Caleb Brewster

Brewster was born in Setauket, New York,[2] a hamlet of Brookhaven, and was a descendant of Mayflower passenger William Brewster.[3] After the Revolutionary War, he was a blacksmith, an officer in the United States Revenue Cutter Service for 20 years, and a farmer.

Major Benjamin Tallmadge convinced General George Washington on August 25, 1778, that Abraham Woodhull of Setauket, Long Island, 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.[4] Brewster served as a courier in what became the Culper spy ring, carrying messages between Woodhull and Tallmadge,[5] and he ran regular trips in whaleboats across the Sound on a variety of smuggling and military missions. Woodhull and Robert Townsend were the main agents in the Ring, alias "Samuel Culper, Sr." and "Samuel Culper, Jr." respectively.[4] Brewster also participated in military actions as a Continental Army officer serving under Tallmadge.

Anna Strong's role in the Ring was to signal Brewster that a message was ready, according to widely accepted local and family tradition. She did this by hanging a black petticoat on her clothesline at Strong Point in Setauket, which Brewster could see from a boat in the Sound and Woodhull could see from his nearby farm.[6][7][8] She would add a number of handkerchiefs for one of six coves where Brewster would bring his boat and Woodhull would meet him.[9][10][11]

In February 1778, Brewster sent a message of his own through the Culper channel which concerned flat-bottomed boats being built in New York which could be used to ferry troops, and Loyalist privateers being outfitted.[12] On another trip, he was waiting for Woodhull in Anna Strong's back garden[13][14] when he surprised a passing British lieutenant. Brewster pulled him off his horse and had the opportunity to capture or kill him,[14] but he refrained from doing either in order to avoid drawing suspicion on Anna as a member of the Ring, and instead pretended that he and his men were thieves.[13][14]

Brewster married Anne Lewis of Fairfield, Connecticut, after the war and moved to Fairfield with her,[15] where he set up a blacksmith business.[16] The couple had eight surviving children.[16]

In 1793, he joined the United States Revenue Cutter Service, predecessor of the United States Coast Guard.[16] He took three years off from the service because he disagreed with policies of President John Adams, and he commanded the revenue cutter USRC Active (1812) from 1812 to 1816.[16] He retired to his farm in Black Rock, Connecticut.[16]

Brewster died February 13, 1827, aged 79, and is buried in Fairfield Cemetery.[16]

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

• Intelligence in the American Revolutionary War
• Intelligence operations in the American Revolutionary War

• Baker, Mark Allen (2014). Spies of Revolutionary Connecticut: From Benedict Arnold to Nathan Hale. Charleston, South Carolina: The History Press. ISBN 978-1-62619-407-6.CS1 maint: ref=harv (link)
• Brady, Kevin M. (2013). Frank, Lisa Tendrich (ed.). Culper Spy Ring. An Encyclopedia of American Women at War: From the Home Front to the Battlefields. Santa Barbara, California: ABC-CLIO. ISBN 978-1-59884-444-3.CS1 maint: ref=harv (link)
• Brewster, Caleb. "Caleb Brewster Papers, 1755-1976". Fairfield Museum and History Center. MS 33. Retrieved March 17, 2013.
• Mather, Frederic Gregory (1913). The Refugees of 1776 from Long Island to Connecticut. Albany, New York: J. B. Lyon. p. 278. ISBN 978-1-55613-342-8.CS1 maint: ref=harv (link)
• Naylor, Natalie A. (2012). Women in Long Island's Past: A History of Eminent Ladies and Everyday Lives. Charleston, South Carolina: The History Press. ISBN 978-1-60949-499-5.CS1 maint: ref=harv (link)
• Nelson, David Paul (2011a). Hastedt, Glenn, P. (ed.). Culper Ring. Spies, Wiretaps, and Secret Operations: A-J. Santa Barbara, California: ABC-CLIO. ISBN 978-1-85109-807-1.CS1 maint: ref=harv (link)
• Nelson, David Paul (2011b). Hastedt, Glenn, P. (ed.). Robert Townsend. Spies, Wiretaps, and Secret Operations: A-J. Santa Barbara, California: ABC-CLIO. ISBN 978-1-85109-807-1.CS1 maint: ref=harv (link)
• Owen, David (2002). Hidden Secrets. Toronto: Firefly Books. ISBN 978-1-55297-564-0.CS1 maint: ref=harv (link)
• Phelps, Mark Anthony (2013). Frank, Lisa Tendrich (ed.). 355. An Encyclopedia of American Women at War: From the Home Front to the Battlefields. Santa Barbara, California: ABC-CLIO. ISBN 978-1-59884-444-3.CS1 maint: ref=harv (link)
• Rose, Alexander (2007) [2006]. Washington's Spies: The Story of America's First Spy Ring. New York: Bantam Dell. ISBN 978-0-553-38329-4.CS1 maint: ref=harv (link)
• Welch, Richard F. (2014). General Washington's Commando: Benjamin Tallmadge in the Revolutionary War. Jefferson, North Carolina: McFarland. ISBN 978-0-7864-7963-4.CS1 maint: ref=harv (link)

• The Caleb Brewster letter correspondence including with George Washington