A Spy Wins a Purple Heart: The Amazing Tale of Daniel Bissell and the Military Order of Merit

Background: Daniel Bissell's sketched fort on Staten Island, including the position and size of cannons. (George Washington Papers, Library of Congress). Foreground: Badge of Military Merit similar to the one awarded to Daniel Bissell (Wikimedia Commons).

On June 8th, 1783, Gen. George Washington issued the following orders to the Continental army from his headquarters in Newburgh, New York:

Serjeant Bissel of the 2d Connecticut regt. having per­formed some important services, within the immediate knowledge of the Commander in chief, in which the fidelity, perseverence, and good sense of the said serjeant Bissel were conspicuously manifested; it is therefore ordered that he be honored with the badge of merit; he will call at Head Quarters on tuesday next for the insignia and certificate to which he is hereby entitled.[1]

The badge of merit had been recently instituted; although the design inspired the Purple Heart medal, at this time it was awarded for distinguished service. “Serjeant Bissel” was the third and final recipient of this prestigious mark of recognition. Who was he and what were the “impor­tant services?”

Daniel Bissell enlisted in the spring of 1777 in Windsor, Hartford County into Capt. Abner Prior’s Company of the 5th Connecticut Regiment, commanded by Col. Philip B. Bradley. In this corps he served until the Connecticut Line was reorganized in 1781, when he became a sergeant in Col. Heman Swift’s 2nd Connecticut Regiment. On August 14 of that year he was dis­patched on a secret mission by Lt. Col. Robert Harrison, one of Washington’s aides‑de‑­camp. The mission was to pose as a deserter and gather intelligence on British military strength in New York City, presumably with a view of utilizing it in formulating an attack on the city.

The following day, Bissell arrived in New York City. To effect his mission he took the extraordinary step of immediately enlisting in a Provincial regiment of the British army. He joined the American Legion, the combined infantry and cavalry unit commanded by none other than Brig. Gen. Benedict Arnold. Bissell later ex­plained his enlistment as a measure to avoid being pressed into the Royal Navy,[2] but there is no evidence to corroborate that claim. While presses were sometimes made in the city they were usually chronicled by Maj. Frederick Mackenzie of the Adjutant General’s Department, but Mackenzie noted none at that time. Bissell may have been warned by others that he was liable to be seized should a press occur, but he also may have simply recognized that American deserters frequently joined Loyalist regiments and saw it as a relatively easy way to accomplish his task.

Bissell pointed out “that he never bore arms against America, having been confined in the hospital or employed in the Quarter Master’s depart­ment the whole time.”[3] There is no evidence of the latter, but the Legion’s muster of November, 1781 does record that he was confined in the hospital. The Legion was part of the expedition to Connecticut under General Arnold that led to the burning of New London and the storming of Fort Griswold on September 6; for Bissell not to have participated, and therefore served against his country, he must have gone into the hospital within two weeks of his enlistment or been assigned to some sort of detached duty. He served constantly thereafter with the Legion garrisoning of posts around New York City, first at Ireland Heights, then Fresh Meadows, Harlem Lane and finally being ordered to Staten Island on May 27, 1782.[4] Here he served at the Flag Staff post until deserting back to the Continen­tal Army on the night of September 26, 1782. Four others, including two sergeants, deserted from the Legion at the same time.

Upon his arrival back into the Continental Army, Bissell made a very detailed report of British troop strength and the state of their fortifications. The information would have been invaluable if an attack on New York had gone forward. However, events had long since overtaken the importance of his original mission. Almost immediately after Bissell’s entry into British lines Washington had determined against attacking New York, opting instead to concentrate his efforts against British forces in Vir­ginia. It is a mystery why Bissell waited thirteen months to return to the Americans. There were frequent desertions of British, German and Provincial soldiers from Staten Island, and indeed all the New York posts, throughout Bissell’s time with them. Yet his report states that he “fre­quently” made efforts to return, but could not until September of 1782. Regardless, his account pro­vides an interesting glimpse of intelligence gather­ing as seen through the eyes of a non-commissioned officer. Of particular interest is the level of detail given the fortifications around New York. He probably had the best knowledge of those on Staten Island, given that they were not only the freshest in his mind when he made his report and that he spent the most time around them.

Bissell’s original account is in Series 4 of the George Washington Papers at the Library of Congress. It appears below in its en­tirety.

Substance of Information given by Sergt. Bissel of the 2nd Connecticut Regt., who was sent into N.Y. for the purpose of obtaining Intelligence in the month of Augt. 1781 by Col. H—— and made his Escape from Staten Island on the 27th of Septr. 1781.

He reports, that on his arrival in the City, there being a hot press to man the Kings Ships & finding no other means to avoid it, or escape, he enter but by entering into the land Service; he enlisted in Arnolds Corps, and never has had an opportunity of getting off until Thursday last, tho he has frequently made efforts to effect it[5] – in the mean time he has exerted his utmost care & ability in obtaining information of the strength & state of the Enemy’s Force, which from his own knowledge & observation as well as the Information of others he believes to be nearly as follows viz.

                                                                             No. of men
{22nd Regt. British                     340
On Staten Island     {57   Regt. Do.                             320
{2 Compys. British Grenads.  100
{Arnold’s Corps                      125
885

NB       The strength of these Corps he knows positively from his own observation having drawn provisions & done duty with them.

                                     {7th Regt. British                      300
{37th Regt. Do.                          360
{40th Regt. Do.                         300
On York Island         {42nd (two Battalions)           600
{British Grenadiers not
{           joined their Corps       400
[6]
                                     {17th Light Dragoons              260
2220

NB       This is the most accurate account he could obtain from Sergts. & others with whom he conversed – he cannot be positive as to the 7th Regt. which has lately arrived from Savannah,[7]

{38th Regt.                               300
On Long Island           {54th Regt. Do.                        350
650
Total                                                                            3755
Deduct Arnolds                                                           125
Total British                                                                3630
[8]

Battalions of Delanceys Brigade                                 600
Skinners Brigade                                                         700
[9]
Kings American Dragoons                                         300
Pensylvania Loyalists                                                  160
[10]
Arnolds Corps                                                             125 
Total New raised Corps                                              1885
[11]

German Troops to the best of his knowledge              4000[12]
three hundred & fifty of which at Pawlis Hook

The method he took to obtain a knowledge of the strength of the several Corps, was by enquiring of the Sergts. & others with whom he was acquainted and by comparing repeatedly the force at different Posts, from the fuel Returns &c. He has also overheard Major Menzies (commandant of Arnolds Corps) say that there were about 10,000 Troops in all this Department exclu­sive of Militia, 4000 of which were Germans. He has himself very frequently upon collecting intelligence, made memorandums, & compared the several Reports together, but after Sir Guy Carletons arrival & intimation being given that any Persons being discovered to have written Information would be treated as Spies; he was forced to destroy his Papers & Estimates.

Sergt. Bissel further says, there are 24 sail of the Line now lying in New York Harbour, that they are all of them refitting or have been repaired since they came into Port. That a fleet sailed last Week, consisting of two Ships of the Line, one Frigate & twenty five Transports, said to be bound to Charles Town, to effect the evacua­tion of that Garrison.[13]

That when he left Staten Island, four Ships had just come too, against the Light House, one of which was a Prize under Jury Masts. He adds, all Vessels (Private Property or not) which have been stript of their sails, & laid up for a long time are now refitting for Sea. He believes there are more than 100 Transports in the Harbour. Notwithstanding the preparations, &* a Cer­tainty that the Heavy Artillery has been removed from the Park, as to the amount of Twenty Peices of Brass Cannon (24 & 18 Pounders) which were supposed to be put on Board Transports in the East River near the Ship Yards. Yet it is not the opinion of the Officers or Citizens in general, that New York will be evacuated until next Spring. In the mean time a number of Refugees are preparing to go to Halifax, the number is reported to be 200,[14] but he did not hear of any British that were to sail except the Officers & Non Commissd. Officers of Lord Rawdons Corps, who are to go to Ireland.[15] As to maga­zines of Fuel & Forage he observes, tho considerable, they are not sufficiently large, but that the Enemy are daily encreasing them. It is expected whenever the British abandon New York, the New Corps will be sent to Canada. Annexed is a plan of the Enemy’s works.

*This fact he knows from his own observation.

The Main fort on Staten Island is from East to West is about one Hundred & Forty feet Through and about one Hundred feet from the North Side to the South. The Intrenchmt. is About Ten feet Wide & Six Deep With a Row of pickquets[16] Set Up in the Senter of the Intrench­ment, the Tops of the piquets About Level With the Surfice of the Earth.[17] A Row of Abattis[18] about Two Rod, in front of the Intrench­ment and About one Rod Through & about Breast High.

Their is a Row of piquets all Around the Breastwork Upon the Top of the Timber Which is Level With the Ground

The fort Will Contain fifteen Hundred men the Heigth of the Breastwork is a Bout Five feet High and about 18 feet Through.

The Gate is on the South Side of the Fort Next to the Warter. The Door of the Bumproof[19] is facing that. Their is Fourteen Ambrasures[20] in the fort & Twelve Twenty four pounders Mounted in it, four pointed against the Warter Two Upon the North Side Two Upon the South Side Four Upon the West Side. If the fort was to be atacked it Would be Best Upon the South Side of it Next to the Warter by the Gate.

As you Enter the Gate Upon your Rite hand their is mounted Two Twenty four pounders Within fifthteen Rod South of the Gate their is a three Gun battery With Three Twenty four pounders.

About Twenty Rod Below that Their is a Nother Two Gun Battery With one Twenty four & one Eighteen pounder. One Nine pounder their Not mounted.

About Forty Rods below that is a Nother 3 Gun Battery With 2 Twenty Four pounders & one Thirty Two.

The Other fort Lies Southwest of the former it is four Squair With Much Such an Intrenchment[21] Picketed Abatiss With Two peses in the fort one 24 one 12 pounder. The Gait is Upon the East Side of the fort the platform the peses Stands Upon is on the West Side of the fort.

The Ditch or Coral[22] Runs in front of Byards Hill is a bout 14 Feet Wide and Ten Deep it Runs along Just in front of old fort Bunker Hill from the North River to the East River from the Top of the Hill at the East River it Runs a Long South Upon the East River Bank.

There is a Nother Coral Runs from What was Call’d Cobble Hill at Brookline along Upon the Edge of the Hill Till it Comes Down to the Water Up against the Old Ship Jersey in A Direct Line With that on York Island.

The Grand Battery at New York is of Late Ben Repair’d, it is Ben Drawn in Less Compers[23] but in the Same manner they have Now Mounted On the Grand battery In New York. Sixty Three peses of Cannon the Most part of them are Twenty Four pounders the Rest Eighteens & Nines.

 

[1] John C. Fitzpatrick, ed. The Writings of George Washington from the Original Manuscript Sources, 1745‑1799 Vol. 26 (Washington, DC: Government Printing Office, 1939), 481.

[2] Pension deposition of Daniel Bissell, US National Archives, Collection M‑804, Pensions and Bounty Land Application Files, No. W23604, Daniel Bissell (Theoda), Connecticut.

[3] Ibid.

[4] Benjamin Craven Orderly Book, Newberry Library, Vault Case MSF 8326.2.

[5] Daniel Bissell enlisted in Captain Samuel Wogan’s Company of the American Legion on August 15, 1781. He deserted from the post at the Flagstaff on Staten Island, along with four others, on September 29, 1782. National Archives of Canada, RG 8, “C” Series, Volume 1871, Page 29 & Volume 1872, 29.

[6] These were the grenadier companies for corps that were not at New York or that had been taken prisoner at Yorktown, namely, the 17th, 23rd, 33rd, 43rd, 63rd, 64th, 70th, 74th & 76th regiments of foot.

[7] The 7th Regiment had evacuated Savannah, Georgia that July. They arrived in New York with about 260 officers and men. Great Britain, The National Archives, Colonial Office, Class 5, Volume 106, 333 (hereafter cited as TNA, CO 5).

[8] The total British rank & file present and fit for duty on September 1, 1782 was actually 4,563. Some of the numbers Bissell reported exactly corresponded to the British troop return; he only neglected mentioning the very under‑strength 3rd Battalion of the 60th Regiment. TNA, CO 5/107/220‑­221.

[9] The 1st and 3rd (late 4th) Battalions, New Jersey Volunteers, commanded by Brigadier General Cortland Skinner.

[10] This was about the combined strength of both the Maryland and Pennsylvania Loyalists. These units had been taken prisoner by the Spanish in May of 1781. They arrived in New York on parole the following July and were exchanged about a year later.

[11] This number is amazingly close to the actual number of present and fit for duty on September 1, 1782: 1,846; however, there were more corps than he listed, including the Queen’s Rangers and British Legion.

[12] This was the only number in which he was significantly off, there being over 7,000 Germans present with their corps and doing duty at the time. The troops at Paulus Hook consisted primarily of a detachment of the Anhalt‑Zerbst Regiment.

[13] Charlestown, South Carolina was indeed evacuated on December 14, 1782. 126 vessels carried troops and Loyalists to New York, St. Lucia, Jamaica, England, East Florida and Nova Scotia.

[14] This was the garrison of Fort DeLancey on Bergen Point, New Jersey. The Refugees were commanded by Major Thomas Ward. 471 men, women and children embarked in early October for Digby, rather than Halifax. TNA, Headquarters Papers of the British Army in America, TNA 30/55/5663.

[15] Lord Rawdon’s corps was the Volunteers of Ireland. British General Orders for August 3, 1782 announced that the regiment in America would be drafted, with the commissioned and non‑­commissioned officers being sent to Ireland.

[16] Piquets (or pickets), poles driven into the ground and standing straight up, at close intervals.

[17] That is, the trench was six feet deep, and had a six-foot high wall of picquets in the middle of it.

[18] Abbatis, an obstruction formed by felling trees so that the branches face the enemy.

[19] Bombproof, an underground chamber covered with enough earth that mortar bombs cannot penetrate it.

[20] Embrasures, cutouts in the parapet for cannon to fire through.

[21] That is, a trench much like the one of the other fort.

[22] Bissell appears to use the word Corral to mean a ditch connecting a series of fortifications, but we have not found this term in any period military dictionary.

[23] That is, encompassing a smaller area.

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3 Comments

  • Todd, you are certainly correct that by the time Bissell returned to American lines his intelligence was of little value to Washington as negotiations were underway for the November provisional agreement for cessation of armed conflict. In my book I make the argument that Bissell’s original assignment related to Washington’s deception plan to convince Clinton that New York was the target for an American-French attack and thus not reinforce Cornwallis in the Tidewater. I also speculate that the awards had more to do with morale and the lack of funds for promotions and rewards than actual military merit.

  • Great article, Todd. Bissell was a brave guy (least of which for joining a Loyalist regiment posing as a deserter) and deserved the Purple Heart.

    It’s very lucky he didn’t get pressed after all into the British navy! We might not have ever heard from him again.

  • An intriguing aspect of this story is that hundreds of soldiers did the very same thing that Bissell did – deserted from one side, joined a regiment in the other side, deserted again some time later, and provided intelligence to the original side. Some then deserted yet again and provided intelligence to the other side – it’s a wonder how some of them kept track of which side they were on. Where Bissell stands out is that, rather than being an opportunist like most others, his explicit purpose was to gather intelligence, and the quality of the information he collected was quite good compared to that provided by most deserters.

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