The Fate of the Fifth Company

As mentioned in my last post, I am researching the lives of soldiers who fought in the Fifth Company at the Battle of Brooklyn. We have several accounts of the battle by members of the Fifth Company and other members of the Maryland Regiment. These accounts contain vivid descriptions of the retreat at the battle, which gives invaluable insight into the challenges faced by the heroic soldiers of the Maryland 400.

A mixture of inaccurate intelligence reports, a misjudgment of British troop strength, and ineffective troop deployment in preparation for the Battle of Brooklyn proved almost fatal for the entire Continental Army. At three o’clock in the morning on August 27, 1776, the British attack began with a frontal assault in which the Marylanders engaged in “a pretty severe fight with Jagers [Hessians].”[1] Following this initial act of aggression, the frontal assault by the British came to a halt, giving a sense of relief to the American troops.

“A plan of New York Island, with part of Long Island, Staten Island & east New Jersey, with a particular description of the engagement on the woody heights of Long Island, between Flatbush and Brooklyn, on the 27th of August 1776 between His Majesty’s forces commanded by General Howe and the Americans under Major General Putnam, shewing also the landing of the British Army on New-York Island, and the taking of the city of New-York &c. on the 15th of September following, with the subsequent disposition of both the armies.” William Fadden, 1776. Image from the Library of Congress, Geography and Map Division.

Their relief however, was short lived. This attack was a diversionary tactic to draw American focus away from the approaching British Army. Under the cover of darkness on the night of August 26, the British had moved 10,000 troops into position to flank the American troops using the unprotected Jamaica Road.[2] Soon after the British stopped their frontal attack, the body of the British Army flanked the American left, attacking the Continental Army in the rear. The Maryland troops positioned on the right of the American wing “were surrounded by Healanders [Highlanders] on one side, [and] Hessians on the other.”[3] Taken by surprise by the British use of “a route we never dreamed of [being used],” General John Sullivan’s line broke almost immediately.[4] Seeing this, General Stirling ordered an immediate retreat. Quickly organizing two of his best regiments, the First Maryland and Delaware Continentals, General Stirling led six successive thrusts against the advancing British troops enabling the body of the Continental Army to retreat.[5] Sustaining heavy cannon and mortar fire every “now and then taking off a head,” the men of Maryland and Delaware stood “coolly and resolutely,” while they followed orders to hold their fire until the British were within fifty yards.[6] The Marylanders fought with “more than Roman courage,” in the face of an enemy whose force far outnumbered their own.[7] Such a display of courage prompted the exclamation “Good God! What brave fellows I must this day lose!,” from General Washington who stood watching the battle unfold.[8]

Stirling’s troops held off the British advance long enough for the body of the Continental Army to successfully retreat before falling back themselves. While retreating, the Maryland Regiment, led by the Fifth Company, was ambushed by an advanced company of British troops. Out of the woods “a British officer appeared, as if alone, and waved his hat,” in apparent surrender.[9] As the Maryland troops approached, the officer “clapped his hands three times,” and an entire company rose and fired.[10] Captain Nathaniel Ramsey and Lieutenant David Plunket of the Fifth Company “were foremost within forty yards of the enemy’s muzzles,” during the ambush.[11] Neither was hit since most of the fire overshot the retreating soldiers. An anonymous soldier from the Fifth Company recounted that he “had the satisfaction of dropping one of them [a British soldier] the first fire I made.”[12] Generals Stirling and Sullivan were both taken captive as their men forced their way towards Gowanus Creek. There the companies divided.

The Third, Fourth, Sixth, Ninth, and Seventh Independent Companies temporarily drove back the British troops, giving the First, Second, Fifth, Seventh, and Eighth Companies time to wade through the swamp. Ramsey’s six foot three inch frame which made him “a fine Mark for a shot,” as far as his family was concerned, saved him from drowning while crossing the swamp.[13] Ramsey had “happened to take so deep a part [of the swamp] that he was obliged to hold up his chin to keep the water from running into his mouth.”[14] James Peale, Ramsey’s brother-in-law who also successfully escaped through the swamp, lost his shoes in the process.[15] Captain Samuel Smith of the Eighth Company led his troops through the swamp. With the help of one of his sergeants, Smith heroically “swam over and got two slabs [of wood] into the water, on the ends of which they ferried over all who could not swim.”[16] In the process of crossing the Gowanus Creek three men from the Maryland companies drowned and one was shot.[17]

The Third, Fourth, Sixth, Ninth, and Seventh Independent Companies skirted the edge of the swamp as opposed to risking drowning in the swamp.[18] Blocked from rejoining the body of the Continental Army by General Cornwallis’s troops, the remaining companies were forced to engage the enemy in one last stand at the Old Stone House and sustained severe casualties as a result. The bravery and sacrifice shown by the Maryland 400 saved the Continental Army from demolition at the Battle of Brooklyn and helped to earn Maryland the title the “Old Line State.”

[1] Letter, William McMillan to “Secretary of Treasury,” ca. October 1828, Pension of William McMillan, National Archives and Records Administration, Revolutionary War Pension and Bounty-Land Warrant Application Files, NARA M804, S 2806, 33-35.

[2] David Hackett Fischer, Washington’s Crossing (New York: Oxford University Press, 2004), 95.

[3] Pension of William McMillan, 33-35.

[4] Extract of a letter from New-York: Account of the battle on Long-Island, September 1, 1776, American Archives Online, Series 5, vol. 2, 107.

[5] Ross M. Kimmel “In Perspective: William Smallwood,” (Maryland: Smallwood Foundation, Inc., 2000), 8.

[6] Extract of a letter from New-York: Account of the battle on Long-Island, 107.

[7] Extract of a letter from New-York: Account of the battle on Long-Island, 107.

[8] Fischer, 95.

[9] “A Sketch of the Life of General Samuel Smith During the War of the Revolution,” 1834, Samuel Smith Papers, Library of Congress, Box 7, Reel 5. Maryland State Archives, Special Collections MSA SC 3958, SCM 5993-1. Published as “The Papers of General Samuel Smith. The General’s Autobiography. From the Original Manuscripts.” The Historical Magazine, 2nd Ser., Vol. VIII, no. 2, 82.

[10]Autobiography of Samuel Smith 82.

[11] Extract of a letter from New-York: Account of the battle on Long-Island, 108.

[12] Extract of a letter from New-York: Account of the battle on Long-Island, 108.

[13] Charles Willson Peale, The Autobiography of Charles Willson Peale, vol. 5 of The Selected Papers of Charles Willson Peale and His Family, ed Lillian B. Miller and Sidney Hart (New Haven and London: Yale University Press, 200), 123.

[14] Peale,123.

[15] Peale, 123.

[16] Autobiography of Samuel Smith 83.

[17] Mark Andrew Tacyn “’ To the End:’ The First Maryland Regiment and the American Revolution” (PhD diss., University of Maryland College Park, 1999), 59.

[18] Tacyn, 56.

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