The One You Never Suspect

Experts on spycraft tell us that the best spy is the one you never suspect.  I would argue that it’s the one who never gets caught.  I asked the question, “Who were the best spies during the American Revolution?”  Among the answers provided was Nathan Hale.  He was very likely the worst spy in the history of the world.  He lasted all of fifteen minutes in his spy craft before being discovered.  Well, okay — maybe a bit longer than that.

Once the Revolution had begun in 1775, Nathan Hale joined a Connecticut militia and, within only five months, was elected first lieutenant.  The unit participated in the siege of Boston, but Hale remained behind (some suggest) because he was unsure of whether he wanted to get into the fight.  Others claim that he had a teaching contract that conflicted with his unit’s operations.  In early July Hale received an inspiring letter from his classmate Benjamin Tallmadge urging his involvement.  Within a few months, Hale had made the transition to Knowlton’s Rangers, the first “intelligence service” organized by the Americans.  After the British had defeated the Americans on Long Island, General Washington was desperate to determine the location of the imminent British invasion of Manhattan.  To that end, Washington called for a spy behind enemy lines and the man who stepped forward as the only volunteer was Nathan Hale, on 8 September 1776.

Four days later, Hale disguised himself as a Dutch school teacher and pretended to look for work.  Unfortunately, Hale carried in his possession his recent college graduation certificate with his real name inscribed — so the “assumed name” idea was quickly awash.  But while undercover, the British seized Manhattan on 15 September.  The “great New York fire erupted” on 21 September, thought to have been the work of the Americans to keep the city from falling into British hands.  Americans under Washington denied any part of the fire, but in its aftermath, British authorities detained 200 colonists for questioning.

What we know of these events was penned by a British Loyalist by the name of Consider Tiffany, a Connecticut shopkeeper.  In this account, Major Robert Rogers (Queen’s Rangers) remembered seeing Nathan Hale in a tavern and recognized him.  After luring Hale into betraying his allegiance by pretending to be a patriot himself, Rogers apprehended Hale near Flushing Bay in Queens.  Another story suggests that Nathan was betrayed by a Loyalist cousin named Samuel Hale.

The British harbored no good feelings toward spies.  They were “illegal combatants” and the punishment for spying was death.  Everyone, including Nathan Hale, knew the punishment was rather final.  At General William Howe’s headquarters in Manhattan, Hale was questioned by the provost marshal (Captain Cunningham) and most of what Hale had to say was defeated by the evidence on his person.  Hale spent the night in a bedroom in Howe’s headquarters.  It was his final night.  According to British major Frederick MacKensie, Hale “ … behaved with great composure and resolution, saying he thought it the duty of every good officer to obey any orders given to him by his commander-in-chief and desired the spectators to be at all times prepared to meet death in whatever shape it may appear.”

On the morning of 22 September, Hale was marched along the Post Road to Artillery Park — where he was hanged.  There is a question about whether Hale actually uttered the famous words credited to him, “I only regret that I have but one life to lose for my country.”  We wonder about this because there was no first-hand testimony that Hale ever said any such thing.

In any case, the 21-year-old came to his untimely end, and it didn’t take long for the British to “find him out.”  Hence, if our standard for good spies is the one who is never caught, then we must conclude that Lieutenant Hale was not a good spy.

Mrs. Ann Bates, on the other hand, had a much better career.  The British spy network included women, one of whom was Ann Bates — who may have been a near-perfect secret agent.  Recall that women in the 1770s were generally regarded as simple-minded housekeepers and baby-makers.  Bates knew this well enough to play that card as a British Loyalist.

Historians believe that Ms. Bates was born in 1748 in Pennsylvania.  She was married to Joseph Bates (a British artilleryman) and worked as a school teacher in Philadelphia.  To augment their meager income, Mrs. Bates kept bees, tended sheep, and ran a small goods store.  She was first discovered by a British spy named John Craig.  After sounding her out to determine her loyalty, Craig introduced her to his superior in New York, Major Duncan Drummond.  When General Clinton withdrew his forces from Philadelphia in 1778, Joseph and Ann Bates accompanied him.

New York City wasn’t a safe place for British loyalists.  Patriot harassment was common, along with beatings, tarring’s, and destroying personal property.  Ann Bates didn’t experience any problems with patriots in the city because she maintained a very low profile and projected someone who was simply a “typical woman.”  She was respectable, a good housewife, and insofar as her neighbors were concerned, an American patriot.  After General Clinton assigned Major John André to his intelligence staff, Ann Bates began working under his direction.  She was cool under pressure, meticulous in her duties, and clever.  Her contemporaries referred to her as Mrs. Barnes — and she was judged by historians as a great spy.  As a woman, she was able to go unnoticed through and around American army camps.  When in hiding, she disguised herself as a peddler and often frequented General Washington’s own campsites selling campsite pots and pans.

Ann Bates, whose husband was an artillerist, was familiar with field guns and thus able to provide the British with information about Continental’s weapons, their materials, and placement strategies.  One mission that she failed at achieving was the recruitment of American soldiers as British spies.  She instead began listening to the conversations of Continental soldiers and was able to glean valuable information from their grumbling and whining.  It was from a whining session among American soldiers that Bates learned about Washington’s Rhode Island campaign.

While traveling near White Plains, New York, American soldiers detained Ann Bates on unspecified suspicions but released her the next morning without any substantial interrogations.  Once she’d returned to the city, she provided her superiors with significant intelligence of Washington’s army.  Thanks to Bates’ careful observations, the British learned that General Washington’s army had far fewer field cannons than they imagined.  Bates’ boss, Duncan Drummond, was impressed with Bates’ attention to detail.

During one mission, a British deserter recognized Ann Bates for who she really was and sounded the alarm.  It was only her cool demeanor that saved her; in disguise, she moved from one British safe house to another until she could make her way back to New York City.  To get there, she traveled through New Jersey — a safe route that enabled her to stay at various Tory safe houses.  Her safe house route was similar to one utilized by escaping British POWs.  In this one instance, Bates was anxious to return to her home in the city and it may have made her a little careless.

On 26 September 1778, a Saturday, Bates was in the process of observing an American headquarters when someone noticed her and turned her in.  An officer took her to the general commanding, Charles Scott.  Scott interrogated Bates.  Ann explained that her husband was a soldier in the Center Divisions and was en route back to her home.  Eventually, Scott released Ann Bates — who doesn’t appreciate a veteran’s wife?  The episode did rattle Bates, however, and she returned to New York City as quickly as her legs would carry her.  After delivering information to Drummond, he escorted her to Long Island where she could relax and not run the risk of bumping into American soldiers.  A few days later, Drummond introduced her to an American officer — a general named Benedict Arnold.

Between October 1778 and August 1779, General Clinton’s spy network underwent important changes.  Clinton and Drummond had a substantial disagreement, Drummond refused to acquiesce to Clinton’s preferences, so, Clinton sent Drummond back to England.  General Clinton assigned Major John André to Drummond’s replacement.  Historians do not believe there was much interaction between André and Bates.

General Henry Clinton was American-born in Newfoundland. His father served as a British Admiral and the governor of Newfoundland.  These family ties may explain why General Clinton received an appointment to serve as Governor of New York.  Clinton first learned of the American rebellion while traveling with Generals Burgoyne and Howe — among whom competition was keen for the King’s favor.  Clinton’s first attempt to capture Charleston (South Carolina) ended in failure (1776), which was somewhat offset by his successes in New York and Long Island.  Clinton was subsequently advanced to Lieutenant General.

The British plan was to divide (and conquer) the American colonies.  King George III gave overall command of the northern campaign to Burgoyne (prompting Clinton to tender his resignation).  Rather than accept his resignation, King George gave Clinton a knighthood.  Ultimately, Burgoyne failed to achieve victory and Clinton replaced Howe as Commander-in-Chief of British North America.  In 1780, Clinton appointed General Cornwallis to command the southern invasion.

Joseph Bates, serving in Cornwallis’ army, traveled to Charleston with his wife Ann.  After their arrival, Ann Bates met several times with Colonel Nisbet Balfour, who asked for her assistance in setting up an espionage network in South Carolina.  Balfour, one of Cornwallis’s most trusted officers, received severe combat wounds during the Battle of Bunker Hill.  He played an active role during the battles of Elizabethtown, Brandywine, and Germantown.  Balfour was later advanced to Major General with service in France.  Despite Balfour’s intent to establish a spy network, Cornwallis abandoned the effort when he realized that nothing was going to save him from defeat at Yorktown.

On 6 March 1781, Joseph and Ann Bates sailed for England.  Ann’s participation in the war as a spy placed a strain on her marriage, prompting Joseph and Ann to separate soon after arriving back in England.  We do not know what became of Joseph, but Ann always maintained pride in her accomplishments as one of Clinton’s spies.  In 1785, Ann submitted a petition for a pension from the British government.  We know the government granted her a pension, but beyond that, there is no further record of Ann Bates.  We know she was born in 1748, and we know she was still alive in 1785 — but as with all the very best spies, there is much we never knew about Ann — or ever will. 


  1. Baker, M. A.  Spies of Revolutionary Connecticut: Benedict Arnold to Nathan Hale.  History Press, 2014.
  2. French, A.  General Gages Informers, 1932.
  3. Haywood, M. D.  Governor William Tryon and his Administration in the Province of North Carolina.  Raleigh, 1903.
  4. MacLean, M.  Ann Bates — A History of American Women.  Womenhistoryblog, 2011.
  5. McBurney, C. M.  Spies in Revolutionary Rhode Island.  South Carolina History, 2014.
  6. Nash, J. R.  Spies: A narrative encyclopedia of dirty deeds and double-dealing.  Evans & Company, 1997.
  7. Nathan, A. G. The Gentleman Spy: The True Story of the British Officer Who Might Have Presented the American Revolution.  Sedgewick & Jackson, 1970.
  8. Nelson, P.  William Tryon and the Course of Empire: A Life in British Imperial Service. University of North Carolina Press, 1990.
  9. Nagy, J. A.  Dr. Benjamin Church: Spy — A Case of Espionage on the Eve of the American Revolution, 2013.
  10. Randall, W. S.  Benedict Arnold: Patriot and Traitor.  New York: William Morrow, 1990

About Mustang

Retired Marine, historian, writer.
This entry was posted in British Colonies, British Generals, Colonial America, History, New York, Pennsylvania, Revolution, Society, Spies & such. Bookmark the permalink.

2 Responses to The One You Never Suspect

  1. Andy says:

    Interesting recount of the exploits of Ann Bates. She was certainly more successful than poor Mr. Hale, but to what end. Despite her efforts and those of other loyalist, the British failed to hang onto their interest in the New World. Still, her story is history and in that sense at least is worthy enough to be told and retold.



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