Caleb Brewster

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Caleb Brewster
Allegiance  United States
Service Continental Army

Born (1747-09-12)September 12, 1747
Setauket, New York[1]
Died February 13, 1827(1827-02-13) (aged 79)
Black Rock, Connecticut[1]

Caleb Brewster (September 12, 1747 – February 13, 1827) was a member of the Culper spy ring during the American Revolutionary War, reporting to General George Washington through Major Benjamin Tallmadge. Brewster not only carried messages to and from the Ring's main spies in Setauket, New York and New York City across Long Island Sound from and to Tallmadge, but made some direct reports to Washington concerning naval activities in the New York City area. Abraham Woodhull and Robert Townsend, alias "Samuel Culper, Sr." and "Samuel Culper, Jr." respectively, were the main agents in the Ring. Tallmadge was referred to by the alias "John Bolton."[2] As a Continental Army officer serving under Tallmadge, Brewster also participated in military actions.

Brewster was born in Setauket, New York,[1] a hamlet now part of the town of Brookhaven. He was the son of Benjamin Brewster, grandson of Daniel Brewster, and great-grandson of the Rev. Nathaniel Brewster (the first minister of the old town church in Setauket).[3]

After the Revolutionary War, Brewster was a blacksmith, an officer in the United States Revenue Cutter Service for 20 years and a farmer.

Culper Ring[edit]

On August 25, 1778, Major Benjamin Tallmadge convinced General George Washington that Abraham Woodhull of Setauket, Long Island, New York would make a good agent to gather intelligence in New York City, the British Army's headquarters and base of operations during the American Revolutionary War.[2] By October, Washington gave Tallmadge the assignment to set up a network of spies and couriers in New York City.[4] In October 1778, Tallmadge started the New York City operation with Woodhull making trips into New York, ostensibly to visit his sister, Mary Underhill, who operated a boarding house with her husband Amos Underhill.[5] Woodhull sent his messages under the alias "Samuel Culper," later as "Samuel Culper, Sr."[2]

At first, Woodhull had to return to Setauket to pass messages to Brewster to take to Tallmadge or to receive messages from Tallmdadge via Brewster.[6] By December 1778, Tallmadge set up couriers, at first Jonas Hawkins, then mainly Austin Roe, who would take messages the 55 miles (89 km) between New York and Setauket to pass them to Brewster.[7] According to widely accepted local and family tradition, Anna Strong's role in the Ring was to signal Brewster, who ran regular trips with whaleboats across the Sound on a variety of smuggling and military missions, that a message was ready. She did this by hanging a black petticoat on her clothesline at Strong Point in Setauket, which was easily visible by Brewster from a boat in the Sound and by Woodhull from his nearby farm after he began to operate mostly from home in Setauket.[8][9][10] She would add a number of handkerchiefs for one of six coves where Brewster would bring his boat and Woodhull would meet him.[11][12][13] Historian Richard Welch writes that the tradition of the clothesline signal is unverifiable but it is known that the British had a woman at Setauket who fits Anna's profile under suspicion for disloyal activities.[14]

In February 1778, Brewster sent one of the messages of his own which concerned naval matters, the building of flat bottom boats in New York which could be used to ferry troops and the outfitting of Loyalist privateers through the Culper channel.[15]

Woodhull became increasingly anxious about being away from Setauket for long periods of time, and by British counter-espionage actions.[6] So in June 1779, Woodhull engaged Robert Townsend, who used the alias "Samuel Culper, Jr." to gather intelligence in New York City.[16] Since Townsend was engaged in business there, his presence was expected to arouse less suspicion than Woodhull's would. He also had access to British officers through the authorship of a society column in a Loyalist newspaper and his tailoring business, as well as his interest in a coffeehouse with Loyalist newspaper owner James Rivington, who also was a secret member of the Ring.[9][17]

A network was then established in which Townsend would pass intelligence to a courier, almost always Hawkins, until September 1779, or Roe, who would take it 55 miles (89 km) to Setauket and pass it to Woodhull, usually via dead drop.[18] Woodhull would evaluate and comment on it and pass it to Caleb Brewster, who would take it across Long Island Sound, occasionally adding an intelligence note of his own, and pass it to Tallmadge, who would usually add a cover letter with comments. Tallmadge found that personally taking the message to Washington was too time consuming. So he sent messages after the first one to Washington by a dragoon, then by a relay of dragoons, acting as couriers.[18][7]

On one of his trips to Setauket, Brewster was waiting for Woodhull in Anna Strong's back garden.[19][20] While waiting, he surprised a passing British lieutenant, pulled him off his horse and had the opportunity to capture or kill him.[20] He refrained from doing so in order to avoid drawing suspicion on Anna as a member of the Ring, by leaving the impression that Brewster and his men were thieves.[19][20]

On February 4, 1781, the double agent, or simply self-dealing mercenary, William Heron told British intelligence chief Major Oliver De Lancey of the Seventeenth Light Dragoons that private dispatches were being sent from New York City by some traitors to Setauket "where a certain Brewster received them near a certain woman's."[21] Since the British were never able to catch Brewster and get him to disclose the woman's name, Anna Strong's identity as a member of the Ring remained secret.[21]


Brewster married Anne Lewis of Fairfield, Connecticut after the war and moved to Fairfield with her.[22] He set up a blacksmith business.[23] In 1793, Brewster joined the United States Revenue Cutter Service, predecessor of the United States Coast Guard.[23] He took three years off from the service because he disagreed with policies of President John Adams. From 1812 to 1816, Brewster commanded the revenue cutter, USRC Active (1812).[23] He retired to his farm in Black Rock, Connecticut.[23] Caleb and Anne Brewster had eight surviving children.[23] Brewster died February 13, 1827, aged 79, and is buried in Fairfield Cemetery.[23]

In popular culture[edit]

Caleb Brewster is played by Daniel Henshall in the TV series Turn: Washington's Spies, on AMC.

External links[edit]

See also[edit]


  1. ^ a b c Caleb Brewster Papers, 1755-1976.
  2. ^ a b c Rose (2007), p. 75.
  3. ^ Mather (1913), pp. 278–279.
  4. ^ Rose (2007), p. 7p.
  5. ^ Rose (2007), pp. 88, 90.
  6. ^ a b Rose (2007), p. 101.
  7. ^ a b Rose (2007), p. 102.
  8. ^ Baker (2014), p. 124.
  9. ^ a b Nelson (2011b), p. 763.
  10. ^ Naylor (2012), p. 38, [1].
  11. ^ Hunter, 2013, p. 42.[full citation needed]
  12. ^ Owen (2002), p. 21.
  13. ^ Brady (2013), p. 172.
  14. ^ Welch (2014), p. 37.
  15. ^ Rose (2007), p. 103.
  16. ^ Rose (2007), p. 132.
  17. ^ Rose (2007), pp. 150-154.
  18. ^ a b Nelson (2011a), p. 217.
  19. ^ a b Phelps (2013), p. 529.
  20. ^ a b c Rose (2007), p. 234.
  21. ^ a b Rose (2007), p. 247.
  22. ^ Rose (2007), p. 273.
  23. ^ a b c d e f Rose (2007), p. 278.