August 13: A Patriot Defects to the Redcoats



During the eight long years of the Revolutionary War, both British and American commanders employed creative and dangerous tactics in the attempt to gather military intelligence that could give their armies a battlefield advantage. One common but highly risky method of obtaining such intelligence was to have a soldier pretend to “defect” to the opposing side. Once there, the phony defector would earn the enemy’s trust by offering attractive (and often false) information, then linger long enough to gather useful intelligence before returning to friendly territory.

This was the tactic employed by Sergeant Daniel Bissell, a Connecticut native who answered George Washington’s 1781 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, as he had been serving in the Continental Army continuously since 1777. His impeccable service record made the discovery of his “defection” on the night of August 13, 1781 a shock to his comrades in the 2nd Connecticut Regiment. It also made Bissell all the more attractive to the British soldiers who welcomed him across their lines the following day.

Some of the intelligence related by Daniel Bissell upon his return to the American lines in September 1782, including a sketch of a British fort on Staten Island. (George Washington Papers, Library of Congress)

Shortly after he entered New York City, Bissell took the extraordinary step of enlisting in a British regiment. This added more risk to his mission, since he could technically be tried as a traitor by the Americans were he ever to actually fight against the Continental Army in battle. Bissell insisted that he only joined the British army to avoid being “pressed” into service aboard a British naval vessel. Regardless of the reason, records confirm Bissell’s later claim that he was hospitalized with a feverish illness for most of the thirteen months he spent behind enemy lines, which rendered him unable to participate in any military action against his countrymen. He was, however, able to gather detailed intelligence on British fortifications and military strength while in New York City, and 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 created by George Washington that later inspired the U.S. military’s Purple Heart medal. 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