The Battle of Long Island required a stroke of providence to stave off disaster for the American cause less than two months after independence was declared.
The Battle of Long Island required a stroke of providence to stave off disaster for the American cause less than two months after independence was declared.
O n this day 250 years ago, the largest battle of the Revolutionary War was fought. The Battle of Long Island, fought mostly in the heart of modern-day Brooklyn — and sometimes denominated the Battle of Brooklyn — was a smashing victory for the British and a nearly catastrophic American loss that would have ended the war.
When the American Congress issued the Declaration of Independence in July 1776, things were looking up. Sure, Americans had yet to bring any allies openly into the war — declaring independence was a first step in that direction — and their wintertime invasion of Quebec had proved a disaster that Ben Franklin’s fact-finding mission had put out of its misery. But the British occupation of Boston, which turned into a patriot siege of the city after the Pyrrhic victory of the British at Bunker Hill in June 1775, ended with liberation of the city by the Continental Army in March 1776. In late June 1776, yet another miraculous patriot victory turned the British back from Charleston.
The Continental Army, which on the day of Bunker Hill had consisted solely of General George Washington, steadily expanded with the incorporation of militias and the optimistic recruiting that characterizes war in its early stages. Its hopes were high. But everyone knew that the British weren’t done. In light of the limited available British manpower, George III began seriously recruiting German mercenaries (known as Hessians because most came from Hesse-Kassel). Once they arrived, another blow would fall, and it wouldn’t be long.
The Strategic Situation
Thwarted in the leading ports of both New England and the South, the most obvious place for Britain to strike next was a major port in the center of the country. While the capital in Philadelphia was a tempting target, an upriver expedition would logically follow after securing a large oceangoing port. That meant New York, with its deep natural harbor, central location, and links by river to Canada. If Britain could control the Hudson River and the line by which it connected Manhattan to Canada — as it attempted to do in the Saratoga campaign of 1777 — it could cut the new nation in half.
New York in 1776 was not yet the nation’s largest city, with only about 25,000 people compared with the 40,000 or so in Philadelphia. Lower Manhattan was heavily urbanized, but there was still a good deal of forest and farmland covering the rest of the island, and the city didn’t then include the other four boroughs. Brooklyn wasn’t incorporated as its own municipality until 1816. In 1776, it was still just another Long Island farming village surrounded by countryside.
Once captured, New York would be easy to hold — indeed, the Continental Army would never try to retake it, and it was the last place evacuated by the British in 1783. Boston could be surrounded by land on three sides, but Manhattan is separated by a narrow channel from the mainland of the Bronx to the north, and by much wider ones from Long Island to the east and New Jersey and Staten Island to the west. It would be an almost impossible spot to besiege with an 18th century army and navy, especially into the teeth of British supremacy at sea.
Taking New York accorded not only with the strategic situation but with the traditional British way of war, which dated back to the Middle Ages. The habits of an island nation with a strong navy but small standing armies formed British military thinking. With the single exception of the Duke of Marlborough in the early 1700s, British commanders who led their men far inland usually met disaster (such as with the annihilation of the British army sent to Afghanistan in 1841). Instead, Richard I (the Lion-Hearted), perhaps the greatest military commander of medieval Europe, refined a style of warfare in the twelfth century in which he hugged the coastline as closely as possible, refusing to go inland until and unless he had built a fortified line connecting him to his navy — ensuring him both a line of supply and communications and an avenue for retreat by sea. That cautious approach deterred him from marching on Jerusalem in the Third Crusade even with a superior force. Three decades after 1776, Wellington perfected the modus operandi of Richard I, remaining tethered by a fortified line to the Royal Navy both in India and on the Iberian Peninsula.
In light of the long British supply lines across the Atlantic in the Age of Sail, it is not surprising that the capture of ports as strongpoints and a hesitancy to campaign inland characterized the operations of British commanders in the American Revolution. Indeed, the war was ultimately lost when Lord Cornwallis was separated from his navy at Yorktown.
Cat and Mouse
George Washington and Congress both expected the British to hit New York; if anything, after General William Howe evacuated Boston in March, the Americans were surprised how long it took. Washington sent General Charles Lee ahead to begin organizing New York’s defenses in January, while the siege of Boston was still ongoing. After Lee was dispatched by Congress to South Carolina in March, the role fell to General William Alexander (Lord Stirling), the wealthy scion of Scottish earls. Washington himself arrived in April.
Washington proceeded to make a series of major mistakes, his worst of the war. First, in contrast to the Fabian strategy of retreat and hit-and-run attacks that characterized American strategy after the bitter lesson of Long Island, Washington committed the bulk of the Continental Army — some 20,000 men — to defend a single city. This deferred to the demands of Congress, which was perhaps overconfident after Boston and Charleston that the British could be kept from gaining a foothold. In that sense, both Washington and Congress made the same mistake as Robert E. Lee and other Confederate strategists of letting civilian political demands tie an outnumbered army to defending ground. That is partly the cost of democratic political oversight, but the difference was that early failure led Washington to learn his lesson in time to change strategy; the Confederates let their early victories in Virginia commit them to a losing approach.
Second, Charles Lee devised a defensive system to sink large ships in the harbors to block the British, and to fortify street defenses inside Manhattan in order to turn it into a Stalingrad-style labyrinth of urban combat. But here, again, Washington yielded to the fears of New York merchants that Lee’s strategy would destroy the city, while the British were already proving that they could sail past his sea obstacles. The urban warfare approach was abandoned. Washington compounded the incoherence of his defenses by dispersing his forces to defend multiple landing points on Manhattan, Long Island, and Staten Island, and by sending away cavalry units that would be useless in street-to-street fighting but essential in the sort of battle he was actually preparing to fight. Alexander Hamilton wrote an anonymous letter to his commander trying to persuade him that Brooklyn was indefensible, but to no avail.
Washington also still believed — and Saratoga would confirm that he was right — that the patriots needed to prove themselves in battle against the British before the French would get involved. But New York City was the wrong place, as it could scarcely have been more favorable to the British. Worse, something like half of Washington’s army was sick that oppressively hot summer, including the indispensable General Nathanael Greene. While the Battle of Long Island would feature the largest army Washington commanded for the duration of the war, its actual fighting strength was far less than it looked on paper.
In the meantime, Howe had been active in Nova Scotia gathering reinforcements — determined not to be undermanned again. The British armada was sighted by July 1 and soon took control of Staten Island. With 130 ships and 30,000 men, it would be the largest British expeditionary force assembled before the First World War. One Pennsylvania soldier described the sight of the flotilla: “I thought all London was afloat.” A month was then wasted in British efforts, ordered by their own over-optimistic political leaders in London, to use the threat of this armada to get Americans to accept a negotiated peace. By the time the Hessians arrived to bring the British force to full strength, it was mid-August.
Disaster
Portending trouble, a massive thunderstorm covered New York on August 21, killing at least a dozen American soldiers in lightning strikes. Washington still wasn’t sure where the British would move, even after Howe landed 15,000 men under Cornwallis in Brooklyn on August 22. Washington still thought it was a feint. In fact, General Henry Clinton — the most aggressive of the British generals — had devised yet another of his clever schemes for outflanking the enemy. Howe had overruled Clinton’s ideas at Bunker Hill, and Clinton’s flanking strategy had blown up in his face in Charleston. But this time, it would work.
General Israel Putnam, one of the heroes of Bunker Hill, was put in charge of a few thousand Continentals on Long Island on the eve of battle, replacing General John Sullivan (who stayed on in a subordinate role). Putnam felt at home with his men manning the heights facing the British, but he didn’t know the land, most of his troops were green, he had no cavalry to scout the enemy’s positions, and the hilly and forested terrain impeded communications.
When the British storm broke on the morning of August 27, the outnumbered Americans acquitted themselves well. What became known as “Battle Hill,” the most elevated point in all of what is now Brooklyn, looked to the Americans like the best place to make a stand, but they hadn’t occupied it in advance. It took two tries to wrest control of the hill from the British, who then made three attempts to recapture it. It was the fiercest fighting of the battle. Sullivan’s command, meanwhile, was holding the Guan (or Gowanus) Heights in the center of the battlefield against Hessian assaults that became notorious for bayoneting the American wounded. Sullivan’s position was overrun, and he was captured, although not before most of his force was able to get away.
Washington, realizing now that the real battle was on Long Island, arrived on the scene around 9 a.m. and poured more troops from Manhattan into the battle — perhaps a necessary relief force with so many of his men already committed, but only exacerbating the later problem of retrieval.
What the Americans learned too late was the trap Clinton had laid for them. Marching 10,000 men through the night, he had come through Jamaica Pass, one of three passes through the heights, and emerged mid-morning to flank the Continental forces. Between the lack of cavalry and Putnam’s unfamiliarity with the terrain, nobody had seen this coming. The emergence of a much larger, unexpected force was profoundly demoralizing.
Now, it was a retreat. But a retreat in good order requires someone to cover it. On the American right, Stirling and Major Mordecai Gist led a force of little more than 250 Marylanders, who earned that day the reputation of the “Old Line State” with a valiant stand in which they launched repeated attacks against a vastly larger force for hours. Washington was moved by their sacrifice: “Good God, what brave fellows I must this day lose!” Stirling himself was taken prisoner; to avoid giving in to the British, he surrendered to the Hessian commander. On the whole, some 30 Americans were killed, 800 wounded, and over 1,000 taken prisoner, with the loss of two generals keenly felt. The British lost only a few dozen men, plus a few hundred wounded.
Escape
Now, it was the turn of the chronically cautious Howe to err. With nearly 10,000 Americans huddled in redoubts, Putnam was ready to fight on as at Bunker Hill, sure that his men could extract a high cost in blood from Howe so long as his forces could shoot from behind their walls. The British could use their superior numbers to overcome that, or they could try to starve him out. Howe, not having forgotten Bunker Hill, decided to play the waiting game, counting on time to do his work at a much lower cost in blood. Clinton was furious at being restrained yet again.
Washington brought another 1,200 men in from Manhattan on the morning of August 28, gambling further on his nearly encircled position but boosting the morale of his men. Or perhaps he already knew what might follow, because the reinforcements included Colonel John Glover and his regiment from Marblehead, Mass., that included many experienced fishermen. Howe kept waiting. Meanwhile, Washington started collecting boats, which he claimed were needed to ferry in more reinforcements.
The next night, August 29, Washington held a council of war amidst another terrible storm. Late in the evening, word went out down the American lines to pack up and begin a night march for a surprise attack on the British. But that was a ruse. The army left its campfires burning behind it, and every man was instructed to keep total silence. When the men reached their destination, they found Glover and a flotilla of small boats.
This is where providence, that repeated savior of the American cause, intervened. With an almost-impenetrable fog and the wind fortuitously shifting just as the Americans needed it to — and at just the right moment — the whole army was ferried across the East River back onto Manhattan. For hours, the boats plied the river in silence in the dark. The fog still shielded the Americans after dawn broke on August 30. Washington himself, who had spent the night overseeing the evacuation on horseback, boarded the last boat. He was at his best in the crisis.
It was a miraculous, daring escape. Once again, Howe had given away a much greater victory by restraining Clinton. Washington and his army lived to fight another day, and another. They retreated north throughout Manhattan. Much of the town burned after their departure, so that all the Manhattan merchants got by avoiding urban combat was to live under British occupation for the next seven years (an outcome that suited some in the Loyalist-infested city all too well). Washington wouldn’t stop until he crossed the Hudson River at Peekskill in November, then kept running all the way into New Jersey.
Wars, as Churchill remarked after Dunkirk, are not won by retreats. Yet the American retreat from Long Island stands alongside Dunkirk and the Chosin Reservoir as one of the most inspiring and consequential retreats in history. It would be months before the American cause would see good news again. But the escape-by-night from Brooklyn kept Washington and the core of the Continental Army’s command in the field. Sometimes, just staying alive is a revolution.