During the eight long years of the Revolutionary War, both British and American commanders employed creative and dangerous tactics in an attempt to gather valuable military intelligence that could give their armies an edge on the battlefield. One common but incredibly risky method of obtaining such intelligence was to have a soldier pretend to “defect” to the opposing side. There, the phony defector would earn the enemy’s trust by offering attractive (and often false) information, then linger in the area long enough to gather whatever intelligence they could before sneaking back into friendly territory.

This was the tactic employed by Sergeant Daniel Bissell in 1781, a Connecticut native who answered George Washington’s request to gather intelligence on the ongoing British occupation of New York City. Bissell, born in what is now East Windsor in 1757, was a man whose loyalty to the American cause appeared beyond reproach; he had been serving in the Continental Army since 1777. His impeccable service record made the discovery of his “defection” on the night of August 13, 1781 all the more shocking to his comrades in the 2nd Connecticut Regiment — and all the more attractive to the British soldiers who welcomed Bissell across their lines the following day.

Soon after he entered New York City, Bissell took the extraordinary step of enlisting in a British regiment — a move that added even more risk to his mission, since he could technically be tried as a traitor by the Americans were he ever to take up arms against the Continental Army in battle. Bissell insisted that he only did so to avoid being “pressed” into service aboard a British naval vessel. Regardless of the reason, records confirm Bissell’s claim that he was hospitalized with a feverish illness for most of the thirteen months he spent behind enemy lines, rendering him unable to participate in any military action against his countrymen. Bissell was, however, able to gather detailed intelligence on British fortifications and military strength while in New York City, and was able to draw intricate maps of British forts from memory as soon as he slipped back to the American lines in September of 1782.

In acknowledgment of his efforts, undertaken at great risk to himself, Bissell became the third and final known recipient of the Badge of Military Merit, the Revolutionary War-era emblem that later inspired the U.S. military’s Purple Heart medal. George Washington praised Bissell in his General Orders of June 8, 1783 for “having per­formed some important services, within the immediate knowledge of the Commander in chief, in which the fidelity, perseverance, and good sense of the said [Sergeant] Bissell were conspicuously manifested.”

Further Reading

Todd W. Braisted, “A Spy Wins a Purple Heart: The Amazing Tale of Daniel Bissell and the Military Order of Merit,” Journal of the American Revolution

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