Head of British Secret Service in America

In 1779, André became adjutant general of the British Army in North America with the rank of major. In April of that year, he took charge of the British Secret Service in America. By the next year (1780), he had briefly taken part in Clinton's invasion of the South, starting with the siege of Charleston, South Carolina.

Around this time, André took over secret British communications with U.S. general Benedict Arnold. Arnold was a much-admired field general who had been wounded twice in battle, and was considered an American hero for his actions at the Battle of Saratoga. He was also impetuous and hotheaded. Arnold had become bitter about the decline in his financial fortunes caused by the war, and the reluctance of the Continental Congress to grant him the promotions he believed he deserved.

Arnold's Loyalist wife, Peggy Shippen, was one of the go-betweens in the correspondence with André. Arnold steadily provided the British with vital intelligence on American troop movements and Washington's strategy. His ultimate goal was to be the key player in helping the British achieve such a knock-out blow against the Colonials that he would handsomely rewarded. In pursuit of this plan, he carefully maneuvered his way into the command of the critical Continental Army fortifications at West Point, secretly promising to surrender them to the British for £20,000 (approximately £3.62 million in 2021).^[5] Possession of the forts at West Point would deliver to the British effective control of the entire vital Hudson River waterway, and might very well serve as the death-blow that doomed the Continental cause.

U.S. general Arnold and British major John André plotted the surrender of West Point at this spot on the shore pathway south of Haverstraw, New York, in the historic Dutchtown area. Today this is part of Hook Mountain State Park

As the summer of 1780 ended, Arnold had at last taken command of West Point, and was in a position to facilitate a British takeover of the forts. Major André traveled up the Hudson River on the British sloop-of-war HMS Vulture to meet Arnold. The presence of the warship on the upper Hudson, close to Patriot territory, was first discovered the following morning by two American privates, John Peterson and Moses Sherwood, on 21 September.^[6][7] From their position at Teller's Point, they attacked HMS Vulture with rifle and musket fire. Seeking greater firepower, Peterson and Sherwood headed to Fort Lafayette at Verplanck's Point to request cannons and ammunition from their commander, Colonel James Livingston.

During this pause in the shooting, a small boat furnished by Arnold was steered to the Vulture by Joshua Hett Smith. At the oars were two brothers, tenants of Smith, who reluctantly rowed the boat 6 miles (10 km) on the river to the sloop. Despite Arnold's assurances, the two oarsmen sensed that something was wrong. None of these men knew Arnold's purpose or suspected his treason; all were told that the purpose was to do good for the American cause. Only Smith was told anything specific, and that was the lie that it was to secure vital intelligence for the American cause. The brothers finally agreed to row after Arnold mixed threats of arrest with a bribe of fifty pounds of flour for each man. They picked up André from the Vulture and brought him ashore, where Arnold was waiting.^[8]

The two men conferred in the woods below Stony Point on the river's west bank until nearly dawn on September 22. Then, instead of returning to the Vulture, André decided to continue their conversation, and with the sun coming up, he and Arnold rode several miles to Smith's house (later named Treason House) in West Haverstraw, New York, owned by Thomas Smith, Joshua's brother.

That same morning, the Americans on Teller's Point, under the command of Livingston, launched a two-hour cannonade on HMS Vulture using heavy guns.^[9] The sloop, trapped by the Hudson's tidal currents, sustained many hits before it was finally able to escape downriver. The retreat of the British sloop stranded André on shore.^[10][11][12]

Taken into custody

Arnold persuaded André that his best option for returning to British territory was to travel overland, which meant that he would need to take off his British officer's uniform and put on civilian clothes. He bore six papers hidden in his stocking, written in Arnold's hand, that showed the British how to take the fort. In the event that André was met by American sentries, Arnold gave him a passport allowing him to travel under the name John Anderson. Arnold departed to return to his home, and Joshua Hett Smith escorted André a few miles north, where the two men crossed to the east side of the Hudson at King's Ferry^{[lower-alpha 3]} André, who had expected to travel to and from the meeting by ship while dressed in full uniform, was now traveling by road, in civilian disguise. He was deep behind enemy lines, and risked arrest as a spy.

After spending the night in a local home, the two men continued on to the Croton River, the southernmost edge of the American lines. Here Smith left him and André continued south in hopes of coming into contact with one of the Loyalist bands who marauded through Westchester County.^[13]

The Joshua Hett Smith House in 1909

André had been warned to keep inland, but instead he shifted west until he was riding down the Albany Post Road, which follows the edge of the Hudson.^[14] He rode on safely until 9 a.m. on 23 September, when he arrived at the crossing of a stream known as Clark's Kill^{[lower-alpha 4]} (since renamed the André River). Here three young men: John Paulding, Isaac Van Wart and David Williams stopped him.^[15][16]

André believed that these three were Loyalists because Paulding was wearing a Hessian soldier's uniform. Paulding had himself escaped from a British prison only days earlier, aided by a sympathetic Loyalist who provided him with the uniform. "Gentlemen," André said, "I hope you belong to our party." "What party?" asked one of the men. "The lower party", replied André, meaning the British, whose headquarters were to the south. "We do" was their answer. André then declared that he was a British officer who must not be detained. To his surprise, Paulding informed him "We are Americans," and took him prisoner.^[17] André then tried to convince the men that he was a US officer by showing them the passport Arnold had provided to him. But the suspicions of his captors were now aroused; they searched him and found Arnold's papers and the plans for West Point hidden in his stocking. Only Paulding could read and Arnold was not initially suspected. André offered them his horse and watch to let him go, but they declined.

André later testified at his trial that the men searched his boots for the purpose of robbing him. Whether or not this was true, the laws of New York State at the time permitted the men to keep whatever booty they might find on a Loyalist's person. John Paulding suspected that André was a spy and took him to Continental Army's frontline headquarters in Sands Mill (in today's Armonk, New York,^[18] a hamlet within North Castle situated on the Connecticut border of Westchester County).

The capture of John André, 1845 lithograph

At first, all went well for André: the post commandant, Lieutenant Colonel John Jameson, unsure as to Arnold's role in the spy's mission, decided to send André back to Arnold's home and headquarters close to West Point. But Major Benjamin Tallmadge, head of Continental Army Intelligence, arrived and was considerably more suspicious of Arnold's part in the episode. He persuaded Jameson to send a rider to bring the prisoner back.^[19]

Jameson sent General George Washington the six sheets of paper carried by André, but he hedged his bets about Arnold; Jameson knew that his own career would be in jeopardy if he treated Arnold with suspicion and Arnold was absolved of guilt. In place of André himself, he sent Arnold a letter informing him of André's capture. Arnold received Jameson's note while at breakfast with his officers, made an excuse to leave the room, and rushed upstairs to confer with his wife. Soon after, he made his escape to the Hudson, where he boarded his personal barge and ordered the crew to row him to the Vulture, which had returned to its northerly position on the river. Arnold turned himself over to the British commander of the ship, who promptly sailed for New York City to deliver Arnold to General Clinton.

An hour or so later, Washington arrived at West Point with his party; he had not yet received Jameson's letter or the incriminating documents, and as yet knew nothing of Arnold's betrayal or his flight. Washington was disturbed to see the stronghold's fortifications in such neglect, part of the plan to weaken West Point's defenses. Washington was further irritated to find that Arnold had breached protocol by not being present to greet him. Finally, several hours later, Washington returned to Arnold's home and headquarters on the eastern side of the Hudson, where the documents taken from André were presented to him. Instantly grasping the meaning and significance of the papers, Washington quickly sent men to try to intercept Arnold, but it was too late.^[20]

André, meanwhile, was held in South Salem, New York, and then briefly at Arnold's home, before being transferred across the Hudson to the Army headquarters in Tappan, New York. According to Tallmadge's account of the events, he and André conversed during the latter's captivity and transport. André wanted to know how he would be treated by Washington. Tallmadge had been a classmate of Nathan Hale while both were at Yale, and he spoke to André of Hale's capture, and what Tallmadge considered to be Hale's cold-blooded execution. André asked whether Tallmadge thought the situations similar; he replied, "Yes, precisely similar, and similar shall be your fate."^[21]

Trial and execution

Self-portrait by André, drawn on the eve of his execution

Washington convened a board of senior officers to investigate the matter. The trial contrasted with Sir William Howe's treatment of Hale some four years earlier. The board consisted of Major Generals Nathanael Greene (presiding officer), Lord Stirling, Arthur St. Clair, Lafayette, Robert Howe, von Steuben, Brigadier Generals Samuel H. Parsons, James Clinton, Henry Knox, John Glover, John Paterson, Edward Hand, Jedediah Huntington, John Stark, and Judge Advocate General John Laurance.

André's defense was that he was suborning an enemy officer, "...an advantage taken in war..."^[22] André told the court that he had neither desired nor planned to be behind American lines, but had been summoned ashore by Arnold and stranded there accidentally when the Vulture sailed away. He also asserted that, as a prisoner of war, he had the right to escape in civilian clothes. On 29 September 1780, the board found André guilty of being behind American lines "...under a feigned name and in a disguised habit..." and ordered that "Major André, Adjutant-General to the British Army, ought to be considered as a spy from the enemy, and that agreeable to the law and usage of nations, it is their opinion, he ought to suffer death."^[22]

Sir Henry Clinton, the British commander in New York, did all that he could to save André, his favorite aide. But in their written negotiation, Washington demanded that in exchange for André, Clinton must give the Americans the traitor Arnold, who was now under British protection in New York City. Clinton personally disliked Arnold, but declined to hand him over to his former compatriots.

From the time of his arrest, André endeared himself to American officers, some of whom lamented his death sentence as much as the British. Alexander Hamilton in particular was thoroughly charmed by the young and erudite British spy. "He united a peculiar elegance of mind and manners, and the advantage of a pleasing person," he wrote.^[23] As the execution date approached, André appealed to Washington to be executed as a combat officer by being shot, rather than hanged as was customary for spies. "I trust that the request that I make to your Excellency at this serious period, and which is to soften my last moments, will not be rejected. Sympathy towards a soldier will surely induce your Excellency and a military tribunal to adapt the mode of my death to the feelings of a man of honor." Washington refused his request.^[24]

John André was hanged as a spy at Tappan, New York on October 2, 1780.^[25] André, according to witnesses, placed the noose around his own neck and tightened it.^[26][27]

André's hanging

The day before his hanging, André drew a likeness of himself with pen and ink, which is now owned by Yale College. A religious poem was found in his pocket after his execution, written two days beforehand.^[28]

Lafayette was reported to have wept at the execution of André. Alexander Hamilton wrote of him: "Never perhaps did any man suffer death with more justice, or deserve it less."