Over a week had passed since Major John Andre became the Continental Army’s prisoner near Tarrytown, New York, captured by three ragged militiamen who were probably more interested in robbing him than uncovering his intentions. For a time he had been incarcerated at Robinson House, the now defector Benedict Arnold’s former Hudson Highlands headquarters, and was eventually taken to the main American camp at Tappan, New York. There, Andre awaited his trial as a spy and eventual fate.
During his time held as a prisoner in Tappan, Andre accumulated an impressive group of intrigued and sympathetic followers, including Alexander Hamilton. Later describing his impression of the British officer to Colonel John Laurens, Hamilton wrote,
There was something singularly interesting in the character and fortunes of André. To an excellent understanding well improved by education and travel, he united a peculiar elegance of mind and manners, and the advantage of a pleasing person. ’Tis said he possessed a pretty taste for the fine arts, and had himself attained some proficiency in poe[try], music and painting. His knowle[d]ge appeared without ostentation, and embellished by a diffidence, that rarely accompanies so many talents and accomplishments, which left you to suppose more than appeared. His sentiments were elevated and inspired esteem. They had a softness that conciliated affection. His elocution was handsome; his address easy, polite and insinuating.
Andre’s “elegance of mind and manner” was not enough to save him from the gallows, however, and on September 29, 1780, he was sentenced to be hanged by a board of fourteen American general officers. No witnesses were called to the stand. Andre’s previously written confession, and his admission that he had not entered American lines under a flag of truce was enough for the decision to be made. The next day, a letter was forwarded by George Washington to Henry Clinton informing him of his adjutant-general’s fate. He would be spared, however, if the British turned over Arnold. Clinton was forced to decline the ultimatum, citing military policy to his subordinates that a deserter such as Arnold must be protected. It was probably one of the most difficult responses the British general had to give in his career.
Andre’s execution was set to be carried out at 5 p.m. on October 1, but news of a delegation’s arrival sent by Clinton to make one final effort to prevent the hanging postponed it. One of the delegates, General James Robertson, met with General Nathanael Greene, and further information about Andre’s mission was forwarded to Washington. The American commander in chief would not be swayed, however. Andre would hang the next day.
After first learning of the verdict issued to him by the board, Andre accepted his fate and was determined that he would face it as a gentleman and a soldier. As part of his last order of business on earth, he penned a heartfelt letter of appreciation and loyalty to Henry Clinton. Then, he made a plea to Washington that he may be executed by firing squad like a soldier rather than hanged as a spy:
Bouy[e]d above the terror of death, by the consciousness of a life devoted to honourable pursuits, and stained with no action that can give me remorse, I trust that the request 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 the military tribunal, to adapt the mode of my death to the feelings of a man of honour. Let me hope, Sir, that if aught in my character impresses you with esteem towards me, if aught in my misfortunes marks me as the victim of policy, and not of resentment, I shall experience the operation of these feelings in your breast, by being informed that I am not to die on a gibbet.
Andre’s request was ignored. At 12 p.m., October 2, he would hang.
The morning of his execution, Andre breakfasted at Washington’s table, and as noon approached, he was led by an escort and fife and drum to the gallows, “with as much ease and cheerfulness of countenance as if he had been going to an assembly,” recalled Major Benjamin Tallmadge, who had become an admirer of the prisoner like Hamilton. He was dressed in his scarlet, gold-laced coat, and upon approaching the gallows was seen to lean back for a brief moment as if in shock to learn that his request to Washington for a military execution had been denied.
Despite this cold revelation, Andre continued on to the gallows. After struggling at first to climb the cart below the rope, he mounted it, and from the executioner’s grasp he took the noose and tied it around his own neck, then he covered his eyes with a handkerchief. The crowd surrounding him, including Maj. Tallmadge, was seen teary-eyed and sobbing. It was one more dramatic scene in the Revolutionary War, and Andre would not make it easier for anyone to witness. Lifting the blindfold, he spoke his final words, a request: “All I request of you, gentlemen, is that you will bear witness to the world that I die like a brave man.” With that, the wagon was pulled out from beneath his feet, and with one great swing and several fleeting moments, he was gone.
Major Andre’s fate was a tragedy within a tragedy. Caught up within the story of an American hero’s tragic descent towards treason, Andre became a victim of one of the darkest tales in our history. Unlike Benedict Arnold, however, whose legacy had been tarnished forever, Andre was remembered as a hero, a martyr even, by the British, and romanticized by many Americans alike. Regardless, the two men will forever be linked by history. Two-hundred and forty years later, that has not changed.
 From Alexander Hamilton to Lieutenant Colonel John Laurens, [11 October 1780], Founders Online, National Archives, accessed 1 October 2020, https://founders.archives.gov/documents/Hamilton/01-02-02-0896.
 Charles Inglis, The case of Major John Andre, adjutant-general to the British Army, who was put to death by the rebels, October 2, 1780, candidly represented: with remarks on the said case (New York, 1780), 26, https://quod.lib.umich.edu/e/evans/N13232.0001.001/1:2?rgn=div1;view=fulltext.
 Quoted in Stephen Brumwell, Turncoat: Benedict Arnold and the Crisis of American Liberty (New Haven, CT: Yale University Press, 2018), 293.