Search This Blog

Thursday, September 27, 2018

Austin Roe: The Tale of the Mayday Messenger

Copyright ©2108. All rights reserved by the author.

Our story begins in late April 1790.  A former general and spymaster par excellence is traveling a dusty and remote country road, that leads through the sparsely settled Long Island wilderness, to a small seaside fishing village called Setauket. The former military man and espionage leader was the highest-ranking officer in the Continental Army. He travels with a small retinue of armed soldiers and cavalry officers. No harm must come to the first President of the newly formed United States of America.  For should any peril befall George Washington, political and social unrest (of the worst and most violent sort) would certainly ensue. As the chief magistrate of his government, President Washington is too important to his nation and his people to let go into enemy hands.  

Washington need not worry. He is trotting through lower New York State in a well-protected coach, and an army of belligerent foreigners no longer occupies the territory where he is moving about. The arduous and nasty war he fought to evacuate his British opponents is over and Washington and his fellow Americans are the unquestioned victors.  Even if hostile, unknown agents were around the Island, to hurt Washington, the former general is amongst the most cunning and mentally sharp men ever to have lived... hence British Major George Beckwith’s comment, “Washington did not really outfight the British, he simply outspied us!” (Kilmeade and Yaeger, 216). The President was called by his spies in the fieldAgent 711 (Rose, 121) and the ever-cautious Commander-in-Chief refuses to be separated from his mission. The Virginian’s steel-willed disposition prevents him from being deterred, no matter what his circumstances are.

But though the American President is engaged in serious business, his business is not of a military nature. “Washington made a tour of Long Island to meet the people and to examine the damage done to land and property during the British occupation,” (Kilmeade and Yaeger, 205). Washington had arrived in town also to visit the anonymous members of his secret Culper Spy Ring, and to pay the Ring’s constituents tribute (Kilmeade and Yaeger, 205) for their intrepid and faithful service.  “…on April 22, 1790, “ (Kilmeade and Yaeger, 206) Washington knocked on tavern keeper and Culper Spy Ring courier Austin Roe’s front door to spend “…a night…,” (Rose, 277) which he (Washington) “…found tolerably decent with obliging people in it,” (Rose, 277). Roe was in such a state of enthusiasm to see Washington that “…he fell off his horse and broke his leg,” (Rose, 277).

Washington’s meeting with Roe and other members of his Culper Spy Ring is one of the Spy Ring’s greatest mysteries because Washington never mentioned the encounter’s exact nature in any of his journals (Kilmeade and Yaeger, 206). Whether or not some participants of the Culper Ring were there, while others were not, historians and posterity will never know for sure. Colonel Benjamin Tallmadge, Washington’s head of military intelligence during the Revolution and lead spy for the Culpers, omits Washington’s gathering at Setauket altogether in his factually thorough and superbly written Memoir.  It is also noteworthy that none of the other Culper spies, including Abraham Woodhull, Anna Smith Strong and Caleb Brewster (as well Robert Townsend) ever decided on leaving any written accounts of their fortuitous rendezvous with their Commander-in-Chief.

Yet we, as competent students of history, are left only to speculate as to what precisely occurred at Austin Roe’s tavern on the night of April 22. After all, George Washington did spend one night there…did any prospect of Culper ever surface in the President’s conversations with his fellow Setauket spies? The odds are that it definitely did. Washington, in visiting the very hometown and base of operations of the prevailing majority of Culper’s players (Tallmadge, Woodhull, Brewster, Roe and Strong) was doing something historically more pertinent than just greeting Brookhaven Town’s general populace or congratulating “Captain” Roe (then a member of Suffolk County’s and New York State’s militia) on the fine furnishings taking up space at his inn. 

We can be very confident that the countless trees, shrubs and grasses that abound everywhere on Long Island were just then bursting forth with springtime greenery.  If Caleb Brewster and Benjamin Tallmadge both crossed Long Island Sound, south from Connecticut, to Suffolk County and the Island’s north shore, there is no record. All the Culpers had celebrated their American victory over the British back in early December of 1783, shortly after the British forces departed from New York City on November 25 of the same year (Tallmadge, 62-65). Yet, on this very singular April 22 congregation of friends, we (as readers and scrutinizers of history) should not blind ourselves to the very possible actualities of this event…despite a partial absence of evidence. For the two former Culper spies and transplanted Connecticut residents (Tallmadge and Brewster) to have both left their New England homes to step ashore at Setauket, would not have been a bother for any of them. This is so, especially because of Connecticut’s close geographic proximity to Long Island: but there are other reasons.

Culper was such an expensive enterprise for Washington and the U. S. Government to fund that, “Over the course of the War, Washington spent about 1,982 pounds on gaining secret intelligence; that fully a quarter of his budget was devoted to the Culper Ring testifies to its importance,” (Rose, 264). Culper was (in all truth) an effective instrument for the Americans to use in ousting the British military machine from their homeland…and, hence for advancing U. S. public interests. Culper’s secrecy, which was never critically violated, (Brewster could be viewed as its weakest link) was one of two principal reasons for its immense success. The other prime factor was Culper’s superbly loyal and dependable members. Washington could unquestionably lean on them all with him not stumbling over to get his goals accomplished.

For all the Culpers to converge in the presence of Washington (for the one and only time) to celebrate their astonishing and total success at the expense of British failure was not an engagement to be missed. Aside from Brewster and Tallmadge, the Culper Ring’s members were already where they needed to be to join in the celebration.  What would it mean for Washington and Austin Roe to dismiss the Spy Ring’s non-members, in order to secure privacy?  Not much. It was Roe’s tavern after all, and with Brewster and Tallmadge likely on hand to rid the scene of any possible interlopers, it would not have required any great effort.  Both men were still young enough and adequately skilled in the arts of fighting to sufficiently remove whatever unwanted parties, that may have been present, from Roe’s home and place of business. 

Austin Roe’s role in the Culper Ring was an essentially significant one. Roe was inducted into the Culper Spy Ring between late December of 1778-early January 1779 (Rose, 102) at the mutual behest of Tallmadge, Brewster and Woodhull (Rose, 102). Austin was “…born in 1749…of an old Setauket family,” (Rose, 102) and his “…jovial and spirited…” (Kilmeade and Yaeger, 56) personality made him an excellent choice to be included in the Culper Ring. Roe was easily “blended” in with the rest of the Culpers because of his consistently calm and cool demeanor. It was Roe’s distinctly pleasant disposition and conspicuous ability to get along with the others that prompted his being put into Culper’s corpus, and like spymate Caleb Brewster, he was loyal and trustworthy to a fault.  Roe would never betray his friends or their purpose…and being blessed with better street smarts than fellow Culper team member Jonas Hawkins, Roe would make for an effective field agent.  Never quick to panic in sketchy or fierce circumstances, Roe had no difficulty concealing his abundant lack of respect for the British and George III.  He had blatantly signed his name on Brookhaven Town’s 1775 List of Associators, along with Woodhull and Brewster, (Rose, 102). Roe assumed the role of Culper courier and “Despite initial concerns, Roe was pleased by the mission and eager to offer his service in any way he could,” (Kilmeade and Yaeger, 57). 

Austin was catalogued in Major Benjamin Tallmadge’s famed Culper codebook as Agent 724 (Rose, 121) and after September 1779, when co-messenger Jonas Hawkins, always antsy and over-cautious, ceased his activities with the Culpers, he left Austin Roe as the Spy Ring’s sole, full-time mailman (Rose, 172). On those few occasions when Roe was unable or unavailable to make the perilous fifty-five mile trip on horseback from Setauket to Manhattan (there were highwaymen and soldiers preying upon Yankees all over Long Island) to retrieve the all-too essential dispatches from Culper, Jr. (Robert Townsend) to General Washington (711) Woodhull bravely and unhesitatingly filled the job and kept the vital Culpers going (Rose, 172 and 194).

Roe’s innumerable journeys through the rustics of Long Island, westward, to New York City, were engagements of the most lethal kind. Once the American forces were driven out of New York City and Long Island in the fall of 1776, by General Lord William Howe and his redcoats, law and order on Long Island went from being a living and breathing thing, to an undeniable ghost of yesteryear.   “Instead of being treated as liberated territory, much of the island (Paumanok) became a military camp, and the sovereign’s loyal subjects placed under martial law.  Corruption became rampant among military administrators, and abuses against persons (civilians, specifically) and property, commonly perpetuated,” (Rose, 159).

Thieves, madcap Tory sympathizers and roving British patrols freely wandered Nassau and Suffolk Counties, searching for prey and plunder.   Shortly before he had left the Culper Ring in September of 1779, messenger Jonas Hawkins, also of Setauket, was aggressively searched by redcoats while doing Culper business (Rose, 172) and he narrowly missed British detection and (hence) compromising his security (Rose, 172).  Abraham Woodhull in the spring of 1779 was robbed of all his money by highwaymen while he also was busy doing Culper work (Kilmeade and Yaeger, 65) but the pickpockets had failed to do a thorough search of Woodhull’s clothes, and they carelessly missed grabbing the secret documents Abraham had on him (Kilmeade and Yaeger, 65). Woodhull was happy (although penniless) to still be alive (Kilmeade and Yaeger, 65). The British suspected a spy network was being run from Long Island and they were now turning up the heat and pressure on their Yankee enemies to find it out.

 Hawkins’ jumpy emotional state was justified. Woodhull (like Hawkins) was also chronically jittery and preoccupied.  But unlike Hawkins, Abe Woodhull never let his emotions get the better of him.  All the spies operating during Culper and the Revolution risked the gallows, including Roe. None of Washington’s spies wanted to wind up like their martyred kinsman, Nathan Hale, who gallantly risked his life in the autumn of 1776, to secure intelligence for the Continentals, but was rudely discovered by Robert Rogers, and subsequently found dead (by British hands) hanging from a tree.  The fear of all the Culpers getting caught and executed by the redcoats was a perpetual and terrifying one.  It never left their minds, but it did manage to keep all of them alive, alert and safe.

Long Island and all of the City of New York had been Washington and the Continental Army’s great blind spot, since the untimely and tragic demise of Nathan Hale.  The Culpers’ goal for Washington had always been for them to see through the British miasma and mire that surrounded NYC and Long Island, and to accurately and expeditiously report back all they witnessed to the American Commander-in-Chief. Austin Roe would make sure that the Culpers’ lines of communication would run unimpeded and in secret, especially when Culper Junior’s dispatches from Manhattan were in his (Roe’s) own grasp.

When Roe entered into the American Secret Service (a. k. a. the Culpers) the Culper Spy Ring was in a very fragile and vulnerable state.  Woodhull, Roe and Hawkins (as well as Anna Smith Strong) were unproven and inexperienced “investments,” whereas Major Tallmadge and Caleb Brewster were tried and true “assets.”  But what was unmistakable at this particular point of Culpers’ history was that the inclusion of the four novices into the Ring made the Ring work soundly. Washington was to get well-rewarded for all the Culpers’ efforts…and Austin Roe played a huge role in Culpers’ success.  Roe was never arrested or discovered by the British once during his duties with the Culper Spy Ring, and it was Roe who risked his neck many times over.

Like Caleb Brewster (also a Culper courier) Roe would incessantly jeopardize his life by exposing it to the harm of the numerous Tory and British cutthroats that victimized travelers on Long Island and New York City roads.  Similar thieves and opportunists thrived in and skulked about Long Island waters and coves (especially in the Sound).  Brewster was a superbly able seaman who could always dust them off (and when that did not work, he simply outfought them).  And Roe, like Brewster, was not easily bullied or ensnared. 

Tavern-keeper Austin Roe was truly a well-placed resource. Major Benjamin Tallmadge and Culper cell-leader Abraham Woodhull sagely chose Roe as an ally in their shadowy and clandestine efforts to thwart the British military initiative, early on. Unlike, Woodhull, whose repeated trips from Setauket, Long Island to Manhattan Island, would draw too much suspicion from redcoat soldiers (Woodhull was a farmer, who did not require extended sojourns to New York City to sell his produce) Roe, on the other hand, was a different sort of merchant. Roe’s hotel business did in fact necessitate many sequential excursions to NYC for him to purchase the supplies he needed to run his tavern.  Roe was thus an ideal postman for Culper selection. Any attention Roe attracted to himself would be passed off by British authorities as principally innocuous and unimportant. Culper letters and communications would consistently be in safe hands while going along their circuits from point A (Manhattan) to point B (Setauket) and from there, to point C (Connecticut, and also Brewster’s leg of the Culper route).  Brewster and Tallmadge then would have a dragoon officer (at General Washington’s behest) express ride all Culper dispatches directly to the Commander-in-Chief (Rose, 102).  Agent 711 (and his camp) was therefore the terminus of the Culper communication route (and point D).

Austin Roe was given money by Anna Smith Strong, also of Setauket, to purchase various pricy goods for the Long Island matriarch, goods that Mrs. Strong would not be able to buy for herself (Tyler, 4). This then gave Roe an additional impetus to go into “York Island,” for doing his message pick-ups (Tyler, 4). So Austin’s cover story was never simplyjust a cover story…it was one habitually supported by fact.  Mr. Roe would hence have less to worry about than Abe Woodhull, whose reasons for traveling into Manhattan (from Suffolk County) were very limited. 

Roe’s espionage efforts were mainly confined to message transports. Culper Senior (Abe Woodhull) in Setauket and Culper Junior (Robert Townsend) at Manhattan filled the roles of secret observers better than did Agent 724.  Washington and Ben Tallmadge required more than simply sharp minds and sharp eyes prying about enemy camps…they needed two men who could see even more keenly beneath any British veneer of military circumstance than a good man like Roe could. Woodhull and Townsend accomplished these tasks perfectly…but unlike them both…(as a spy) Austin Roe had the proverbial “nerves of steel.” 

Austin Roe’s story is one that is still being written.  In the fall of 2015, Long Island historians came across a letter written by one Nehemiah Marks, a Tory sympathizer and Loyalist soldier (Leuzzi, 1).  The letter was written during the Revolution and was discovered by film maker Mark Sternberg, who then forwarded it to Village of Port Jefferson Mayor Margot Garant (Leuzzi, 2).  Garant and Long Island historian Georgette Grier-Key designed and promoted a public exhibit at Port Jefferson, to celebrate the letter’s historical significance.

Marks addressed his letter to then Head of British Army Intelligence Major Oliver De Lancey (Leuzzi, 1) who was Major John Andre’s successor in that position. In the letter, Marks accuses Roe family members at Drowned Meadow (Port Jefferson) Nathaniel Roe and Phillips Roe of providing aid (intelligence and supplies) to Culper spy Caleb Brewster (Leuzzi, 1). The letter is important because it connotes actual historical suspicions on Austin Roe’s family being involved in anti-British activities, and that the British were fully aware that Washington was operating a spy ring on Long Island.

But it should be noted that the letter is not conclusive evidence that the Culpers used Roe’s family as operatives or anything else.  For if the British were certain of the Roes of Drowned Meadow helping the Culpers in any way, Nathaniel and Phillips Roe would have been promptly captured, arrested and executed by King George III’s authorities and hung from trees as enemy agents.  Nathaniel and Phillips Roe evaded detection of any alleged spycraft and escaped British scrutiny successfully.  Nathaniel Roe died in 1789 and was the first cousin of Austin Roe.

That Roe recruited his family to assist in Culper activities is very far from the impossible, for it was Roe who inducted Jonas Hawkins into the Spy Ring in 1778 (Kilmeade and Yaeger, 60). By Austin reaching out to his trusted and valuable family members to ensure the Culper Spy Ring’s success only further adds esteem to Roe in terms of his diligence and reliability to Culper’s framework and purpose.  Austin functioned in a world where he was not going to be intimidated by anyone. Yet, there is nothing in the Roe family archives (as yet known to historians) to definitively to reinforce this strictly hypothetical link. To rule its validity totally out would be both academically premature and historically unthorough. Historians should view the Marks letter as vital circumstantial evidence establishing a connection from Roe’s extended family to facilitating his Culper allies Brewster and Tallmadge.  More on this topic is likely to surface from further historical research.

Although Roe did occasionally add to Culper intelligence reports (Rose, 132) he was principally a very effective and valued Culper courier.  It was Roe who had brought back news (via Samuel Culper Junior) that the British Navy was planning an ambush of the French fleet’s intended anchoring at Rhode Island in July, 1780 (Kilmeade and Yaeger, 123). Abraham Woodhull (knowing the great significance of Roe’s dispatch) marked out Major (and soon to be Colonel) Tallmadge’s name, and promptly turned the message over to Caleb Brewster.  Brewster then expedited its delivery directly to Colonel Alexander Hamilton, via an unnamed dragoon officer, who road at breakneck speed to Washington’s headquarters, giving the very pertinent papers to the great General (Rose, 190-191).

Washington, after careful ruminating on the matter, then acted on it. Agent 711 swiftly called together a council of war and he decided to give up on a much-wanted assault on Manhattan, in favor of staging a better, much more productive ruse against the British (Kilmeade and Yaeger, 124-125).  Washington instantly wrote up phony American battle plans to seize New York City and he had a secret aid of his quickly and nonchalantly leave them behind enemy lines. British forces rapidly discovered the counterfeit U. S. attack schemes, and, thinking them valid, made no haste in turning them over to the British Army’s high command (Kilmeade and Yaeger, 125). British General (and Commander-in-Chief) Henry Clinton’s aids recalled him to NYC, to prepare for Washington’s reputed onslaught upon the redcoats (Kilmeade and Yaeger, 125). 

Clinton was in an armed flotilla and sea-bound for Rhode Island (Newport, specifically), to attack Count Rochambeau’s fleet, which was landing six thousand French troops there (Kilmeade and Yaeger, 125). Seeing British signal flares from Manhattan light up the sky, General Clinton recalled his attack force to New York County, to muster an effective counter-offensive versus the Yankees, who were never to come or to show themselves (Kilmeade and Yaeger, 125-126).  Rochambeau’s forces safely evacuated their boats and set foot on American shores…Washington’s ploy against the British had worked well, indeed, and the United States now had a very powerful military friend to aid them in their epic plight to trounce King George III’s army, from the thirteen colonies (Kilmeade and Yaeger, 126).  Austin Roe and the rest of the Culpers gave the Continentals and Washington the necessary momentum the Americans needed to bring the French into the Revolution, without casualties of any kind.  The Culper Spy Ring may have had its finest hour, here, during this particular point in time.  

Austin Roe, after the American Rebellion against Great Britain concluded in the autumn of 1783, resumed the operating of his Setauket tavern. Gone were the despised presences of annoying Tories or the insatiable and cutthroat redcoats, who both had stayed in Setauket (unwelcomed) during the War for Independence. Six and a half years later came his highly esteemed meeting with Washington.  In 1798, Roe moved his wife and eight children to Patchogue, on Long Island’s south shore, where he opened another hotel, and prospered even further (Kilmeade and Yaeger, 211).

Roe was said to tell his guests (unlike the other Culpers) of his Revolutionary espionage activities…but with very careful forethought, so as not to bring harm upon them (Kilmeade and Yeager, 211).  Roe became a captain in the Suffolk County militia in 1787, in the same year when the American Constitution was created and adopted (Rose, 277). He lived a full and enduring life, dying at his south shore home in 1830, at eighty-one years of age (Rose, 277).  Roe was then one of Suffolk County’s most prominent citizens, and his many descendants flourished after his death, through the nineteenth century, till the present day.  

The Roe’s are justifiably very proud of their great forebear, Austin. It was Roe who gathered insurmountable courage, when many of his American neighbors were inexplicably sympathizing with the enemy English, or, (even more oddly) when still others became apathetic to both sides.  Austin Roe was an authentic patriot, who lived his life as he had sought to live it…in his own way and by his own toil.  Willing to risk his life at every twist and turn of a Long Island road or of a New York City street, to advance individual freedom and universal liberty, Austin did just that.  What footpaths would you walk over or what grounds would you cover, to gain such a trophy?  

About the Poet: Michael Mauro DeBonis is a poet and a historian from Long Island, NY. A graduate of both SUNY Stony Brook (B.A. English) and Suffolk County Community College, Mr. DeBonis’ first work appeared in The Village Beacon Record and The Brookhaven Times Newspapers. Michael’s latest work (poetry and prose) may be found in the About the Author: Michael Mauro DeBonis is a poet and a historian from Long Island, NY. A graduate of both SUNY Stony Brook (B.A. English) and Suffolk County Community College, Mr. DeBonis’ first work appeared in The Village Beacon Record and The Brookhaven Times Newspapers. Michael’s latest work (poetry and prose) may be found in the New York History Review and The New York History Blog (prose only). Mr. DeBonis is dedicated to studying and to learning the history of the great State of New York. and The New York History Blog (prose only). Mr. DeBonis is dedicated to studying and to learning the history of the great State of New York.


1)   Michael Mauro DeBonis.  Long Island Surnames.Com, genealogical probing of Austin Roe’s family in Brookhaven, NY, on November 3rd, 2017.

2)   Brian Kilmeade and Don Yaeger.  George Washington’s Secret Six.  New York, NY: Sentinel and Penguin Books, 2013-2014.

3)   Linda Leuzzi. “A Letter of Significance,” The Long Island Advance: Patchogue, NY (October 22nd,2015).

4)   Alexander Rose. Washington’s Spies.  New York, NY: Bantam Books, 2006.

5)   Beverly Tyler. “A Case for Anna Smith Strong: Her Relationship with the Setauket-Based Culper Spy Ring,” The Historian, vol. 52, Issue 1, East Setauket, NY, Winter 2015. 

No comments:

Post a Comment