Benedict Arnold: From Hero to Insider Threat and Traitor

On a paved landing nestled within Saratoga National Historical Park in New York stands an unassuming monument surrounded by an iron fence. The front of the granite relief is an intricately carved man's boot. Inscribed on the back are the words:

"In memory of the 'most brilliant soldier' of the Continental Army, who was desperately wounded on this spot… 7th October 1777, winning for his countrymen the decisive battle of the American Revolution and for himself the rank of Major General."

The "most brilliant soldier" is referring to Benedict Arnold, left unnamed because he's a controversial figure-one of the most notorious traitors in U.S. history. Few remember him as one of America's finest battlefield generals at the start of our war for independence. But the mighty military man and crafty intelligence practitioner was once as heroic as he was treacherous.

It is impossible to tell the story of Benedict Arnold as separate from the story of America.

Auspicious Beginnings

Born in Norwich, Connecticut in 1741, Benedict Arnold had a prosperous start to life. His father was a successful merchant. However, the Arnold family fortunes suffered due to personal challenges as well as the taxes and trade restrictions Britain imposed on the colonies as a means of control. In 1767, Arnold married his first wife, who died young, and became a shipping entrepreneur in his own right.

A Brilliant Field Commander

With the outbreak of the Revolutionary War in 1775, Arnold, then a devoted Patriot, was made captain of his colonial militia unit. By year's end, the Second Continental Congress ordered him to lead troops against the British in Quebec. The Americans lost, but Arnold showed bravery, resilience, and sound combat judgment. Arnold further showcased his military prowess in 1777, when he rallied the Continentals to victory in the Battle of Saratoga. Twice during Arnold's burgeoning military career, he overcame serious injuries inflicted by the Redcoats.

Path to Perdition

The hero's fall began in 1778 when Continental Army General George Washington, who held Arnold in high esteem, installed him as military governor of Philadelphia to restore order after British troops left to focus on New York.

Away from the battlefield, Arnold enjoyed the social scene. Too much, it seems. He was fraternizing with Loyalists and living beyond his means. It wasn't long before he re-married and ran into some legal and financial troubles.

These added to Arnold's long-simmering resentments over perceived ill-treatment by Congress, which persuaded Arnold to betray the American cause. First, he planned on sharing intelligence about Washington's movements with the British, which would enable them to capture or kill Washington. Next, Arnold planned to hand America's vital West Point fortifications to the British and, in doing so, reveal his treason and become a high-ranking British officer.

Skilled Intelligence Practitioner Goes Rogue

Arnold's smarts served him well as he schemed to sell out his country, and he used stealth and guile to get away with it. But how did he learn spy tradecraft in an era before professional intelligence organizations? In short, it was on-the-job experience. Like other high-ranking military officers of his day, Arnold was expected to run his own intelligence affairs, from tactical and strategic planning, to collecting information and analyzing it in support of his combat operations.

Let's examine the progression of Arnold's intelligence practices.

The Art of Deception

Perhaps no event reveals Arnold's mastery of deception better than his covert operation to rescue a besieged American fort without firing a shot. Shortly before rising to the occasion at Saratoga, Arnold led a small force to relieve New York's Fort Stanwix, which had been taken over by a large contingent of British, Loyalist, and Native American fighters.

Knowing he lacked the numbers to free the fort through force, Arnold orchestrated a ruse. First, he alerted enemy troops of his impending attack and, to instill fear, threatened that those who did not join his side could expect "no mercy." Next, he planted a rumor in the British camp that his force was much larger than it actually was and that it was on the move. Finally, Arnold coerced a turncoat Loyalist, who was viewed by the Native Americans as a shaman, into warning them in person, which prompted the Natives to flee on the eve of Arnold's arrival. The small force then walked unimpeded into Fort Stanwix to the cheers of their fellow Patriots.

Intermediaries and Pseudonyms

Arnold leveraged these same intelligence skills when he switched allegiances with the backing of his Loyalist wife. To conceal his offer to serve the British in June 1779, Arnold used a mutually trusted go-between to carry the letter that he signed with the pseudonym "Monk," after George Monck, a prominent military figure, who helped restore the monarchy in 1660 and was awarded the title of duke.

While working for the British, Arnold adopted several different pseudonyms and created them for his co-conspirators, most notably British Army Major John Andre, also known as "John Anderson."

Hidden and Encrypted Communication

Arnold shared military secrets on the movements of the Continental Army and its French allies, which required increasingly sophisticated methods to conceal his collaboration. He used a cipher in which a handwritten letter contained numbers that corresponded to locations of the intended word in a designated book. Arnold also obfuscated his handwriting and wrote with invisible ink, which could be revealed by heating the page or applying a reagent.

Human Intelligence

Intelligence is a business, and the British were not interested in working with Arnold unless he held a key post with access to what they needed to quash the American rebellion. So, in 1780, Arnold took advantage of General Washington's trust in him to secure command of West Point, a strategically important site.

Once in place, Arnold networked with peers to glean useful information for the British and cover his own tracks. He tried-mostly unsuccessfully-to learn the names of his predecessor's agents and planned to compromise two local double agents working for the Patriots.

The Ultimate Betrayal

One day, five years into the Revolutionary War, General Washington informed Arnold that he would be passing through West Point for a visit. Arnold saw this as his big chance. He devised a plan that would allow the British to capture Washington and assume control of the military fortress. Success could doom the new Republic and bring the colonies back into the British fold. In return, he negotiated a senior rank in the British Army and a large sum of money.

The well-planned scheme turned when Arnold's accomplice, Major Andre, became stuck behind American lines and encountered several militiamen. Andre was disguised as a merchant but mistakenly revealed his status as a British officer. The Patriots questioned him and discovered incriminating documents hidden in his belongings. Andre was executed as a spy and the West Point plot was foiled-but not before Arnold fled onto a nearby British warship, forever cementing his legacy of treachery.

Glory Beyond Benedict Arnold

Arnold's successful military ventures on behalf of the British, including capturing the new Virginia capital of Richmond, continued to vex his former compatriots until America won the decisive Battle of Yorktown in 1781, upon which he left for England to live in exile with his family. Two years later, the British Crown signed a peace agreement. America, against all odds, had won the war of independence. And the hard-fought victory was sweeter in light of the bitter betrayal.

Arnold was never fully embraced in his new homeland and passed away in London at the age of 60. His forever-tarnished legacy was the only justice for his crimes.

The life of Benedict Arnold-a single traitor at a crucial point in time-serves as a cautionary tale of the close-call that almost spelled the end of the American cause. It also reminds us why CIA and our partners in U.S. intelligence must remain ever-vigilant against insider threats to help ensure America's enduring freedom and success.