25 Most Prolific Spies And Their Top Secret Missions

Although their exploits are often popularized by Hollywood and quite often ride the line between completely unbelievable and just barely possible, spies really do exist. Of course, they are probably not running along the outsides of high rise buildings and paragliding into jungles but they do work as undercover diplomats, engineers, and lay people. They risk their lives in both war and peace, sometimes for a noble cause and sometimes for nothing more than the highest bidder. Enter the shady underworld of espionage as you learn about history’s 25 most prolific spies and their top secret missions.

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25

Nathan Hale

Nathan Hale

Famously known as the “first American spy,” Hale was a soldier for the continental Army during the American Revolutionary War in 1775. He was officially designated the state hero of Connecticut after he volunteered to go behind enemy lines and observe the movements of the British during the Battle of Long Island. Disguised as a Dutch teacher on his way to New York, he was eventually caught by the British and hanged.

24

Major John Andre

Major John Andre

A British Army officer who was hanged in 1780 as a spy during the American War of independence, Andre was a favorite in colonial society during the British occupation in both Philadelphia and New York. He became adjutant-general with the rank of Major in 1778 and in the following year had contrived with American General Benedict Arnold, commander of West Point, to surrender it to the British for £20,000 so that New England would be cut off from the rest of the rebel colonies. He was found guilty of being behind enemy lines when he was caught traveling to New York using civilian clothes and a fake passport supplied by Arnold. Although he was well-liked by both sides he was hanged on October 2, 1780.


23

James Armistead Lafayette

James Armistead Lafayette

A slave owned by William Armistead of Virginia, he became the first African-American double agent during the American Revolution. He volunteered in 1781 to join the army under General Lafayette after getting the consent of his master. His first mission was to spy on Brig. Gen. Benedict Arnold, who had defected from the Continental Army to lead the British forces. His espionage reports were considered instrumental in defeating the British forces during the Battle of Yorktown.

22

Belle Boyd

Belle Boyd

Maria Isabella Boyd or the ‘”Cleopatra of the Secession,” was a Confederate spy during the American Civil War operating from her father’s hotel, the Front Royal. She conveyed valuable information to General Stonewall Jackson in 1862 through her slave Eliza Hopewell as she charmed military secrets out of one of her Union sentries. She was awarded the Southern Cross of Honor due to her contributions.


21

Emeline Pigott

Emeline Pigott

A spy for the Confederate Army in North Carolina, Pigott organized fishermen to spy for her as she hid secret messages in her skirt and carried them from New Bern through the sea ports to be transmitted to the proper authorities. Though she had been arrested by the Union forces several times on charges of blockade running, she still continued on. She oftentimes entertained Yankee soldiers at her parent’s farm so as to distract them while her brother-in-law, Rufus Bell, carried food to the Confederates hiding in the nearby woods.



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