The Bank Where an American Spy Was Executed
On Scaffolds and Scaffolding.
There are a lot of incongruities in New York that can run the gamut from charming to quirky to offensive: old buildings nestled between glass towers, objectively shocking wealth inequality, the most chic and glamorous person you’ve ever seen delicately picking their way through mountains of trash bags. Even amongst those, there’s still something startling about the corner of 65th and 3rd, where the mythic crashes into the prosaic.
On an unassuming corner of the upper east side on the wall of a TD Bank that looks like every other TD Bank is plaque marking the spot were Nathan Hale was hanged by the British in 1776, one of the American Revolution’s earliest martyrs swinging by an ATM.
Before he was a name on a plaque and a towering figure in our national origin story, Hale was born in Coventry, Connecticut1 in 1755, the sixth kid in a quite Protestant family.2 He went to Yale, where he was in a secret society/frat/book club with Benjamin “Spymaster of the Culper Ring” Tallmadge, and then went to work as a schoolteacher in New London. After Lexington and Concord, he volunteered and served in the Connecticut Seventh Regiment. He was young and didn’t have military experience, but he had gone to Yale so he was quickly made a captain.3 His regiment was dispatched to the Siege of Boston in 1775 and the Battle of Brooklyn in August of 1776, but far enough away from the front lines that he was frustrated at not feeling fully of use. Washington retreated to keep Howe from ending the revolution then and there and Hale requested a transfer. He was assigned to Lieutenant Colonel Thomas Knowlton’s regiment. In the wake of the defeat in Brooklyn, the American army was looking for intel from behind enemy lines. Hale volunteered immediately.
It's worth underlining that Hale volunteering also meant he was not Knowlton’s first choice – that had been an officer named James Sprague who refused the assignment.4 Here’s the thing about that: Hale was maybe not a great spy.5 By all accounts, he had the bearing of a solider and couldn’t really disguise it. He was forthright and honest, which is an admirable virtue unless lying is an integral part of your job.6 By all accounts, he did excel at gathering and retaining information but you really need both halves of the equation.7 A friend named William Hull had even tried to talk him out of the gig on account of the whole “your life will depend on lying well” thing but Hale was determined.
So on September 15th, 1776 as General Howe landed a company at Kips Bay8 to take Manhattan,9 Hale set off for Howe’s Brooklyn encampment to talk to soldiers and generally make any observations he could. There wasn’t a lot of planning behind the operation, but also Hale had his Yale diploma with his real name on him and his cover was a Dutch schoolteacher but he may not have spoken Dutch, which is kind of like getting caught out by a bouncer because you give your real birth year and not the one on the ID you’re using10 only the stakes are life and death rather than underage drinking. Long Island Sound was rough (metaphorical) turf11 to sneak into, so Hale had been dropped off in the middle of the night by the ship The Schuyler12 which makes sense but also reads pretty suspicious to anyone who witnesses it, so word got to British counterintelligence pretty immediately. By September 19th, what should have been the penultimate day of his mission, he’d already been made and was in the sights of Robert Rogers and the Queen’s Rangers.
Rogers was born and raised in New England13 and made an impression and a mix of reputations14 fighting in the French-Indian War as a ranger. He made a popular splash but also a lot of professional rivals and wound up in debt, largely because of paying his troops and laying out for expeditions out of pocket but booze may not have helped. He was in and out of favor on both sides of the Atlantic, depending on who was in charge at any given time. When tensions mounted and a revolution seemed to be on the way, Rogers made approaches to both sides. Each seemed moderately leery but the British bit first so, in 1776, Rogers was working in New York looking for information on the movements of the patriot army and British deserters. He trailed Hale from where he’d had word of a late night solo disembarking and found him making notes. He approached Hale at dinner at the tavern he was staying in, convinced him they were on the same side, and that was basically that. Rogers invited Hale for breakfast with likeminded compatriots15 and got Hale to confess again, this time in front of witnesses.
That night, September 21st, the Great Fire of 1776 broke out in British-occupied lower Manhattan. With temperatures running high,16 Hale was arrested and brought to General Howe, who had set himself up at Mount Pleasant, the summer house of a merchant named James Beekman. Mount Pleasant was a summer house the way Peter Stuyvesant’s orchards were north of the city as he knew it: it stood at what’s now 51st and 1st. Beekman was enough of an American patriot and high society figure that Washington had swung by the house by during his retreat up Manhattan after the Battle of Brooklyn and advised him to flee ahead of the British. By the time Howe made it up to Turtle Bay, it was empty and he made himself at home.
So this was the scenic spot with East river access that Rogers brought his captive, who was executed the next day without a trial on the 22nd.17 Hale’s last night was spent in Mount Pleasant with a British engineer and aide de camp to General Howe named John Montresor, going over the notes he had taken and also making whatever kind of chitchat the situation allowed, as Montresor felt bad that Hale had been denied his request to speak with a clergyman or have access to a Bible.18 He wrote in his diary19 of Hale’s calm and integrity and certitude in the righteousness of his cause and he also wrote of where the hanging took place.
That last bit isn’t as obvious as it sounds. For decades it had been assumed Hale was hanged downtown near City Hall, but Montresor referenced a bar near Royal Artillery Park off Post Road about a mile from Beekman’s place/Beekman Place. The Post Road was exactly what it sounds like: it was a mail route based on Lenape roads that ran from Park Row up the east side of Manhattan, swung west then up to the Bronx and on to the Boston via New Haven. There were mile markers throughout the city,20 set up partly under Ben Franklin’s tenure as Post Master to make it easier to determine postage but also serving to make it easier to interpret Montresor’s notes.21 The “where” isn’t the only question about Hale’s execution that has us snooping through British diaries like a brother in a teen comedy: there’s also the question of what he said outside this bank on the upper east side. Years after, Montresor would meet with Hale’s friend William “I Hate To Say I Told You So, But I Did Say Maybe You’d Be Very Bad At Spying” Hull and Hull points to Montresor’s account as the origin of Hale’s final words being “I only regret that I have but one life to lose for my country.” Two things about that. One, it’s paraphrasing a play: Joseph Addison’s 1713, Cato, A Tragedy which would have been known to Hale and his friends and included to the lines, "How beautiful is death, when earn'd by virtue! Who would not be that youth? What pity is it that we can die but once to serve our country." Hale could have referenced it or misremembered it, either under an apple tree with a noose around the neck or when making small talk with Montresor the evening before while writing letters to his family Montresor never actually delivered. The second thing is that Montresor wasn’t the only Brit with a journal to watch Hale die:22 an officer named Frederick MacKensie, after also praising Hale’s calm and composure, did not write of any statements of regret but said that Hale encouraged any patriots watching to be ready to meet death in whatever shape he came. He may not have been a very good spy, but he certainly wasn’t a hypocrite.
There wasn’t much of an announcement made immediately after Hale’s death. There was some concern about lowering morale when things weren’t going well already, but there’s also something to be said for the speed at which everything unfolded that September and the degree to which the city itself was on fire both literally and metaphorically. Hale was mentioned in Hannah Adams’ 1799 History of New England. His story was burnished and amplified by historian George Dudley Seymour, who really made Hale into folk hero and national martyr he is today. In 1893, the Sons of Liberty23 unveiled a statue of Hale outside City Hall, which was still assumed to be the place of his execution. Modern security protocols have left the part of the park where his statue stands inaccessible to the public by fence, chain and barricade. This means Hale’s statue is a better kept secret now than his identity was behind enemy lines as a spy which is a real sad trombone of a womp womp.24
That’s how an in-way-over-his-head twenty-one year old ended up being memorialized by the door to a bank in the storefront of a condo. I don’t think many of us are especially surprised when we learn the heroes given to us as children are not as good or as good at their jobs as we once thought, but maybe with Hale that’s only partially correct.25 There are, after all, worse traits a folk hero could have than bravery and being very bad at lying. In a way, he got his likely-apocryphal wish, as he gave both his real life and a second, more fanciful rendering of it for his country.
As I’m sure you noticed (because it’s amazing!!), this week’s newsletter features a comic commissioned from artist Emily Zilber. Emily Zilber is a cartoonist, writer, and illustrator. Her work has been published through MUTHA Magazine and the Sequential Artists Workshop. Emily lives in Philadelphia with her husband, identical twin daughters, and two obscenely furry cats. Find more at www.emilyzilber.com and @emilyzilberdraws.
About six miles north of Andover and a half hour drive east of Hartford.
Saying “quite Protestant” and “Connecticut” might be redundant in the eighteenth century, considering it was established by people worried that Massachusetts had gotten too chill.
It doesn’t sound great when you type it out, but worse people have gotten further based solely on going to Yale, which also doesn’t sound great.
Probably why James Sprague lived to 84 years old, survived by his wife and their seven children.
When you think about, maybe the first sign was how famous he is.
Like how pacifism is an admirable ideology unless you happen to be the commander of the Army of the Potomac during the Civil War. Ahem, McClellan.
If you’re looking for an exceptional spy, have you heard of Mary Richards Bowser, a key part of the Elizabeth Van Lew spy ring? You may not have – she was really good at hiding in plain sight. Also, she was a Black woman, so you can be reasonably assured her name isn’t lifted the way her astounding acts deserve to be. That’s a different story, however, a different war, and a different state.
Kips Bay being invaded by an army of red coats actually makes Howe’s landing the first SantaCon, but maybe with less vomiting.
A feat not repeated until the Muppets.
I’ve heard, anyway. I wouldn’t know or can’t remember, depending who’s asking.
Surf and turf?
A pretty familiar street and town name to a lot of people who have spent time in the city or upstate or who have seen Hamilton.
Massachusetts and New Hampshire, respectively, lest it sound like I’m the kind of New Yorker who can’t see north of Westchester.
More bold than consistently reliable, might be the best summation.
Likeminded for Rogers, anyway.
Pun intended.
There were some loose accusations that he’d burned New York in retribution for Washington’s loss, but he was already under Rogers’ observation on the other side of the river by then.
Howe harsh.
Which ended up in the collection of the New-York Historical Society, so I guess when America took back New York, it also snagged some journals as a bonus.
Park Row and Bowery was 0 and they moved north, so mark 3 was in what’s now Madison Square Park, near the statues of Roscoe Conkling and Chester A. Arthur.
Leave it to our nation’s sluttiest founder to keep things easy, amirite?
Seems like a weird, very specific fad to me but I was also thrown when everyone was wearing cat ear headbands that had nothing to do with the Josie and the Pussycats movie, so maybe I’m just not built to be trend-forecaster.
I’m assuming by that point they were more like the Great-Grandsons of Liberty.
The Mary Washington Chapter of the DAR also erected a plaque outside the Yale Club on 44th and Vanderbilt on September 22nd, 1948—so the 172nd anniversary of his death—that states the hanging was “near this site” but that “near” is doing a lot of work. It’s sure one way to get his graduation year out from and center.
Not everyone can be Nancy Wake, after all, though it would be better if they were: she was an excellent spy and the world needs more great hats, sharp comebacks, and dead Nazis.
muppets