Nathan Hale
One of America’s very first spies – and, certainly, according to the CIA, the first to be executed for espionage – Nathan Hale was, to many, a true hero of the independence struggle. He was young, fearless and brave and is remembered with great admiration. Indeed, there’s even a statue of him, along with his famous last words (“I only regret that I have but one life to lose for my country”) at the CIA headquarters. But was he actually any good at spying? Sadly, it would appear not. In fact, according to some historians, he was completely out of his depth when he undertook his first – and last – mission as a secret agent.
That’s not to say he wasn’t enthusiastic about the role. Or even to doubt his bravery. Undoubtedly, he was both. At the age of just 21 and fresh out of Yale, he answered General George Washington’s call for volunteers to venture behind enemy lines and report on British army size and movements. Notably, Hale was the only man to step forward, a testament to his bravery. However, despite having been made a captain in the Continental Army, he knew nothing about the art of spying. Tragically, he didn’t receive any training in espionage or subterfuge either. Instead, in September of 1776, he was just given a set of civilian clothes and sent on his way across enemy lines.
It wasn’t long before Hale caught the attention of Major Robert Rogers. While Rogers, a Brit who had served with distinction in several previous conflicts, was a skilled and experienced outdoorsman, Hale was nothing of the sort. In fact, he looked so out of place in the open that Rogers immediately suspected he was up to something and decided to follow him. After a couple of days, he made his approach. The pair struck up an easy conversation, and soon the talk shifted to the war. Surely Hale, as a spy deep in enemy territory, would keep his mouth shut. Apparently not.
Despite having just met Rogers, the younger man willingly revealed himself to be a spy and told him of his mission. He even repeated his claims over dinner at Roger’s house. As one historian, writing for the Library of Congress’s Information Bulletin, noted: “How could anyone on a secret mission be so stupid, or to use more generous terms, so naïve or credulous, to be taken in by a perfect stranger and then to disclose, the next day, the object of his mission to several more perfect strangers.”
Tragically, such naivety was to be harshly punished. Hale was brought before the British authorities and convicted of spying. He was hung the next morning, right after saying his famous last words. History has been more forgiving, and Hale has long been considered a true American icon and is even the designated state hero of Connecticut.