During the cheerless withdrawal north to Harlem Heights, and assisted by Burr’s knowledge of the road leading north, Hamilton repeatedly rose to the challenge of protecting the army’s rear, demonstrating leadership abilities noticed by his superiors, including Washington. As planned, Washington took good defensive position on the commanding ground of Harlem Heights just over a dozen miles north of New York City. He naturally hoped that Howe would commit the folly of assaulting the fortifications situated atop dominant terrain. Fulfilling his rearguard role for the army, young Captain Hamilton was one of the last Americans to reach the safety of the new defense line. Forced to drag their guns because artillery horses had been lost, he and his New York gunners arrived after dark on another warm September night with their two New York cannon, after one of his guns broke down and had to be left behind, along with the artillery unit’s baggage. Only because the British pursuit lacked vigor, Hamilton was fortunate not to have been captured.
Here at the rocky plateau known as Harlem Heights, including bluffs ascending to a height of around sixty feet, was a panoramic view of the southern end of Manhattan Island, where Hamilton selected a good position in Washington’s newly constructed defensive line and carefully placed his two light guns for the best fields of fire. Even the survivors of the Kip’s Bay disaster were emboldened by Washington’s high ground defensive position brimming with artillery, including Hamilton’s New York guns. Washington again viewed Hamilton’s organization skill and military bearing at his new defensive position that had been bolstered by light earthworks to protect his two cannon. Washington was impressed by what he saw.
But Howe had learned his Bunker Hill lesson well on June 1775, and never forgot his frightfully high losses. He refused to take the bait of attacking the formidable Harlem Heights, although fighting did erupt on September 16. Once again, the Royal Navy landed large numbers of Howe’s troops north of Washington’s stationary position to negate the high ground advantage. The out-maneuvered revolutionaries were once again forced to withdraw north from Harlem Heights toward Manhattan Island’s upper tip, when the leaves of October had already turned to their autumnal hues of red and gold, especially the maples, to reveal a natural beauty that seemed to mock America’s sinking military fortunes and the creeping darkness that surrounded the increasingly vulnerable life of an infant republic.