![]() ![]() The job required Crosby to work deep undercover. Crosby played along and later reported what he learned to Patriot leader John Jay, who seized the opportunity to recruit him as one of the nation’s first counterintelligence operatives. In 1776, the Connecticut-born shoemaker was making his way to a Continental Army camp in New York when he was confused for a British sympathizer and invited to a meeting of loyalist militiamen. Enoch Crosbyįrench map of the Hudson River Valley and surrounding area, New York, 1778.Įnoch Crosby’s spy career began with a simple case of mistaken identity. One of their most significant achievements came during the summer of 1780 when they informed Washington of a British plan to ambush French forces gathered at Newport, Rhode Island. Once smuggled out of the city, the documents would be ferried to Tallmadge’s coastal Connecticut headquarters by a fleet of whaleboats operated by an agent named Caleb Brewster.ĭespite operating from the heart of enemy territory, Tallmadge’s Culper Ring managed to gather intelligence for some five years without losing a single agent to the British. He even had them write some of their reports in invisible ink that could only be read after being brushed with a chemical compound. Tallmadge instructed his operatives to communicate via a complex system of dead drops and coded messages. Operating under the pseudonym John Bolton, he recruited childhood friend Abraham Woodhull and several other acquaintances to provide intelligence from in and around British-controlled Long Island. The New York native first organized the cabal in late 1778 at the behest of General George Washington. Serving with distinction at the Battles of White Plains, Brandywine, and Germantown, Continental dragoon Benjamin Tallmadge was also the mastermind behind the Culper Spy Ring, one of the most effective espionage networks of the American Revolution. As a sign of his gratitude to his former commander, Armistead later changed his name to James Armistead Lafayette.ģ. He finally won his release papers in 1787, thanks in part to Lafayette, who wrote a letter to the Virginia legislature on his behalf. ![]() In July 1781, he was one of the first sources to inform Lafayette that the British were marshaling their forces at Yorktown.ĭespite having risked his life for his country’s freedom, Armistead was sent back to his master after the war and held as a slave for several more years. He also kept his ears open for any word of enemy movements. Armistead agreed and immediately began funneling the Redcoats' phony information supplied by Lafayette, including a fraudulent report that referenced nonexistent units of Continental troops. He proved so convincing in the undercover role, that Cornwallis eventually enlisted him to work as a British spy. He then graduated to full-blown espionage in the summer of 1781, when he infiltrated Charles Cornwallis’s camp by posing as a runaway slave loyal to the British. The Virginia-born bondsman began his service by transporting dispatches and intelligence reports across enemy lines. James Armistead Lafayette (R) at Yorktown, standing with Marquis de La Fayette (L).ĭuring the Yorktown campaign, the Marquis de Lafayette found an unlikely secret agent in James Armistead, a black slave who got his master’s permission to assist the Continental Army. He was ferried across the Long Island Sound on September 16, slipped into the occupied town of Huntington and began surveying British fortifications and encampments while posing as a schoolmaster. When General George Washington’s forces became bottled up on Manhattan Island in September 1776, Hale volunteered for a mission to gather much-needed intelligence behind enemy lines. Often dubbed “America’s first spy,” Nathan Hale was a Yale graduate who served in Knowlton’s Rangers, a short-lived Continental reconnaissance unit. Accounts of Hale's final words vary, but according to written reports and popular legend, the 21-year-old patriot faced the gallows “with great composure and resolution” before uttering the famous words, “I only regret that I have but one life to give for my country.” Charged as an illegal combatant, he was executed by hanging on the morning of September 22. Hale was arrested the next day and discovered to have incriminating documents concealed beneath the soles of his shoes. It only took a few days before his suspicious questions drew the attention of loyalist locals, and he later blew his cover after a British agent approached him in a tavern and pretended to be a fellow Patriot spy. Hale was undoubtedly courageous, but according to most historians, he wasn’t a very skilled intelligence officer. ![]()
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