250 and Counting

This day in American History, 250 years ago.

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
The Staten Island Peace Conference–September 11, 1776

The Staten Island Peace Conference was a bust almost from the beginning. Not because the sides were so opposed, but because one side didn’t have the authority to do any real negotiation.

John Adams, Edward Rutledge and Benjamin Franklin had to row over from Perth Amboy, New Jersey to get to the Totten House, which is near the southernmost tip of New York State, on Staten Island. At the narrowest point I could find from the vicinity of the house, that’s nearly a half-mile across the mouth of the Arthur Kill River where it opens into Raritan Bay and ultimately the Atlantic Ocean.

Unfortunately, Admiral Howe was so limited from a diplomatic standpoint that there wasn’t a lot he could do at that point, so after a few hours they broke up and the delegation was allowed to return to New Jersey. The war would continue for another severn years before concluding.

In retrospect, we have multiple attempts for Admiral Howe to meet with George Washington, which failed on the basis of protocol (Howe wouldn’t refer to Washington as a General), so now we have to wonder what direction negotiations would have gone had one of those attempts succeeded. Would things be different, or would it wind up the same, and the events of today be obviated? If a meeting in July had ended in no agreement, would John Sullivan even have been paroled to go to Philadelphia and present the plan?

I’ll leave that for you to chew on. In the meantime I’m still sounding pretty sultry, so enjoy that.

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September 11, 2026
More Bad News–September 10, 1776

General William Heath was around for the battle at Lexington and Concord, but you may remember him from our episode from just a few days ago.

He was already a Brigadier General in Massachusetts before Lexington & Concord, and as the siege in Boston started, he worked at training the troops. When the Continental Army officially formed, he retained his title and was promoted to Major General in August 1776.

Unfortunately (as Mike notes), George Washington didn’t think much of him and kept him largely sidelined. And the one time Washington did ask him to do something important, it didn’t go well at all.

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September 10, 2026
The Peace Delegation–September 9, 1776

First off, my apologies to you, and to Mike (because it was his episode), for not double-checking that yesterday’s episode was actually loaded into the feed. I’ve been fighting off a ridiculous sinus infection and I think my medication had me woozy.

On the bright side, I’m probably sounding extra sexy in today’s episode because my head still feels like a brick.

Yesterday’s show should be in your podcast feed now, though, along with this one.

Today we have a trio of delegates headed to New York to attempt peace talks with the British. Meanwhile back in Philadelphia, the Congress officially declares that our country’s name is the United States of America. Check out the story behind that.

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September 9, 2026
Nathan Hale’s Fateful Decision–September 8, 1776

There are lots of images of Nathan Hale that have him looking like a middle-aged fellow, and then there are others that have him looking like some kind of idealized young man, with a prominent jaw and youthful good looks.

The fact is, nobody today is 100% sure what he looked like, because no contemporaneous images of him have been found. The best we have is a description written by a fellow soldier of his, Lieutenant Elisha Bostwick. Bostwick wrote:

I can now in imagination see his person & hear his voice—his person I should say was a little above the common stature in height, his shoulders of a moderate breadth, his limbs strait & very plump: regular features—very fair skin—blue eyes—flaxen or very light hair which was always kept short—his eyebrows a shade darker than his hair & his voice rather sharp or piercing—his bodily agility was remarkable. I have seen him follow a football and kick it over the tops of the trees in the Bowery at New York, (an exercise which he was fond of)—his mental powers seemed to be above the common sort—his mind of a sedate and sober cast, & he was undoubtedly Pious; for it was remark’d that when any of the soldiers of his company were sick he always visited them & usually Prayed for & with them in their sickness.

Hale was twenty-one years old in 1776, so the images of him as an older man are almost certainly incorrect. The statue used in today’s cover art is one of several copies cast in 1912 from a sculpture by Bela Pratt. (Baltimoreans note: Bela Pratt was a distant cousin of Enoch Pratt, the man who founded the city’s libraries.) In addition, Pratt’s sculpture was the model for two postage stamps issued in 1925 and 1929.

We know nowadays that Hale’s efforts to infiltrate the British didn’t work out very well, and Mike and I will return to his story in a few days to tell you specifically how it shook out, and a long-standing controversy over his last words—what did he say, and how did he say it?

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September 8, 2026
All Under Heaven Is Chaos–September 7, 1776

…but the situation was not excellent, for the American side, anyway.

George Washington got a wake-up call in the form of a letter from Congress. In that letter he was told that it was not a good idea to burn down New York City; what’s more, they weren’t quite so invested in his holding the City as he thought they were. This was a good news/bad news situation for him, since he knew that strategically, the British occupying New York had the potential to be a huge problem, especially if they were able to take the entire Hudson Valley.

But even if they didn’t, having one of our biggest and busiest ports was going to create a lot of headaches, regardless of what was supposed to be moving in or out of the city.

Meanwhile, we have Ezra Lee making his first attempt at genuinely deploying the Turtle submersible. The currents plus the darkness made maneuvering very difficult, and while he did get close enough to Admiral Howe’s ship to stick the explosive charge to it, the spear he used couldn’t penetrate the hull enough to stick. In recent years it’s thought that he tried to pierce the hull near the rudder, which had an iron plate on it; another theory involved the recent use of copper on ships’ bottoms, but this copper was quite thin and would have been easily pierced.

Lee made one more attempt with the Turtle, on October 6, but that try also failed. The Turtle was lost less than a week later when the sloop serving as her tender was sunk by British ships. Who knows? Maybe there are still pieces of her in the Hudson River.

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September 7, 2026
Redrawing Maryland Maps–September 6, 1776

I’ve brought this up in the past, but Maryland appears to have an extraordinary grasp of its own history, even when it comes to naming Maryland counties.

As Mike notes today, Maryland has the first two counties established by local representatives, and the first counties named after popular Americans. But even in Maryland, when the names come from old-world aristocracy, it’s not always easy to draw the lines from A to B. For instance, the colony of Maryland was established by Catholic settlers in what became St. Mary’s City, but the colony (and later state) name derives from Queen Henrietta Maria, the wife of King Charles I (and namesake of Charles County).

My favorite bit of trivia about Maryland counties (leave me alone, I know what that sounds like) is Anne Arundel County, named after the wife of Cecilius Calvert, whose last name actually had a second L (“Arundell”). Cecilius Calvert was the second Lord Baltimore. And now you know where Cecil County, Calvert County and Baltimore County and Baltimore City got their names.

(I list the county and city separately because they’re separate regions politically and geographically. Baltimore County surrounds the city on three sides.)

But getting back to Anne Arundel: unless I’m mistaken, and so far in my casual research, I’m not, Anne Arundel County is the only county in America that has someone’s first and last name in it. Beat that with a stick.

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September 6, 2026