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.
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.
[5] He chose several men from eastern Long island, including half-brothers David and Benjamin Dickerson who were on active duty in another command within the Continental Army.
I beg that you will order them back to their late duty under a careful & attentive sergeant.”[6] Anna Strong's role in the Ring was to signal Brewster that a message was ready, according to widely accepted local and family tradition.
Brewster pulled him off his horse and had the opportunity to capture or kill him,[15] 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.