Caleb Brewster

Now, are there other characters in there that you feel like people should know a little bit more about?

I think Caleb Brewster's also, like, a cool one, um, that I think's also a little bit under-talked about, just being, like, the whaler and sh- sailing ships through the night is very, very impressive.

Yeah.

When, before we had any technology or powered boats or even s- uh, headlights, just going completely through the dark and the sound is, one, just very impressive in general.

Yeah.

They had him in the Turtle, and I wonder, you know, w- where the Turtle submarine that they used actually did fit into the story, because I know there was a Turtle, uh, but I've never really looked into whether, you know ...

And I, I don't think it was Caleb Brewster that was probably riding that across, but it was a nice-

Probably not

According to the tradition handed down in Setauket, one of that ring's signals was laundry.

When a woman named Anna Strong hung a black petticoat on her clothesline, it meant the whaleboat courier, Caleb Brewster, had come in across the sound.

The handkerchiefs she hung beside it told the network which of six coves he was hiding in, out in the open, in plain view of British soldiers who saw a farm wife doing the wash and nothing more.

Now, I'll be straight with you because that's what this show does.

The intelligence, if you could call it that, was vague, often late, and more often useless to Washington.

Now, while Scott was struggling to provide information that Washington actually found useful, Washington also received a letter from Caleb Brewster offering to gather intel from Long Island.

Um, who's Caleb Brewster? This is a new guy, isn't he?

Yes, that's a fair point.

It is a new guy.

So let's take a quick second to talk about Brewster.

All right.

Caleb Brewster was another Long Island native from Setauket and someone that Talmadge already knew.

So, Benjamin Talmadge now takes what he learned from Sackett, what was already put into place, and the foundations were already set for this, what becomes the Culper spy ring.

What is, I think, so cool about this? Three of the key figures here, Benjamin Talmadge, Caleb Brewster, and Abraham Woodhull, were high school buddies.

They went to high school.

It's not a high school like we think of, but they grew up in Setauket.

They trusted each other.

They were like – And I don't know that they were like as close as brothers, but they had that level of trust and commitment and faith in each other that they could do this.

And Caleb Brewster was certainly an ordinary guy, kind of ran a whale boat and things and was a crazy outdoorsman.

And he kind of like, I think he became more military.