Alexander Hamilton: Spymaster

To win a war against the most powerful military in the world, General George Washington employed a vast network of spies to gather intelligence and deceive the enemy with misinformation. As the commander-in-chief’s “principal and most confidential aid,” Alexander Hamilton provided Washington with indispensable assistance in developing and managing his secret service. Hamilton scholar and biographer Michael E. Newton describes how Alexander Hamilton received intelligence from his own informants and from Washington’s spies, distributed these reports to the relevant military officers and political officials, leaked misinformation to the enemy, and even acted on incoming intelligence in Washington’s absence, activities that covertly helped the United States win the American Revolution.

Presented at Fraunces Tavern Museum on July 7, 2016.

Michael E. Newton is the author of Alexander Hamilton: The Formative Years,  Angry Mobs and Founding Fathers, and The Path to Tyranny.

 

Alexander Hamilton
Spymaster
Michael E. Newton
Alexander Hamilton: The Formative Years
Hamilton’s Contributions
Washington’s “penman.”
Interrogation of prisoners and deserters.
Recruited and managed spies.
Received intelligence.
Acted upon incoming intelligence.
Counterintelligence.
Washington’s “Penman”
“The pen for our army.”
Washington’s “Penman”
Hamilton’s primary task as aide: the tedious job of reading and writing letters for Washington.
“The pen for our army was held by Hamilton.” ~ Robert Troup
Numerous letters dealt with spies.
“A certain Mr. Smith”
April 1777, Gen. Lincoln caught a suspected spy.
Hamilton drafted letter for Washington to Lincoln:
The captured “Mr. Smith” was one of their spies.
Release him but make it appear as if he escaped.
“Make him a handsome present in money to secure his fidelity.”
Jacob Bankson
March 1778, Washington suspected that Jacob Bankson was a double agent.
Hamilton and Harrison drafted a letter asking Gov. Livingston to have Bankson watched.
A week later, Hamilton himself instructed Col. Moylan to ask Livingston for information and to “ascertain whether Bankson” was a spy.
In April and May, Washington paid Bankson $200. Washington wrote to Livingston that the matter was “satisfied” and he “need not trouble” himself further.
Elias Dayton’s Spies
February 1778, Hamilton drafted letter for Washington regarding “the two Hendricks and Meeker,” spies operating under Col. Elias Dayton.
July 1778, Hamilton drafted letter for Washington to Lt. Col. Barber thanking him for “intelligence” and asking how to compensate “Hendricks.”
October 1780, Hamilton himself wrote to Joshua Mersereau, another spy for Dayton, requesting intelligence regarding a rumored British attack “by way of Staten Island.”
Elijah Hunter
March 1779, Hamilton drafted letter for Washington to Gen. McDougall to be “circumspect” with “Mr. Hunter,” a double spy, and to provide him with “as little of our true circumstances as possible.”
Hamilton had written “Mr. Hunter” but Washington crossed out the letters after “H” in Hamilton’s draft and Hamilton wrote “Mr. H—-” in final letter.
Elijah Hunter turned out to be a valuable spy for Washington.
George Higday
George Higday acted as a spy “not far from the Bowery on the Island of New York.”
July 1779, Benjamin Tallmadge’s papers were captured by British.
Hamilton drafted letter for Washington to Tallmadge:
“Take care to guard against the like in future.”
Give “Higday…the speediest notice of what has happened.”
Higday was discovered, arrested, and languished in prison for more than a year.
Lessons
Just one month after joining Washington’s family, Hamilton was already involved in the “secret service.”
Hamilton knew identities of the above spies.
Hamilton corresponded directly with spies and with others about spies under their supervision.
Hamilton drafted letters to senior officers and civilian authorities instructing them how to handle certain spies.
Expert Testimonials
“Hamilton has the entire confidence of his General.”
Lafayette, 1780
Hamilton was the “principal and most confidential aid[e] of the Commander in chief.”
George Washington, 1798
Hamilton was Washington’s right-hand man: in battle, politics, government, and espionage.
Prisoners and Deserters

Extracting Intelligence
Interrogations
Three records of interrogations found in Hamilton’s hand:
Hessian deserter, October 31, 1778
Two British deserters from Halifax, November 25, 1778
James Dickson, deserter from British guards, June 15, 1780
Gained intelligence on enemy positions and troop strength.
Hamilton recorded interrogations.
Did Hamilton conduct interrogations?
Alexander Hamilton’s
Spies
Friends in
New York and New Jersey
Hamilton’s Spies
Having lived in Elizabethtown and New York City, Hamilton had more contacts in New Jersey and New York than Washington’s other aides.
Most of the war fought (or maneuvered) in New York and New Jersey.
Hamilton’s contacts sent intelligence to headquarters.
Saving the
American Army
Elisha Boudinot’s Intel and
Gen. Sullivan in Rhode Island
Elisha Boudinot
August 1778, Elisha Boudinot informed Hamilton that “General [Henry] Clinton with his whole Army has set off for Rhode Island.”
Hamilton shared intelligence with Washington.
Hamilton drafted and wrote letter for Washington warning Gen. Sullivan in Rhode Island.
Sullivan and his army retreated “in consideration of the Intelligence conveyed” by Washington and Hamilton.
Henry Clinton landed at Newport just 36 hours after Sullivan departed.
Hercules Mulligan
“Most important intelligence.”
Hercules Mulligan
Son of Liberty.
Fought in Battle of Golden Hill, January 1770.
Met Hamilton “shortly” after he arrived.
Hamilton “boarded” with Mulligan.
Mulligan and Hamilton took cannon from Battery, August 1775.
Merchant and tailor on Water Street and then Queen Street (now Pearl Street).
Hercules Mulligan, Spy
Hercules Mulligan visited Hamilton in New Jersey in November 1776. (Mulligan’s Narrative)
“After Hamilton entered the family of Washington [March 1, 1777], Mulligan became the confidential correspondent of the commander-in-chief.” (John C. Hamilton)
Hamilton apparently recruited Mulligan and handled his intelligence.
Collecting Intelligence
British and Hessian officers visited Mulligan’s store.
Officers of an infantry regiment quartered in Mulligan’s home at 23 Queen Street.
Hugh Mulligan sold goods to British.
Mulligans told or overheard news.
Hercules Mulligan relayed intelligence to headquarters.
Mulligan: Successful Spy
Details of Mulligan’s operations are uncertain.
Family traditions.
Supposedly worked with Culper Ring.
Supposedly warned headquarters in April 1777 that British would attack Philadelphia.
Supposedly warned headquarters in July 1780 that British would attack Rhode Island.
Supposedly warned headquarters of a plot to seize Washington.
Mulligan: Successful Spy
Supposedly, Arnold had Mulligan imprisoned on suspicion of being a spy and tried to have him hanged. Released after a “considerable time.”
Supposedly, Washington honored Mulligan by taking his first breakfast with him after the British evacuated New York City.
In 1789, Washington paid Mulligan at least £228 for clothing and tailoring for himself, Mrs. Washington, and his household.
Celebrating Mulligan
John C. Hamilton (knew Mulligan and son): Mulligan “furnished most important intelligence.”
GWP Custis: Mulligan “conveyed to the American commander the most important information.”
William J. Casey wanted to have statue of Nathan Hale at CIA headquarters “replaced by a statue of Hercules Mulligan” because “Nathan Hale got caught trying to get into British occupied New York” whereas Mulligan “functioned throughout the war, was never caught, never broke his cover, and rests today, still well covered, in the churchyard of Trinity Church.”
Hamilton’s Role
Mulligan himself wrote that he visited Hamilton in November 1776.
John C. Hamilton wrote that Mulligan started spying after Hamilton appointed aide on March 1, 1777.
Hamilton apparently recruited Mulligan.
As Washington’s aide and Mulligan’s friend, Hamilton likely handled Mulligan and his intelligence.
James Rivington
“Intelligence of great importance.”
James Rivington
NYC publisher of newspapers and pamphlets.
Hamilton’s A Full Vindication and The Farmer Refuted.
Leaned to the Tory side.
Hamilton reportedly tried to stop the mob that attacked his press in November 1775.
Hamilton expressed disapproval of the mob action in a letter to John Jay.
Collecting Intelligence
During the British occupation of New York City, Rivington printed The Royal Gazette.
“The Royal Gazette literally piled abuse of every sort upon the American General and the cause of America.” (GWP Custis)
As “the King’s printer,” no one suspected Rivington. (GWP Custis)
Befriended by British officers, incl. Henry Clinton.
James Rivington, Spy
Rivington was pro-British when war started.
Between 1779 and 1781, Rivington started spying for Washington.
In autumn of 1781, Rivington helped obtain the British Navy’s signal codes, which were relayed to Washington and French admiral.
James Rivington, Spy
GWP Custis: Rivington provided Washington with “intelligence of great importance, gleaned in convivial moments at Sir William [Howe]’s or Sir Henry [Clinton]’s table.” The information would then “be in the American camp before the convivialists had slept off the effects of their wine.”
Rivington: Successful Spy
Washington reportedly visited Rivington after the British occupation of New York and gave him “two heavy purses of gold” in full view of others.
GWP Custis: “The story of the secret service was related to us by the late General Henry Lee, who had it from one of the officers that accompanied the Chief.”
Numerous contemporary sources confirm that Rivington had spied for Washington. (AHTFY 392)
Hamilton’s Role
Did Hamilton or Mulligan recruit Rivington?
Washington must have asked Hamilton if Rivington could be trusted.
Hamilton and Washington decided that Rivington’s self-interest outweighed his Loyalism.
Hamilton likely handled Rivington’s intelligence (up to April 1781).
Saving the
French Fleet
Alexander Hamilton,
Elias Dayton,
and the Culper Ring
Elias Dayton’s Intelligence
Dayton to Washington, July 21, 1780:
“I have this morning received the following important intelligence… The fleets under Admirals Arbuthnot and Graves had sailed on Wednesday morning… Fifty sail of transports had gone up the sound, expecting to take troops on board at Whitestone, from whence ’tis said they are immediately to proceed to Rhode Island.”
Acting on Dayton’s Intel
Washington was “absent” when the letter arrived and not expected to “return before evening.”
Hamilton received the letter, read it, and forwarded the intelligence to Lafayette in Connecticut.
Washington returned later that day; replied to Dayton confirming receipt of letter.
Hamilton drafted letter for Washington to Rochambeau in Rhode Island, similar to one sent to Lafayette.
Counteracting the British
Washington prepared to attack New York City.
If British sail to Rhode Island, New York vulnerable.
Might induce British to cancel attack on Rhode Island.
Hamilton to Eliza: “We are . . . on our way to New York. I hope we shall take it.”
British returned without attacking Rhode Island, Washington canceled attack on New York.
French fleet saved!
The Culper Ring?
Often said that the Culper Ring was the source of the intelligence Hamilton received on July 21……
The Culper Ring?
July 20: Robert Townsend (Samuel Culper Jr.) sent intelligence about British fleet’s departure from New York City to Abraham Woodhull (Samuel Culper Sr.) on Long Island.
July 20: Woodhull wrote to Benjamin Tallmadge outlining British plans. He enclosed Townsend’s letter and gave both to Caleb Brewster to deliver to Tallmadge as quickly as possible.
July 20: Brewster took these letters across Long Island Sound to Benjamin Tallmadge.
The Culper Ring?
July 20–22: Brewster can’t find Tallmadge.
July 22 at 9 p.m.: Tallmadge received these letters.
July 22: Tallmadge forwarded letters to Washington.
July 22: Tallmadge also forwarded the intelligence to Gen. Heath in Rhode Island.
The Culper Ring?
July 23: Washington received letters from Tallmadge.
July 24: Washington thanked Tallmadge for “your favor of the 22d with letters from the Culpers enclosed,” noting that he received them “yesterday” on July 23.
Culper Ring could not have source for intelligence received at headquarters on July 21.
The Culper Ring?
Various explanations given to rescue Culper:
Tallmadge misdated letter.
Washington’s dating.
Brewster forwarded letter to Washington himself.
No evidence.
Possible if not for…
Dayton v. Culper
Woodhull/Culper: “Admiral Graves with Six Ships of the Line and . . . three more out of N Y, also 1 of 50 & 2 of 40 guns, . . . has sailed for Rhode Island.”
Dayton: “Fifty sail of transports had gone up the sound.”
Hamilton: “Fifty transports are said to have gone up the Sound.”
During and after the war, Washington repeatedly complained about Culper’s intelligence being “so long getting to hand.” (AHTFY 399–400)
Counterintelligence

“The Enemy are completely deceived”
Leaking Intelligence
May 1780: Charleston, SC, under siege. Washington received news French fleet on its way.
May 16, Hamilton drafted letter to SC Gov. Rutledge:
If Charleston about to fall, leak the news to British, which may induce them to “relinquish the siege.”
If not, keep secret so Americans can attack divided British army.
Charleston had already fallen on May 12.
Deceiving Enemy Spies
According to John C. Hamilton:
August 1781, Washington invited British spy to HQ.
Washington left a map of planned attack on New York City for spy to see.
This spy sought interview with Hamilton to confirm.
“Confident that a disclosure…of the actual intentions… would be the most certain means of deceiving him,” Hamilton at once replied, “we are going to Virginia.”
“The spy” was “thus completely duped” and informed Henry Clinton that New York City was the intended target.
Supporting Evidence
Hamilton knew Virginia was real target before British and other American officers knew (AHTFY 406–407)
Washington acknowledged using “fictitious communications” to “misguide and bewilder Sir Henry Clinton.”
Elias Boudinot gave first-hand account of a spy duped by Washington remarkably similar to above.
Perhaps the same man.
If not, another example of Washington “fictitious communications.”
Result
British thought Americans would attack New York City.
Americans marched right past New York City.
Clinton too slow to react.
Cornwallis learned too late of move against him.
Siege of Yorktown.
Cornwallis surrenders.
Americans win war.
Counterintelligence!
Hamilton’s Contributions

The Clandestine Nature of Espionage
Hamilton’s Contributions
Helped Washington with his “secret service.”
Letters to spies.
Letters to spy ringleaders.
Instructions to generals and governors regarding intelligence.
Interrogations.
Recruited and managed spies.
Received and acted upon incoming intelligence.
Deceived enemy spies.
The Clandestine
Nature of Espionage
Much is uncertain.
Many letters have been lost or were destroyed.
Even more was probably never recorded.
Hamilton surely did more than is known.
Must be careful about claims without evidence.
New discoveries are waiting to be found!
Alexander Hamilton
Spymaster
Michael E. Newton
Alexander Hamilton: The Formative Years