250 and Counting

This day in American History, 250 years ago.

Nathan Hale’s Capture–September 21, 1776

One of the events that took place the same day of Nathan Hale’s capture is that there was a huge fire in New York that burned about a quarter of the city.

Now, the British thought that it was started by American saboteurs to prevent the city from falling into British hands. However, while that idea had come up, George Washington was under orders not to do so, and they therefore denied any responsibility. For their part, the Americans suggested that British soldiers were responsible for the fire (without orders to do so), to enable them to sack the city.

There is a third possibility out there that’s been floated, and that would be that Hale was responsible for setting the fire. However, he was across the river in Queens when he was arrested, so it’s not likely at all that he was the culprit; in fact, there’s really no evidence that arson specifically was to blame for the fire. It’s not known where it started, or whether it began in more than one place. What is known is that the weather conditions (dry and windy), plus the wooden buildings and narrow roads, made it easy for the fire to spread, and when it stopped, it was as much by wind changes as any efforts by people to put it out. (Also, a large undeveloped property acted as a fire-break.)

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September 21, 2026
Pennsylvania Writes A Constitution–September 20, 1776

The Pennsylvania Constitution turned out to have many unique qualities, but they were so good that before long they weren’t unique anymore, because so many people copied them.

That’s not to say that everything about the Pennsylvania Constitution was unique, or even original. For instance, the document begins with a Declaration of Rights that was lifted directly from Virginia.

Regardless, there were some radical ideas in there (for that time), which clearly demonstrated that some of the authors had a little bit of an ax to grind when it came to the way things were being done up until then. Government was designed to be relatively weak, in the sense that it was difficult for any one entity to seize power. Decisions were made by one body and they were largely carried out by another. Veto power wasn’t really a thing. And…anyone could vote? ANYONE? Yes, so long as they were taxpayers. And male. But that’s still a much bigger demographic than other states were offering the franchise to.

The committee which worked on this document presented it to the rest of the Committee of Safety (which was running things for the time being), and in a few days we’ll look at the actual adoption of the Pennsylvania Constitution and some of the people who opposed its adoption.

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September 20, 2026
Battle of the Black Hole–September 19, 1776

The Battle of the Black Hole, also known as the Battle of Coweecho River, lasted about two hours and had surprisingly few casualties, considering its location and just how fierce the fighting was.

Colonel Andrew Williamson essentially marched into an ambush in a deep gorge, and had to fight their way out. They began by using a circular formation because they found themselves surrounded. But because they were in such a tight spot geographically, they realized that the only way out is through, as the expression goes. Williamson led a bayonet charge, which drove out the Cherokees, who were low on ammunition anyway.

Four Cherokees were killed altogether, and eleven militiamen were killed, plus twenty-four men were wounded.

Interestingly, the exact location of the battle is not known, but based on contemporary accounts, historians have placed it at or near Wayah Gap in Macon County, NC. For some time there was an argument that it took place further north, in Swain County, a place called “Indian Grave Gap.” But given the militia groups’ respective destinations as they moved, this location doesn’t make sense.

The fact is, much of the correct information for this battle had to be painstakingly teased from contemporary reports. At one point it was thought that it was General Rutherford’s men who had fought the battle, but that was based on a single article written nearly a hundred years later. Furthermore, that article was based on sketchy research.

So the Battle of the Black Hole was brief, it was relatively bloodless, and it was the last battle in the Cherokee-American War that would take place in North Carolina, though many more were to come in other states.

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September 19, 2026
Washington’s Report–September 18, 1776

Washington’s report to Congress regarding the events at Harlem Heights a couple of days earlier didn’t pull any punches with regard to how badly his army was beaten, or what mistakes he and his men might have made.

It didn’t always make for cheerful reading in Congress, but at least they knew what they were up against. They knew they weren’t getting whitewashed “Everything Is Just Peachy” reports from someone afraid of dealing with Congressional fallout.

And fortunately, Washington’s report in this case was a mixed bag of bad luck, extraordinarily good luck, unfortunate timing and the plain difficulty of defending an island that had so much coastline within sight of adjacent coastline (because Manhattan is surrounded by rivers, not oceans). New York ended badly for the Continental Army, but there were multiple times that it could have ended so much worse.

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September 18, 2026
Langdon Cheves–September 17, 1776

Langdon Cheves had a bit of a rough start in life, but he managed to pull himself up and become quite the influential man in the early 1800s.

Despite the fact that few people have heard of him, Cheves was an active member of the House of Representatives, and managed to make the best of bad situations. When the 1810 embargo on European goods had the effect of collapsing rice and cotton prices, Cheves was able to channel the voters’ dissatisfaction into returning him to Congress. He was considered a War Hawk as 1812 rolled around and still managed to get re-elected.

Cheves was in the House of Representatives when Henry Clay was appointed Speaker, but while they generally followed similar attitudes, Clay and Cheves had a falling out over the seizure of merchants’ bonds during the War of 1812 and he found himself stripped of all committee assignments, Unfortunately for Clay, when he was asked to negotiate peace with Britain in 1824 he had to resign his position, and Cheves found himself elected Speaker. Cheves essentially went from Worst To First in the space of a year.

After leaving Congress, Cheves returned to his law practice but found himself appointed the presidency of the Bank of the United States, a position he held for longer than he’d planned because the Board of Directors had a hard time finding his replacement when he wanted to retire. After leaving the bank, he returned to South Carolina to become a rice planter and continued to engage in public debate, at one point arguing against South Carolina seceding from the Union unilaterally, believing in Southern unity.

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September 17, 2026
Battle of Harlem Heights–September 16, 1776

While it didn’t change the result in New York, the Battle of Harlem Heights was a tactical win for the Continental Army, and a boost to morale as well.

It was the Continental Army’s first true victory since Lexington and Concord, and after the demoralizing loss at Kip’s Bay only a day earlier, demonstrating that these soldiers (who were still little more than ordinary citizens) could, in fact, stand up successfully to the mightiest fighting force in the world.

Harlem Heights is a neighborhood to the west of Harlem, and nowadays is called Morningside Heights. A cynic would suggest that the neighborhood changed names in the 1890s so that Columbia University wouldn’t have to be associated with a predominantly black neighborhood, but to be fair the neighborhood was also known as Cathedral Heights because of the presence of St. John the Divine Cathedral.

At any rate, the neighborhood is definitely worth a visit. There are a few historical plaques around Columbia University, and if you like visiting cathedrals, St. John is definitely worth your while. Grant’s Tomb can also be found in that area, and if you’re a fan of the TV show Seinfeld, you will be thrilled by what you find at 112th St and Broadway. That’s all I’m sayin’.

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September 16, 2026
Battle of Kip’s Bay–September 15, 1776

Calling it “The Battle of Kip’s Bay” may actually be overstating it a little bit; there were 500 militamen from Connecticut in the area when the British landed, and their defenses were blown away almost immediately, after which they panicked and ran.

But I tell you all about that in the episode. This is my chance to tell you a related story, and nobody knows whether it’s true.

If you look at today’s artwork, you’ll see a piece of a map and an estate called Inclenberg, about where modern-day Murray Hill can be found. Kip’s Bay is just out of frame to the right. Inclenburg was owned by the Murray family (hence the neighborhood name), who were a family of Quaker merchants who owned a wharf and a fleet of ships at the base of Wall Street.

Now, the story goes that the original plan was for the British to march across Manhattan, west to east, in order to cut off Washington’s army. As I note in the episode, about a third of them were still to the south in the city and would therefore be trapped and stranded. Then, once they were divided, the British would pursue the rest of them to the north, in Harlem Heights.

What’s known as a fact is that the British did not complete their traversing of the island; they stopped somewhere around Inclenberg. The legend part of this story is that when they got to Inclenberg, Mary Murray, the socialite who ran the estate, and two of her lovely daughters came out to greet General Howe and his commanders and offered them some afternoon tea.

Howe and his officers had a wonderful afternoon of hospitality, with tea and entertainment by the girls (singing, ya pervert), and the finest Madeira wine in New York City. In the meantime, Major Aaron Burr led the separated group of troops up through the western side of the city to Harlem Heights, and relative safety.

It’s really more likely that Howe simply stopped while waiting for more forces to arrive, and that’s the story I tell during the episode. But it’s a fun story, and it is known for sure that General Putnam’s men did escape what would have been certain capture by the British, who had to be absolutely apopleptic to learn that so many soldiers had escaped yet again without their knowing about it.

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September 15, 2026
Word From Congress–September 14, 1776

Washington was on the brink of retreating from New York City, but he was getting pushback from some of his generals regarding how it should be done.

Fortunately for him, this Gordian Knot was cut by a letter arriving from John Hancock on behalf of the Continental Congress.

Nathanael Green and William Heath weren’t necessarily in agreement with Hancock’s recommendations, but orders are orders and everyone prepared to move out based on those.

But about a week later, something happened to render part of those orders moot.

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September 14, 2026
Suspicious Movements–September 13, 1776

When Patriot forces saw four ships moving into Bushwick Creek, it was ominous but probably not a huge surprise, given that the British already held Brooklyn. They put up largely token fire from their own strongholds and that was pretty much that.

Washington knew that Manhattan was next, but it wasn’t clear how the attack would come, or from where specifically, but he’d already begun the work of getting people and materials out of town, so it probably wasn’t much more than a distraction for him.

In fact, it was a distraction and a diversion, as we’ll learn in a couple of days. Whether it was strictly necessary is another question.

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A quick note on today’s artwork: Robert Clevely was a marine artist who was an eyewitness to the landing on Kip’s Bay. I figured it was worth mentioning because so many of the art pieces I wind up presenting here aren’t necessarily contemporary to their subjects. But this one is someone who was actually there.

September 13, 2026
To Stay, Or Not To Stay?–September 12, 1776

George Washington’s Council of War finally got to meet on this day in 1776, to figure out what happens next.

The Battle of Long Island was a rout for several reasons. In addition to the Continental Army being outnumbered by roughly two-to-one, there was poor communication and a couple of tactical errors. And the only reason more soldiers weren’t captured or killed was because poor weather prevented the British from figuring out that they were escaping across the East River until it was far too late.

So, as any good soldier would, Washington took a moment out to seek advice from his Council of War. Nathanael Greene recommended just getting out of town and regrouping elsewhere, but he also suggested burning the city down to keep it out of British hands. Washington already knew that Congress didn’t like the burning thing.

Most of Washington’s council recommended leaving the city, but Washington still wanted to ensure that some portions of the city were fortified and made appropriate plans. Unfortunately those plans fell apart rather quickly, as we’ll soon learn.

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September 12, 2026