Did Generals Mismanage the Battle of Brooklyn?

Critical Thinking

April 20, 2017
by Gene Procknow Also by this Author


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Outmaneuvering and overwhelming the Patriots during the 1776 Battle of Brooklyn, the British won a huge victory by executing a daring night march around the Patriots’ left flank. Patriot commander Maj. Gen. Israel Putnam is heavily criticized for not guarding a vital pass that allowed British forces to surround the advance units of the Continental Army, leading to a complete rout and mass surrender. However, the British commander, Sir William Howe, also has been heavily criticized for not following up on the victory to completely crush the remaining elements of the Continental Army. In fact, many historians believe that this was the last opportunity for the British to end the rebellion.

It is overly simplistic to focus on the Putnam and Howe “mistaken decisions” as determining the ultimate outcome of the battle. Given information available to the commanders on the 1776 battlefield, these battle strategy decisions were rational and other factors led to the Patriot defeat and to the British inability to capture Washington’s entire army. However, with the benefit of hindsight and heavily influenced by participants with military reputations to protect, historical accounts generally depict these decisions as mistakes.


In the summer of 1776, a massive British invasion fleet carrying over 30,000 soldiers assembled at the entrance of New York harbor. After the British evacuation of Boston, British commanders believed that New York City was key to their plans for reestablishing control of the thirteen colonies. Two brothers led the British forces invading New York – Gen. William Howe and Adm. Richard Howe. The Howe brothers also served as peace commissioners with an offer to pardon the rebels in exchange for ending the rebellion.

To counter this threat, Gen. George Washington moved the newly formed Continental Army to New York City from Boston. New York City, the largest city in Revolutionary America with 25,000 residents, consisted of approximately 4000 buildings on the southern tip of Manhattan. Washington had a difficult task of positioning only 20,000 soldiers in multiple strategic locations required for the defense of Manhattan. Not knowing where Howe would attack, Washington dispersed his forces to five locations in and around New York harbor. His plan was to wait until the Howe brothers committed their forces to a primary invasion objective and then concentrate Patriot forces to repel the attack.

Navigable waters surround New York City on three sides making it vulnerable to the powerful British Navy and its capabilities to land soldiers in numerous locations. To the east, across the East River from Manhattan, Brooklyn Heights lay within cannon shot of the city. Patriot generals believed that Brooklyn Heights was similarly situated to Dorchester Heights in Boston and forces that controlled Brooklyn Heights could also control New York City. First, under the direction of Maj. Gen. Charles Lee and then Maj. Gen. Nathanael Greene, Patriot troops erected extensive earthen fortifications protected by forty cannons, abatis and other obstructions.

Howe also decided that Brooklyn was key to the defense of New York City and landed his invasion force on the southern coast of Long Island, eight miles from Brooklyn Heights. As it became clear that this was the main invasion, Washington began moving forces to Brooklyn, but not nearly enough to match the size of Howe’s units.

Unguarded Pass

Patriot commanders made the first critical command decision by deploying Continental Army units to defend the pivotal Brooklyn Heights fortifications and the hills guarding their approaches. Though untested in combat, Washington selected newly promoted Maj. Gen. Nathanael Greene to lead the defense of Brooklyn.  When Greene became ill, Washington named Maj. Gen. John Sullivan overall commander in Brooklyn on August 20, 1775.[1] As more troops were added to Brooklyn’s defense, the command rated the most senior major general’s leadership and Israel Putnam was named overall commander in Brooklyn on August 24. Sullivan retained command of all troops forward deployed who guarded the passes of Guana Heights, two miles east of Brooklyn Heights.[2]  Three days later the British attacked.

Many historians point to the unavailability of Greene and the appointment of less competent commanders as a major factor in the Patriot loss.[3] However at this time, both Putnam and Sullivan had more combat experience that Greene. Putnam had commanded in numerous battles during the French and Indian War and, as importantly, led combat units on terrain similar to that of the hilly, heavily forested Brooklyn. And Sullivan commanded portions of the Patriot invasion of Canada in 1775, gaining experience with British assault and infantry tactics. Although Greene became one of the best Patriot generals, he made several critical mistakes early in his career and Brooklyn would have been Greene’s first combat experience.

Two miles in front of the Brooklyn Heights fortifications, a glacial moraine called Guana Heights offered a natural defensive barrier. It was breached in only four locations through which an army could advance. Patriot commanders stationed forces at three of the passes and only a five-person patrol at the fourth pass, which was regarded as too remote to be an invasion route. Israel Putnam, who is tagged with being unfamiliar with the battlefield, is disparaged for leaving this critical pass unguarded.

Further, critics charge that the last minute command changes led to battlefield confusion as it was unclear who was in charge, and to a disastrous change in tactical battle plans for the defense of Brooklyn.[4]  Specifically, Putnam and Sullivan are blamed for not properly understanding the Brooklyn geography and for ordering a static defense versus Greene’s planned, controlled withdrawal to the most defensible Brooklyn Heights.[5]  While a change in leadership on the eve of battle is always risky, there is evidence that the American commanders agreed upon a defensive strategy and there were clear orders to stoutly defend the passes of Guana Heights. Two days before the battle, Washington specified, “The woods should be secured by abatties &c where necessary to make the enemys approach, as difficult as possible.”[6] Further, George Washington rode with Sullivan and Putnam to scout as far as Flatbush on August 26 – the day before the battle, so there had to be clarity among the three leaders.[7] Sullivan did post five officers at Jamaica Pass, so it seems that a conscious decision was made not to defend the pass, but only to post a lookout.

However, it is clear that the British commanders had better, more detailed knowledge of the terrain, expertly aided by local Loyalist guides. The British had excellent maps and Gen. Henry Clinton possessed extensive pre-war knowledge of the area gained while living with his father who was governor of New York. In addition, Washington sent away the Connecticut cavalry, the only cavalry unit in Brooklyn, so the Patriot mobile scouting abilities were greatly hampered.

Digital variation of an 1899 lithograph depicting the retreat from Long Island.

On August 27, British forces attacked the Patriot units guarding the three southern passes while marching the bulk of their army around to the northernmost Jamaica Pass. At the three southern passes, British forces were ordered to engage but not attack. Initially, Patriot commanders were pleased to hold their lines against the more formable British and Hessian units. However, this was a false sense of accomplishment as the British were simply distracting the Patriot leaders to support the bold move around the Patriot left flank by 10,000 British soldiers.  These soldiers easily captured the five Patriot riders scouting the Jamaica Pass. The British then moved to the town of Bedford in the rear of the Continental Army units guarding the other three passes. Successfully surrounding the Patriots, British forces swept the Continental Army from the battlefield, killing or capturing over 1000 men. The bulk of the Patriot forces, however, were able to retreat to Brooklyn Heights.

Criticism of Putnam and Sullivan started immediately.  Three days after the battle, Nathanael Greene intimated that if he wasn’t ill and was in charge, the battle would have had a different outcome.[8] John Adams concured and in a letter to William Tutor, the Continental Army’s Judge Advocate, blamed bad generalship by saying, “…we have suffered in our reputation for generalship in permitting the enemy to steal a march on us.”[9]  Col. Henry Knox agreed: “The ignorance of the Grounds and the not occupying the passes on the island sufficiently has been the sole and only cause of our subsequent Retreats.”  Knox went on to state that the battle’s outcome would have been different, and New York City could have been defended, if Greene was fit for duty.[10]  Many historians agree.[11]

As with any defeat, many of the participants attempted to exonerate themselves by blaming others. Col. Samuel Miles, in charge of the Patriot left flank, also blamed Putnam for not giving proper orders the day before the battle. In addition, Miles blamed Col. Wyllys for not allowing his unit to quickly counter the British move through Jamaica Pass.[12] By the time Miles did move his brigade to Jamaica Pass, the main British force had already transited and the British rear guard and baggage train captured him. Interestingly Brig. Gen. Samuel Parsons, Patriot commander between the southern two passes, blamed Miles for not doing his duty to scout and protect Jamaica Pass. Parsons’ criticisms indicate that Patriot commanders did know about Jamaica Pass but their forces were inadequate to cover the six-mile long front against all angles of the massive British attack.[13]

Blaming Putnam, Sullivan or any subordinate battlefield commander for poor tactical force positioning does not tell the whole story. The Patriots were outnumbered seven to one outside of Brooklyn Heights, with less than 3000 Patriots against 20,000 British and Hessian soldiers. It is highly likely that the British could have routed any Patriot force disposition among the four passes and also likely that they would have defeated the Patriots at the three passes without the aid of the big right hook through Jamaica Pass.

In assigning blame, most telling were the activities and reaction of Washington.

Washington visited Brooklyn each day leading up to the battle and was present on Brooklyn Heights observing the fighting. Afterwards, Washington did not blame Putnam or Sullivan. In the end there was no genuine possibility of the Patriots holding Brooklyn. Maybe a stronger force at Jamaica Pass or better intelligence on British troop movements might have reduced Patriot casualties, but the myth that a bad decision or poor generalship lost the battle is just not plausible. Overwhelming British forces were destined to breach the Guana passes and force the Patriots back to their fortifications on Brooklyn Heights. The real mistake was the decision to defend New York City, which was indefensible given Britain’s naval superiority. The responsibility for that decision lies with the Continental Congress and George Washington.

Failure to Seize Complete victory

British Gen. William Howe made the battle’s second critical command decision after the British routed the Patriot advance forces at Guana Heights. British forces chased the remnants of the Patriot units guarding the Guana passes to within yards of the fortifications on Brooklyn Heights. Mass confusion reigned as defeated and disorganized Patriot forces entered the fortifications and mingled with the garrison. Several British commanders observed this confusion and saw an opportunity to seize Brooklyn Heights from the disorganized Patriots. However, Howe received the report of Col. Miles’ assault on the attackers’ baggage train and also a faulty intelligence report of a two to three thousand soldier Patriot force ready to attack at his rear. With the prospect of forces in his rear and the potential for more fighting, Howe decided to stop, build siege lines and force the Patriots to surrender.[14] Howe later justified his decision, saying that an attack “would have been inconsiderate and even criminal.  The loss of 1000 or perhaps 1500 British troops, in carrying these lines, would have been ill repaid by double that number of the enemy.”[15]

When the Patriots slipped away two nights later in a daring nighttime crossing to Manhattan, the decision to stop the attack on August 27 and start a siege was heavily criticized. Howe’s subordinate and frequent critic Gen. Henry Clinton “saw their confusion, might be tempted to order us to march directly forward down the road to the ferry, but which, if we succeeded, everything on the island must have been ours.”[16] Clinton went on to state how easy it would have been to seize the Brooklyn to Manhattan ferry, which would have forced the surrender of the trapped Patriot forces on Long Island. Clinton conjectured that the British could have ended the war right then and there.[17] Many historians concur that Howe stopped his troops when he had victory at hand, even had the opportunity to capture Washington.[18]

Howe is further criticized for seeking a political settlement and not vigorously enough pursuing battlefield victories. Critics conflate this event with subsequent slow reactions in the face of a weak enemy to suggest that Howe had sympathies with the Americans, suggesting that his heart was not into the battle and that he did not want to thoroughly defeat his opponents.

A more plausible reason for Howe’s halting the attack is that Howe’s troops had marched all night, fought a running daytime battle over two miles of rough terrain, and required time to rest and recover. In addition, Howe was prudently wary of another pyrrhic Bunker Hill victory. And Howe knew that the Patriot fortifications on Brooklyn Heights were built over a several month period and were much stronger than the hastily built, one evening fortifications on Bunker Hill.[19] Never again did the British launch a frontal assault against a fortified Patriot position, as British commanders could not afford to lose valuable officers and soldiers that were not easily replaced.

Howe made the right decision given the facts at his disposal. He was tightening a noose around the Patriots with the British Navy bombarding from the East River, and he was bringing up his heavy artillery to assault the Patriot fortified lines. Lastly, a Patriot surrender, especially one snaring Washington, would do more to defeat the rebellion than a battlefield victory.

In the end, it was not a battlefield decision but the weather that prevented a total British victory. Southerly winds kept the British warships out of the East River and hard rains for two days gave Washington time to reconsider his options. A dense, but fortunate fog two nights later covered the Patriots’ well-executed withdrawal to Manhattan.


Losing sides need scapegoats and excuses. If the Americans had a strategic commander who properly scouted the terrain, they would have been able to hold their lines and defend Brooklyn. If Howe had properly followed up on his victory, the British would have crushed the rebellion in its infancy. As we have seen, the commanders’ actions in each of these two critical command situations were rational given the “moment in time” decision factors including resources, geography, political considerations and risks.

Two strategic factors determined the outcome: the British outnumbered the Patriots and their navy controlled the waters. These factors decided the battle’s outcome, not tactical battlefield decisions. These same factors led to the British 1780 victory at Charleston and the American victory at Yorktown.  Second guessing a tactical battlefield decision is a well-worn tradition, but in the case of the Battle of Brooklyn, it does not lead to a different strategic outcome.


[1] William S. Baker, Itinerary of George Washington from June 15,1775 to December 23, 1783 (Philadelphia: J. B. Lippincott Company, 1892), 47.

[2] Ibid., 48.

[3] David G. McCullough, 1776 (New York: Simon & Schuster, 2005), 153–161.

[4] George C. Daughan, Revolution on the Hudson: New York City and the Hudson River Valley in the American War of Independence, First edition (New York: W. W. Norton & Company, 2016), 66.

[5] John J. Gallagher, The Battle of Brooklyn, 1776 (New York: Sarpedon, 1995), 59–60.

[6] Orders to Major General Israel Putnam, August 15, 1776, Founders Online, National Archives, http://founders.archives.gov/documents/Washington/03-06-02-0113 (original source: The Papers of George Washington, Revolutionary War Series, Vol. 6, 13 August 1776 – 20 October 1776, Ed. Philander D. Chase and Frank E. Grizzard, Jr. (Charlottesville: University Press of Virginia, 1994), 126–128).

[7] Baker, Itinerary of George Washington, 48.

[8] Richard K Showman, Margaret Cobb, and Robert E. McCarthy, eds., The Papers of Nathanael Greene, vol. I (Chapel Hill: The University of North Carolina Press, 1976), 291.

[9] John Adams, The Works of John Adams, Second President of the United States, ed. Charles Francis Adams, First, vol. IX (Boston: Little, Brown and Company, 1854), 437.

[10] Henry Knox to John Adams, September 25, 1776, Founders Online, National Archives, http://founders.archives.gov/documents/Adams/06-05-02-0021 (original source: The Adams Papers, Papers of John Adams, Vol. 5, August 1776 – March 1778, Ed. Robert J. Taylor (Cambridge, MA: Harvard University Press, 2006), 40–42).

[11] For example, see Linda Davis Reno, Maryland 400 in the Battle of Long Island, 1776 (Jefferson: Mcfarland, 2014), 18–9.

[12] Samuel Miles, “Diary” (New York, November 17, 1776), Manuscript Reading Room, Library of Congress.

[13] Samuel Holden Parsons to John Adams, October 8, 1776, Founders Online, National Archives, http://founders.archives.gov/documents/Adams/06-05-02-0025 (original source: The Adams Papers, 47–50).

[14] Gallagher, The Battle of Brooklyn, 1776, 139.

[15] William Howe, The Narrative of Lieut. Gen. Sir William Howe, in a Committee of the House of Commons, on the 29th of April 1779, Relative to His Late Command of the King’s Troops in North America:  To Which Are Added, Some Observations upon a Pamphlet, Entitled Letters to a Nobleman (London: H. Baldwin, 1781), 5.

[16] Henry Clinton, The American Rebellion Sir Henry Clinton’s Narrative of His Campaigns, 1775-1782 with an Appendix of Original Documents, ed. William D Wilcox (New Haven: Yale University Press, 1954), 43.

[17] Ibid., 44.

[18] For example, see Barnet Schecter, The Battle for New York: The City at the Heart of the American Revolution (New York: Walker & Co, 2002), 154.

[19] Gallagher, The Battle of Brooklyn, 1776, 140.


  • I’ve read little on this action but, based on what I have absorbed, I agree with Mr. Procknow’s conclusions.

    I would add one comment for each side. For the American’s, it bothers me that the party sent to keep watch on Jamaica pass to the left failed so miserably in their duty. I suspect they had no idea how to properly perform their assignment. If only one of them had got away rather than being captured–and the American commanders believed a report on the flanking move–then the American line would have been able to retire in some order.

    For the British, I can imagine that force had become rather disorganized, tired, cold, and hungry by the time they reached the American fortifications on Brooklyn Heights. Howe had learned his lesson well–that the Americans fought ferociously from behind fortifications. Another consideration that Mr. Procknow did not mention must have had some influence on Howe–that there had been pockets of stiff American resistance earlier in the day. If these two factors came together during a rather spur-of-the-moment frontal attack up hill against strong fortifications then it’s Bunker Hill again but on a much larger scale as Mr. Procknow suggests.

    1. Mike, thank you for your two additions which further support the conclusion that the battlefield commanders made the best decisions given the information they possessed in the moment. Even with our modern technology, command and control over such a large battlefield and a large number of dispersed units is difficult let alone in the 18th century. In addition, we know the outcome. The battlefield commanders did not and had to consider many scenarios, some of which might threaten their commands.

  • Good observation about the what-if-just-one-got-away scenario, Mike. It’s happened many times in military history.

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