The American general was desperate. The last time he had faced his enemy counterpart, who considered one the best tacticians in the world, he and his men had barely escaped with their lives and had given up crucial territory during the withdrawal. He knew that he could be engaging in a second battle at any time and that if he were to be victorious, he needed crucial information on the enemy’s position and plans.

He knew that in order to get this intelligence, he would need to get someone into enemy territory. He needed a spy. He put out the call, and one man immediately volunteered. The general was George Washington, his enemy was General William Howe, and the battle would take place on September 16, 1776, at Harlem Heights, Manhattan. The spy who stepped forward was Nathan Hale.

Almost everyone knows the fate of Hale. Receiving his orders from Washington, he set out on his mission and successfully penetrated British lines, posing as a Dutch schoolmaster. For a week, Hale carried out his mission, gathering information on enemy positions before attempting to make his way back to American lines. He was almost home free when he was set upon by a British patrol, which discovered the documents that he had drawn and notes that he had taken.

According to an article in the Library of Congress’s online publication, “America’s Library,” it is believed that Hale was betrayed by a cousin who sympathized with the British and was, at the time, under Howe’s command. Whatever the reason, Hale is said to have uttered the famous epitaph, “I only regret that I have one life to give for my country,” before he was hanged on September 22, 1776. He was 21 years old.

Although by far the most famous of the Revolutionaries ragtag and unorganized intelligence operators, Hale was far from the only one. Though not an intelligence operator in the traditional sense, Paul Revere, after learning of British General Thomas Gage’s plans for a surprise midnight raid to seize the weapons of rebel colonists in Lexington, Massachusetts, determined to warn patriot leaders John Hancock and Samuel Adams of the impending attack. He borrowed a horse and rode off into the night of April 18, 1775.

Even his wife, Rachel, got in on the game. Overhearing that the British were on to her husband, she attempted to contact him via a wax-sealed letter containing a warning and 125 British pounds. The problem for Rachel was that the British had their own intelligence network that was quite extensive and well organized, and unfortunately, Rachel passed the letter to one of its operators — Dr. Benjamin Church.

Church promptly turned the letter over to British authorities. Revere was able to deliver his warning to the rebel leaders, but his “The British are coming!” midnight hollering was cut short when he was stopped by a British patrol. Fortunately, in their haste to join the impending fight at Lexington, they let him go.

Probably the most infamous British spy was Benedict Arnold. Arnold began his military career as a militia captain. He soon gained a reputation as a ferocious fighter and tactician, but also as a divisive character making many enemies among his own men. According to a biography, Arnold was even brought up on charges of misappropriation of funds and faced a court-martial.