Battle of Staten Island The Battle of Staten Island was a raid by Continental Army troops under Major General John Sullivan against British forces on Staten Island on August 22 , 1777 , during the American Revolutionary War . After British Lieutenant General William Howe sailed with most of his army from New York in July , the Americans recognized that the British position on Staten Island was vulnerable , and planned an attack . Sullivan ' s raid was well - executed , but it suffered from a shortage of boats to effect the crossing , and one of its detachments was misled by its guide to the front of the enemy position rather than its rear . As a result , Sullivan did not take as many prisoners as expected , and had about 200 of his own men taken prisoner due in part to the lack of boats . Although Sullivan was accused of mismanaging the raid , a court martial held later in 1777 exonerated Sullivan of all charges . Background . In March 1776 the British forces of General William Howe withdrew from Boston after Major General George Washington fortified high ground threatening the city and its harbor . With this army augmented by reinforcements from Europe , General Howe captured New York City , forcing Washington to retreat all the way across New Jersey . At the end of 1776 , Washington crossed the Delaware River and surprised German troops at Trenton , New Jersey , and eventually regained control of most of the state . The two armies then settled into winter quarters , although there was much skirmishing before the 1777 campaign got underway . On July 23 , 1777 , following months of preparation and some preliminary maneuvers in New Jersey , General Howe and his brother , Admiral Richard Howe , launched a fleet carrying most of the New York - based army south pursuant to their plan to capture the American capital , Philadelphia , by landing the army at the upper end of Chesapeake Bay and marching north . General Washington , although he was notified promptly of the fleet ' s departure , was unaware of its destination . He heard on August 10 that the fleet appeared to be moving south of Philadelphia , possibly heading for Charleston , South Carolina . As a result , he prepared to move north to assist General Horatio Gates defend the Hudson River against Lieutenant General John Burgoyne ' s march south from Quebec . On August 21 he was alerted that the fleet had been spotted one week earlier at the mouth of Chesapeake Bay . Realizing the danger to Philadelphia , he immediately issued orders to move the entire army south with all speed . His orders to Major General John Sullivan , who commanded the front line defenses in eastern New Jersey , were to rejoin the main army " with all convenient speed " . Prelude . Sullivan , in the meantime , had learned that the departure of Howe ' s army had left Staten Island vulnerable , and planned and put into execution a raid against British targets there . He had learned that although the bulk of British regulars were near the northern end of the island , about 700 New Jersey Loyalist militia were scattered along the western shore , facing the New Jersey mainland . His plan was to cross two groups onto the island from points in Elizabethtown ( present - day Elizabeth , New Jersey ) , capture prisoners from the isolated militia outposts , and destroy supplies . They would then go to the Old Blazing Star Ferry ( between present - day Carteret , New Jersey and Rossville , Staten Island ) to return to the mainland . British defenses on the island , under the overall command of Brigadier General John Campbell , consisted of the regular army elements from the 52nd Foot , regiments of so - called " Hessians " from the German states of Waldeck and Ansbach , and the Loyalist New Jersey militia known as Skinner ' s Brigade under the command of Cortlandt Skinner . Campbell ' s men ( including the German troops ) numbered about 900 , and were stationed near the northeastern tip of the island . Skinner ' s men , numbering about 400 according to Campbell ' s report , were stationed at outposts along the western shore between Dexter ' s Ferry and Ward ' s Point . General Sullivan , at his base in Hanover , New Jersey , ordered his commanders on August 20 to prepare their troops for a march the next day . Sources do not describe the precise composition of the troops chosen , but most of them were drawn from Sullivan ' s division , which consisted of the First and Second Maryland Brigades . These brigades comprised the regiments of the Maryland Line ; additional troops chosen for the operation included companies from the 2nd Canadian Regiment and a company of New Jersey militia . On the afternoon of August 21 two columns numbering about 1 , 000 in all left the camp . One column was led by Brigadier General William Smallwood , and the other , headed by Sullivan , consisted of troops led by a French officer who had been given a Continental Army brigadier ' s commission , the Chevalier Philippe Hubert Preudhomme de Borre . After reaching Elizabethtown late that evening , they rested for a few hours , and began crossing early the next morning . One detachment , led by Colonel Matthias Ogden , crossed opposite Fresh Kills and rowed partway up the kill , in order to approach their target , the militia brigade of Elisha Lawrence , from its rear . The remaining troops crossed near Palmer ' s run on the north side of the island , where they split into three groups . Smallwood and Sullivan led most of their columns away to attack specific targets , each leaving a regiment behind to cover their line of retreat . Battle . Ogden attacked Lawrence ' s outpost at dawn , surprising and routing the militia company . After a few minutes of battle he had taken 80 prisoners , and he moved on to the outpost of Lieutenant Colonel Edward Vaughan Dongan , commanding the 3rd battalion of Skinner ' s Brigade . Dongan ' s men put up stiff resistance , even though he was felled with a mortal wound . This prompted Ogden to retreat toward the Old Blazing Star . After waiting there as long as he thought prudent , Ogden crossed his men back to the mainland before Sullivan and Smallwood arrived . Sullivan moved to attack Skinner ' s 5th battalion , under the command of Lieutenant Colonel Joseph Barton , at the New Blazing Star Ferry , but these troops were alert , and fled when Sullivan ' s forces advanced on them . Although Sullivan had placed troops to intercept men who tried to get away , many of Barton ' s men escaped , crossing over to the Jersey shore or hiding in the woods and swamps of the area . Sullivan took 40 prisoners , including Barton . Some of his men advanced on Skinner ' s headquarters , but the force there was too strong , and the Americans retreated . General Smallwood ' s column was led by its guide to the front of the Loyalist battalion of Abraham van Buskirk , instead of its rear . He ordered the attack anyway , and Buskirk ' s men fled until they were rallied by General Skinner , and the tables were then turned on the Americans . They beat a hasty retreat , although they had time to destroy camp supplies and equipment , and managed to seize a battle standard . Smallwood and Sullivan joined forces near Richmond , a village in the center of the island , and made their way to the Old Blazing Star . Sullivan sent for the boats to speed the crossing , but they never arrived , so he began crossing the troops and prisoners using the three boats that Ogden had commandeered to cross earlier . As they did this , Skinner and his company approached , accompanied by the forces of Campbell , the 52nd , and the Waldeck and Anspach regiments . Sullivan ordered the companies of Majors Stewart and Tillard to cover the retreat . Numbering roughly 80 men , they successfully held off the accumulated British forces until all other American troops had crossed to the mainland , repulsing several determined attempts to break through their line . Although some of this covering line managed to escape , a number of men were killed , and a sizable number surrendered after they ran out of ammunition and the British began firing grape shot at them . The British loss was given by the Loyalist publication " Gaine ' s Mercury " of September 1 , 1777 as 5 killed , 7 wounded and 84 missing . Sir Henry Clinton wrote that the British took 259 prisoners in the engagement , whereas historian Douglas Southall Freeman gives the number of men captured as 150 . Twenty - one of the American prisoners were officers , one of whom was wounded ; the ranking officer captured was Lieutenant Colonel Edward Antill . Aftermath . Sullivan ' s forces marched south after the battle , and were able to join Washington ' s defensive arrangements south of Philadelphia in time to participate in the key Battle of Brandywine on September 11 . General Sullivan was later subjected to a court martial over accusations that he mismanaged the expedition in a variety of ways . The court exonerated him of all charges .