The Revolutionary War spy drama “Turn” on the AMC cable TV network is a much fictionalized version of the activities of a real life American patriot, Ben Tallmadge who headed the “Culper Spy Ring” based on Long Island.
However, Westchester and the surrounding counties of Dutchess, Orange and Putnam have their own connection to Revolutionary War espionage story in the persons of John Jay, Elijah Hunter, and Enoch Crosby.
John Jay (of Bedford, NY), who later became the first Chief Justice of the United States, oversaw the activities of a New York legislative committee known as “The Committee of Safety from summer 1776 to winter 1777, It was charged with “detecting and defeating conspiracies.” The conspiracies largely were British attempts to use Tories to control New York City.
Jay’s committee made arrests, conducted trials, and used at least 10 agents including the above named operatives to gather information on British and American Loyalist operations in New York City, Westchester and surrounding Counties in the Lower Hudson Valley.
Elijah Hunter was born in 1749 in the Village of Bedford and led an eventful life, particularly during the Revolution. Early in the War Elijah Hunter, served as lieutenant and as captain of Grenadiers at the Battle of White Plains. He was also a delegate to the Assembly of Westchester. He later worked for the American side as a spy and double agent in New York City and there exists at least a dozen letters in the George Washington Papers that reference Hunter’s role as a secret agent.
One of these is Washington’s letter to Hunter in which the General attaches exaggerated information about the strength of the American forces in the lower Hudson valley area. He intended that it fall into the hands of the British and force them to keep a large force pinned down in New York City to defend the it and unavailable to assist General John Burgoyne’s forces who were marching down from Canada. In part, the letter says:
“Inclosed (sic) you will find a return of the troops fit for duty under my immediate command. For the reasons I mentioned to you the other day I have not the least objection to our real strength being known, and it will be well for you to inform that you came by the knowledge of it from inquiry and your own observations of the troops when under arms upon which you formed an average estimate of the force of each regiment in the different Brigades; to give your account, the greater air of probability you may observe that the Officers are very incautious in speaking of the strength of their regiments. “
In a follow-up letter to General Robert Howe who would later confront Burgoyne at Saratoga, NY and environs, Washington refers to Hunter as number “95” in some correspondence and as “Mr. H” in others. Of Hunter’s capacity as a double agent, Washington writes:
“…do not conceive it would be expedient in you to drop the smallest hint by which he could discover the tendency of these inquiries, much more the time and manner of execution, if these should be the result of them, considering him as a double character, [emphasis added] it is more than possible he would give some intimation by which the project would be ruined, if otherwise it bid fair for success.”
Moreover, in a letter to General Mc Dougall he states:
” I have had a good deal of conversation with Mr. H-——. He appears to be a sensible man capable of rendering important service, if he is sincerely disposed to do it. From what you say, I am led to hope he is; but nevertheless, if he is really in the confidence of the enemy, as he himself believes to be the case, it will be prudent to trust him with caution and to watch his conduct with a jealous eye. I always think it necessary to be very circumspect with double spies.”
Among the most interesting of these is an exchange between Washington and Hunter regarding the latter’s service as a spy. In one Washington wrote:
“The Recommendations given in your favor by Mr. Jay then President of Congress and Major General McDougall were such as induced me to repose great confidence in you, and to my own knowledge, after being employed in the manner abovementioned you obtained such intelligence, either by yourself or your Correspondents, of various things which passed within the British Lines, as was of considerable consequence to us. Under this recollection of circumstances I cannot hesitate to Certify, that I thought at the time and still conceive your services were of such an interesting Nature as entitled you to the good opinion and favorable Notice of your Countrymen. I am &c.’
Later on in February of 1790 the exchanges were a little tenser as Hunter sought payment for his services to the nation. He claimed “four years and 4 months pay as Captain allowed me for secret services performed by me for the United States from the first of March, 1778 to March 1st 1783 at forty dollars per month.”
Washington responded saying, in part:
“General McDougall, who, I well remember, had two hundred Guineas put into his hands, with which to pay those who were used as secret Agents, I always supposed (if more than recommending you to the State of New York, which seemed to be your great if not only object, was expected) that this money, or a part thereof, would be applied. From this view of the matter you will readily see that I cannot take any other steps in it than what have been already effected. I am etc.”
It’s not known if the matter was ever resolved, but in 1785 Elijah Hunter purchased a large plot of land in the portion of the Town of Mt. Pleasant that now comprises the Village of Ossining. Roughly, this parcel stretched from the East where Route 9 now is to the bank of the Hudson River on the West, On the North it was bounded by Main Street and on the South by the lands where Sing Sing Prison now stands. It consisted of 196 acres that was once part of the confiscated lands of Frederick Philipse and he purchased the acreage from the Commissioners of Forfeitures for £550 in gold and silver. Upon Hunter’s death in 1815, a considerable part of this land was inherited by the Baptist congregation he helped to found in 1786. Elijah Hunter is buried at Dale Cemetery in Ossining.
Enoch Crosby born in Lake Carmel in Putnam County, NY in 1750 was perhaps the best known of Jay’s agents because supposedly, he was the model for “Harvey Birch,” the protagonist in James Fennimore Cooper’s novel, “The Spy,” written while he was in residence in Scarsdale
Apparently, Jay and Cooper did discuss the exploits of Jay’s counterintelligence agents but Cooper later denied that he modeled Birch after Crosby and it appears that Birch was a composite of several agents, not Crosby alone.
Crosby, was a shoemaker and he worked for Jay from August 1776 until spring 1777. During this time he joined various Loyalist/Tory groups and gathered evidence on their pro-British activities, and then passed the information that Jay needed to have these people arrested and convicted. While infiltrating the Loyalists Crosby used aliases such as John Brown, John Smith, Levi Foster, and Jacob Brown. To cover his tracks he was invariably “arrested” by Patriot troops just as the Loyalist group was captured and then He managed to “escape” thereby keeping his Tory bone fedis intact.
Crosby also was sent on missions to identify pro-Tory groups and individuals in New York City and Vermont. However, Crosby mostly operated in the counties along the Hudson River, just north of New York City. It was a small region, with residents clustered in several villages and he was well-known in the region rather quickly. As a result, his value as a counter-intelligence agent diminished with each mission. He was in perpetual danger of being killed by the Tories were he to be discovered to be as an American agent, or harmed by unwitting Americans when captured along with Tories.
His introduction to spying came by accident when he encountered a Tory sympathizer in the vicinity of Croton Lake in Westchester while traveling to White Plains to join a Patriot military unit stationed there. For some reason the Tory assumed that Crosby was one as well and invited him to his house where he revealed the identities of other Loyalists. Crosby then passed this information to John Jay who headed the Committee of Safety also based in White Plains. Jay then dispatched a body of mounted militia to the Croton Lake area and they arrested the Loyalists. Following this operation Jay suggested that Crosby would better serve the Patriot cause as a spy, rather than as a soldier. From then on he worked for Jay by publically declaring himself as a Tory, much the disapproval of his Patriot family and friends who were not privy to hid employment by Jay
Crosby’s skillful performance as a British sympathizer impressed influential local Loyalists and he was often welcomed into their ranks. In one of these repeated instances he became a recruit in a military unit being formed among local Tories in the vicinity of Marlboro, NY in Ulster County under the direction of a British officer from New York City. The company was formed in a week’s time. Crosby soon sent the following message to Jay:
“I hasten this express to request you to order Captain Townsend’s company of Rangers to repair immediately to the barn, situated on the west side of Butter-Hill, and there to secrete themselves until we arrive, which will be tomorrow evening, probably about eleven o’clock; where, with about thirty Tories, they may find me.”
As Crosby had suggested he hid in a nearby haystack to avoid capture and when Townsend’s Rangers probed the haystack with their bayonets, he hastily gave himself up. Townsend, who supposedly was unaware of Crosby’s true loyalty, took him along with the other Tories to Fishskill, in Dutchess County and locked up in a secure room at the “Old Dutch Church.
There and as luck would have it, Crosby found that a window that somehow was not locked and he escaped The next day, his “escape” was made known to the other prisoners, and Crosby was off to join yet another Tory group and after he gathered information about them and relayed it to Jay. He was again “captured” but managed to escape thereby keeping his supposed Tory identity intact and enabling him to repeat his ruse several more times.
In 1832 he filed a deposition in a court in Putnam County, NY detailing his services as a spy for the United States in order to receive a pension and other benefits in accordance with an Act of Congress in that year. Crosby died in 1835 on his farm in Carmel, NY.