Patriot Games: The Making and Unmaking of an Old-school Intelligence Handler

Author’s note: The following is a mix of author-generated hypothesis and researched fact, written to provide historic and modern intelligence operations parallels.

I imagine that the conversation went something like this (with a lot of liberty taken here):

Clerk: “Sir, there is someone here to see you. He says that you are expecting him, and that he has important information about the American base, and will only speak with you.”

Officer: “Very good, show him in.”

The man is shown in, pleasantries are exchanged, and then it is down to business.

Officer: “Now, what can I do for you, good sir?”

In fact, he knew who the visitor was as soon as he walked into his office, as they had been corresponding on a friendly basis for some time. The visitor, also knowing these facts, decided to play the game.

Visitor: “I am here to offer you complete surrender of my military facility. It may take a bit of bloodletting on both sides, but I can ensure you that you will take control.”

Officer: “That is a very interesting offer. What led you to make this most dangerous decision?”

Visitor: “Well…let’s just say that my ‘talents’ were being over-utilized but under-appreciated, and I believe that you can help to remedy that.”

The date was May 10, 1779, and the officer, Major John Andre, Adjutant General to British Army Commander-in-Chief Sir Henry Clinton, sat back in his high-topped chair and showed the slightest hint of a smile. He stuck out his hand. “I do believe I can help you remedy that, General Arnold.”

By the time the conversation was over, American General Benedict Arnold had become what in the modern intelligence world is called a write in/walk in. Arnold offered Andre and the British the fort under his command—West Point. At the time, West Point was a major chokepoint and key to control of the Hudson Valley and New England. Its surrender would be a major injury to the Americans and a strategic advantage for the British. And now the very man that could make that happen was sitting in front of Andre and was willing to do it of his own volition.

This was not the first meeting between the two. Arnold had been introduced to Andre through his wife, Peggy Shippen, a Tory who was reportedly enthralled with Andre. Benedict Arnold admired John Andre almost as much as his wife did. The Englishman was a rising star in the British military and among the British loyalist community in the colonies. He was taken prisoner after the siege of Fort St. Johns, Newfoundland, and as was not uncommon at the time, was allowed to house with a local family because he was an officer, a lieutenant.

After he was exchanged for American prisoners near the end of 1776, Andre impressed British General Howe by presenting him with a full report based on his observations while a captive. Howe promoted Andre to captain and appointed him as aide-de-camp to Major General Charles Grey. In November 1778, Andre was promoted to major. He made his official debut in the intelligence world when he was tapped by General Henry Clinton, General Howe’s successor and British commander-in-chief, to coordinate and head British intelligence operations in the American colonies and territories.

As an intelligence officer, Andre was almost born for the part. He was educated, sophisticated, and charming. During his time as a prisoner, he endeared himself to his hosts by teaching their young son art, and in the Lancaster community where he was held, his ability to speak German, courtesy of two years of military training he underwent in Germany in 1771, made him even more popular. Add to this his almost photographic memory and need to both record and control everything, and he had the makings of a good case officer.

Benedict Arnold, in his mind, had good reason to approach the British, and he was not unique in this. Part of Andre’s job as an intelligence officer would have been to gather information on the American officers within his area of operations, then determine which ones would be most susceptible to corruption. He also knew that men (and women) spy for any number of reasons, with the most often encapsulated in the modern acronym M.I.C.E (money, ideology, compromise or coercion, and ego or extortion).

Andre, in establishing rapport with the American, would have been able to ascertain that Arnold fell into three of the four categories: Money, Ideology, and Ego. First, Arnold had demanded compensation, whether the West Point operation was a success or failure (which turned into months of back and forth negotiation, as General Clinton demanded success before payment.)

Second, Arnold’s wife was a Tory Loyalist, and Arnold had made it known to Andre that he was not only angry at the colonial rejection of a British offer of self-governance, but also at the establishment of an American/French alliance. Lastly, he was nursing a bruised ego at what he saw (accurately, by all accounts) as blatant disrespect from his fellow American officers, many of whom openly stole credit for his successes on the battlefield.

Knowing all of this, Andre would have to tread carefully. He knew that as a walk-in, Arnold would likely be nervous, and despite his outward confidence, might balk and walk out. Andre would have to take advantage of the rapport and friendship that he had established with Arnold years earlier, never taking for granted that the man’s freedom and possibly his life was on the line, recognizing that, when the reality of that hit him, Arnold might regret his decision. The major would likely have deferred to the general, mostly to stroke the latter’s ego, while carefully establishing and maintaining control of the meeting and the relationship.

At some point in the conversation (if he followed today’s protocol and definition of a recruited asset), Andre would have asked Arnold what it was he wanted in return for the surrender of West Point. In this case, he wanted £20,000 (approximately $1.1 million today). As stated earlier, and in a move common to today’s recruitment of a hard target (i.e., a North Korean national), negotiations over a final sum would take months. In today’s world, and by today’s standards, Andre would have known that. Nevertheless, Arnold agreed to pass plans to the fort to Andre, and after a series of meetings and correspondence, did so.

It is here that flaws in Andre’s tradecraft become evident. He would have known (or should have) the limitations of the operation and his asset. Arnold, although a brilliant general, was driven by ego. At any time, wanting to impress either his wife or another officer, Arnold could have easily revealed the plan. Andre should have, if he had time, vetted the information that was being passed to him. For all he knew, the walk-in could have been a false-flag ploy designed to draw out Andre or others in his network. He could have established a dead drop or other form of impersonal communication in order to pass messages or information. And this last oversight is what would cost Andre the operation, his freedom, and ultimately his life.

Opting to personally transport the plans provided by Arnold, Andre set out by horse, accompanied by one Joshua Hett Smith, who also provided the safehouse (his own family home) for Andre and Arnold to hold their clandestine meetings. Andre was disguised in clothes worn by commoners and bore a passport allowing him to travel under the name John Anderson. In his stocking, he foolishly held six handwritten notes detailing the layout of the fort. I say foolishly because it was unnecessary, as Andre’s boss, General Clinton, already knew the information (this is one time that a bit of input from HQS to the field would have been welcome).

The two rode on unchallenged until the night of September 22, 1780, when Smith (for reasons never explained) suddenly departed, leaving Andre to continue the journey alone. The next day at 9 a.m., Andre was stopped by a group of armed militiamen near Tarrytown, New York. Questions posed by the men went beyond Andre’s cover story, and in answering, he revealed that he was a British officer.

Attempts to both bribe the men and to use a pass provided by Arnold failed, and the documents on his person were discovered. In a double twist of fate, the local commander, not realizing who he held and the gravity of the situation, almost had Andre sent to West Point to be turned over to General Benedict Arnold, which would have surely allowed him to escape back to British lines. Second, and most ironically, the commander at the military headquarters where he was ultimately sent was a good friend of hanged American spy Nathan Hale, and he promptly informed Andre that he expected his fate to be the same.

General Clinton refused General George Washington’s demands that he turn over Benedict Arnold in exchange for Andre, and in return, Washington denied Clinton’s request to have Andre executed by firing squad instead of hanging. Major John Andre, brilliant military tactician who had the initial makings of a good intelligence officer, was ultimately undone by poor tradecraft and the very ego that led Benedict Arnold to walk into his office in the first place.

Unlike today’s spy game, there would be no persona non grata and expulsion from the country. Andre was hung on October 2, 1780, in Tappan, New York. His body, initially buried under the gallows where he met his fate, was re-interred in 1782, and now lies in Westminster Abbey in London.

Oh, and Benedict Arnold? Upon learning of Andre’s capture, he fled to British lines and defected. His reward for defection included pay, land in Canada, pensions for himself, his wife, and his eight children, and a military commission as a British provincial brigadier general. He was never fully trusted by the British, and eventually he moved to Canada, then back to London. His business ventures failed, and he died in 1801, his name becoming forever synonymous with even the most simple acts of treachery.