The Origin of Weird: Timothy Dexter

A fortune built on bed warmers, coal, stray cats, and whale bones shouldn’t exist, yet Timothy Dexter kept cashing in. We jump into the outrageous life of a leather apprentice turned millionaire who wagered on “worthless” Continental currency, shipped the wrong goods to the right places, and somehow surfaced on the winning side of almost every trade. The more he won, the bigger his persona grew—statues of himself, a gilded mansion, and a jaw-dropping stunt funeral that pushed his quest for status over the edge.

We break down the trades that made his legend. Why did bed warmers sell in the tropics? How did coal to Newcastle pay when the city was awash in fuel? What made islanders buy cats by the crate? And how did a pile of baleen turn into a corset gold rush? Along the way, we explore the infrastructure of early American trade, the fallout of Revolutionary War finance, and the way simple scarcity questions can beat the experts. Dexter’s “A Pickle for the Knowing Ones,” a punctuation-free pamphlet, adds to the spectacle—part trolling, part marketing, fully memorable.

Beneath the antics is a debate that still resonates: was Dexter absurdly lucky or quietly perceptive about markets and timing? We look at how ridicule from insiders may have pushed him toward contrarian bets, how strikes and fashion cycles became catalysts, and how audacity turned risk into headline-grabbing returns. It’s a story about arbitrage, ego, and the thin line between genius and buffoonery—told with humor, curiosity, and a clear eye for the lessons buried inside the chaos.

Enjoyed the ride? Follow the show, share this episode with a friend who loves strange history, and leave a quick review to help others discover the podcast. Got a question or a wild historical theory for us to explore next? Drop us a note—we’d love to hear it.

Transcript

Milestone And Banter

SPEAKER_04 0:15

Oh, hey there.

SPEAKER_03 0:17

Oh, hey there.

SPEAKER_04 0:18

How's it going today?

SPEAKER_03 0:19

I'm good. How are you?

SPEAKER_04 0:20

I am well. I'm Bradley.

SPEAKER_03 0:22

I'm Kate.

SPEAKER_04 0:22

This is the History Buffoon's origin of weird. I don't know if you could tell, but that was an actual trumpet. The beauty is I I said that as she was about to take a sip of her beverage.

SPEAKER_03 0:43

Well and behold, it was actually a trumpet.

SPEAKER_04 0:48

Anyways.

SPEAKER_03 0:50

So okay, so this is our 100th combined episode.

SPEAKER_04 0:58

So if you take buffoons plus origin, since we've started, this would be our hundredth released episode. So we kind of do these separately where we do the origin side and the buffoon side. But if you put them together, yes, this is our 100th episode. So congratulations. Look at us go. We made it to 100 total. Um, 101 if you include our our trailer, but I don't because why would you? But no, yeah, this is our hundredth hundredth episode.

SPEAKER_03 1:28

So well that deserves a cheers.

SPEAKER_04 1:30

Well, in a crossroom high five.

SPEAKER_03 1:32

High five.

SPEAKER_04 1:33

There we go. All right. What do you got for uh what's weird today?

SPEAKER_03 1:39

Well, we are gonna talk about Timothy Dexter.

SPEAKER_04 1:42

Timothy Dexter. I have not heard of such a character.

SPEAKER_03 1:45

He was um born in 1747.

SPEAKER_04 1:49

Oh, so just last week.

SPEAKER_03 1:50

And he was pretty much a self-made New England businessman.

SPEAKER_04 1:55

So we're in the Americas.

SPEAKER_03 1:57

Okay. But he's he's got some flair.

SPEAKER_04 1:59

Oh, like Rick Flair?

SPEAKER_03 2:01

Like he's pretty fucking lucky.

SPEAKER_04 2:02

Oh, okay.

SPEAKER_03 2:03

He's a lucky man.

SPEAKER_04 2:04

What made him lucky?

SPEAKER_03 2:06

I will tell you.

SPEAKER_04 2:07

Oh, do tell.

SPEAKER_03 2:08

So he was born just outside of Boston to poor Irish immigrant farmers. Sure. So he had very little formal education. Right. And he was working in the fields when he was little.

SPEAKER_04 2:21

Do you know what kind of crops they did?

SPEAKER_03 2:24

I'm gonna guess potatoes.

SPEAKER_04 2:26

That's what I was hoping you would say. Being Irish immigrants and all.

SPEAKER_03 2:30

I don't say potatoes.

SPEAKER_04 2:31

Potatoes. Poters, you mean put them in a stew? Sorry.

SPEAKER_03 2:36

What is it? Boyle measure.

SPEAKER_04 2:38

Put them in a stew or something, whatever, yeah. You know, potato potatoes. Uh I gotta love Samwise Gamge.

SPEAKER_03 2:45

Uh-huh. Um, so he was in the fields by age eight, and by 14, he was actually an apprentice for like a leather dresser.

SPEAKER_04 2:53

A leather dresser?

SPEAKER_03 2:54

Yeah, so he he knew how to make leather goods.

SPEAKER_04 2:57

Sure, sure. Wow, that's I mean, pretty good at 14. Yeah. I know times were different back then, and you had to learn a skill pretty early because you're about to die in three years, but that's impressive.

SPEAKER_03 3:08

And he had kind of a sharp eye for opportunity.

SPEAKER_04 3:11

Yeah.

SPEAKER_03 3:12

So around 1769, he moved to um New Berryport, Massachusetts.

SPEAKER_04 3:18

You I'm sorry, you said he was born in 47. Is that right?

SPEAKER_03 3:22

Yes.

SPEAKER_04 3:23

So he would have been about 22 at this point. Okay.

SPEAKER_03 3:25

And New Berryport, Massachusetts is quite a bit north of Boston. It's right on the border of I think it's New Hampshire.

SPEAKER_04 3:35

Oh man. Oh my god. Geography, am I right?

SPEAKER_03 3:38

I I don't do the New England area very well.

SPEAKER_04 3:42

It's all so combined because it was obviously the original colonies and everything. So it's I always get confused.

SPEAKER_03 3:47

And all the borders are so funky monkey.

SPEAKER_04 3:49

Oh, they were. More or less, yeah. I mean, look at look at North and South Dakota. Yeah. Or even the what is it?

SPEAKER_03 3:58

Kansas and Colorado.

SPEAKER_04 3:59

Arizona, New Mexico, Nevada, and um Colorado. The the four corners. It literally, it's like just a fucking squared off and everything. So yeah.

SPEAKER_03 4:09

Yeah.

SPEAKER_04 4:10

Things were a lot different back then. Yeah. So fair enough.

SPEAKER_03 4:14

So um this Newberryport, Massachusetts was a town that launched 70 ships alone that year.

SPEAKER_04 4:21

Ships for what? Like naval?

SPEAKER_03 4:23

Just poor uh trading. Oh, okay.

SPEAKER_04 4:26

Gotcha.

SPEAKER_03 4:27

So Dexter didn't exactly like climb the ladder to success. He actually rode an elevator. Like, fun fact, they didn't have elevators back then, but we're gonna say like he rode the elevator because that's how quickly he rose.

SPEAKER_04 4:42

So he skyrocketed.

SPEAKER_03 4:43

It's like skyrocketed.

SPEAKER_04 4:46

Wow. Jesus Christ. They didn't have elevators back then, but let's just say they did. That's what he would have been on. Okay. Climbing the corporate elevator.

SPEAKER_03 5:00

So he married Elizabeth Frothingham.

SPEAKER_04 5:04

Frothingham. Wow.

SPEAKER_03 5:06

She was nine years his senior. She had an endowment, and he married her and had got the money. I mean, he wasn't like a tool or anything. You just it is what it is.

SPEAKER_04 5:18

Inherited it through marriage. Yes. More or less.

SPEAKER_03 5:21

So he started trading in everything from moose high trousers and gloves to whale blubber and animal hides.

SPEAKER_04 5:27

What was the moose high trousers?

SPEAKER_03 5:30

Moose high trousers.

SPEAKER_04 5:31

Moose hide. I'm like, moose high. I'm like, what? Hide. Sorry. I that was a mishearing.

SPEAKER_03 5:38

That's okay. And then by the end of the Revolutionary War, he had tucked away a few thousand dollars and he did something most would consider financial suicide. Sure. He poured it all into continental currency.

SPEAKER_04 5:53

Continental currency.

SPEAKER_03 5:54

This was the first paper money issued by the Continental Congress from 1775 to 1779.

SPEAKER_01 6:02

Okay.

SPEAKER_03 6:03

And that was to finance the American Revolutionary War.

SPEAKER_01 6:06

Right.

SPEAKER_03 6:07

The notes were essentially bills of credit and were not backed by gold or silver.

SPEAKER_04 6:13

Right.

SPEAKER_03 6:14

But rather the anticipation that we would come out on top. Yes.

SPEAKER_04 6:19

That's quite the gamble.

SPEAKER_03 6:21

Yes. So the value of the currency plummeted due to an oversupply of notes. Well, yeah. It was printed by both the states and Congress.

SPEAKER_04 6:31

Oh, really?

SPEAKER_03 6:32

I didn't I didn't know that. And then it was also counterfeited a lot by British forces. Right. So by 1781, it took$100 in Continental to purchase just one dollar in hard currency.

SPEAKER_04 6:49

That sounds like a terrible return.

SPEAKER_03 6:51

Yes.

SPEAKER_04 6:52

But somehow eternal turn.

SPEAKER_03 6:55

Thanks to Alexander Hamilton's post-war financial reforms.

SPEAKER_04 7:00

Do they talk about this in the musical?

SPEAKER_03 7:03

I don't recall. I've never watched it. Yeah, I don't recall. But he created basically the first US bank. Ish Treasury or something? Yeah. So those near worthless bills were redeemed at full value. Wow. Turning Dexter overnight from a trader to a millionaire.

SPEAKER_04 7:26

And that's traitor with a D.

SPEAKER_03 7:29

Yes.

SPEAKER_04 7:30

Yes. Because, you know, tumultuous times and all.

SPEAKER_03 7:36

So now he's flush with cash, and Dexter bought a fleet of ships and res revived an overseas trading business. But he wanted, he had bigger dreams. He wanted status, not just the money. He wanted status.

SPEAKER_04 7:50

He wanted to be known.

SPEAKER_03 7:51

So he moved to Boston for a little bit. Um and he tried to lobby for like their elite for recognition, but was snubbed by by society. Yeah.

SPEAKER_04 8:00

Why why do you think that was?

SPEAKER_03 8:02

He was just kind of a kooky guy. He wasn't educated. Yeah.

SPEAKER_02 8:06

Yeah. Okay.

SPEAKER_03 8:07

Um, so he took his wealth and relocated back to Newberryport, and he was determined to carve out his own eccentricities.

SPEAKER_04 8:15

Okay.

SPEAKER_03 8:15

So let's talk about his dumb luck.

SPEAKER_04 8:19

Oh dear. Okay.

SPEAKER_03 8:20

Sure dumb luck.

SPEAKER_04 8:23

What's that from?

SPEAKER_03 8:24

Harry Potter. Um Professor McGonagall said something about pure dumb luck. Anyway.

SPEAKER_02 8:33

Yep.

Chasing Status And Snubs

SPEAKER_03 8:33

So once in New Berryport, Dexter's Wealth and Confidence spawned a series of Lucky as F business ventures.

SPEAKER_04 8:42

Okay.

SPEAKER_03 8:43

Experienced merchants secretly egged him on, hoping to destroy him.

SPEAKER_04 8:48

Why would you want to do that? I mean, seriously.

SPEAKER_03 8:50

He just wasn't.

SPEAKER_04 8:51

He was different.

SPEAKER_03 8:52

He was different, and people didn't like that. Well, you know what? They didn't go fuck right off. I don't think he was a tool or a rude man. He was just, I don't know. I think he was just different. Yeah. Um, so a neighbor advised Dexter to ship brass bedwarmers.

SPEAKER_04 9:11

Bed warmers. Like what in Pirates of the Caribbean? Yes. Nice.

SPEAKER_03 9:15

They put coal and stuff in there and they shove it under the yeah.

SPEAKER_04 9:18

I still can't believe they fucking did that. I know. How many people died because of that?

SPEAKER_03 9:22

Yeah, I don't know.

SPEAKER_04 9:23

Seriously. You can't tell me that some of the embers wouldn't lit those fucking linens that they used to have.

SPEAKER_03 9:28

Full of down feathers.

SPEAKER_04 9:30

And whatever. Whatever. Yeah. Hey? I don't know.

SPEAKER_03 9:33

Oh, we don't know. We weren't there.

SPEAKER_04 9:35

I wasn't there. So I don't even think that really happened.

SPEAKER_03 9:38

This neighbor said ship brass bedwarmers to the Caribbean.

SPEAKER_04 9:44

Which is literally what we just fucking said. Jesus Christ.

SPEAKER_03 9:47

But like the Caribbean is the tropics.

SPEAKER_04 9:50

Yeah.

SPEAKER_03 9:50

The Caribbean, they probably aren't going to use it very often as bedwarmers. Except for Empires of the Caribbean.

SPEAKER_04 9:59

But Elizabeth Swan used them.

SPEAKER_03 10:01

Dexter purchased, give or take,$42,000.

SPEAKER_04 10:06

Oh my did you come across at all what like one of those cost by chance?

Bedwarmers Become Molasses Tools

SPEAKER_03 10:12

No, but I have a picture of it if you want to see what it looks like.

SPEAKER_04 10:15

Oh, that show tells me the price.

SPEAKER_03 10:17

I know. That's what I thought.

SPEAKER_04 10:18

I mean, I've seen them. You don't. Oh. There's a nice glare. Yep, there it is. Look at that. Looks like a what's the sea creature with the right?

SPEAKER_00 10:29

Yeah.

SPEAKER_04 10:30

What the fuck's the name of that? I don't know. But you know what I'm talking about, right?

SPEAKER_03 10:33

I do.

SPEAKER_04 10:33

Oh my god, I'm drawing a blank on the name.

SPEAKER_03 10:36

Anyways.

SPEAKER_04 10:37

Almost like a uh seashell crab?

SPEAKER_03 10:41

Sure.

SPEAKER_04 10:42

Is that what it is?

SPEAKER_03 10:43

Sand dollar?

unknown 10:44

No.

SPEAKER_04 10:45

You know what a fucking sand dollar is that? It doesn't have a tail.

SPEAKER_03 10:48

Doesn't it? No. Okay.

SPEAKER_04 10:50

Anywho.

SPEAKER_03 10:51

Anyway, so we're talking about the tropics here.

SPEAKER_04 10:53

We sure are.

SPEAKER_03 10:54

42,000 bedpans. Warming pans.

SPEAKER_04 10:57

Bedpans.

SPEAKER_03 11:01

If you need a shit, I got you. Upon arrival, plantation owners rebranded them as molasses strainers and ladles. Because it's holy.

SPEAKER_04 11:16

Well, yeah, I mean, that makes sense.

SPEAKER_03 11:19

So they planted in sugar vets, the pans proved invaluable to molass the molasses industry. So Dexer sold them at 79% markup.

SPEAKER_04 11:32

Holy fuck. Yo. Jesus.

SPEAKER_03 11:35

They're like, screw you, neighbor. That's quite a they're like, yeah, I all said bedpans to the why do we keep saying bed pants?

SPEAKER_04 11:44

I don't know, but it's kind of funny.

SPEAKER_03 11:45

Oh my gosh.

SPEAKER_04 11:46

Bed warmers, everybody bedrooms.

SPEAKER_03 11:48

Oh my goodness. Okay.

SPEAKER_04 11:50

Wow, I do declare.

SPEAKER_03 11:53

Okay. Other traders tricked him into buying anthracite coal. Do you remember anthrocyte?

Coal To Newcastle During A Strike

SPEAKER_04 12:01

I was just gonna say we talked about this in umia, Pennsylvania.

SPEAKER_03 12:06

So just to kind of refresh your memory, I took this directly from our podcast episode. Anthracite is a hard black coal. Yep. It's a natural mineral with high carbon and energy content that gives off light and heat produce energy when burned, making it useful as fuel. It's 98% carbon and 2% away from being a diamond.

SPEAKER_04 12:30

Which is wild.

SPEAKER_03 12:30

Yeah. Anthracite coal was primarily used for domestic heating and industrial purposes. Right. So traders tricked him into buying all this anthracite coal and sending it to Newcastle, England's coal capital. A city famous for its mines.

SPEAKER_04 12:52

There's a really there you okay, let me rephrase that. There used to be a really good beer called Newcastle. Imported from, obviously, to England. Newcastle. And then um kind of was going down, going down, and then Laganitas kind of bought them, and it's brewed here, and it's more of a craft beer. It's not the same. It's unfortunate. It's still okay, but I don't know. Anyways.

SPEAKER_03 13:19

So sending coal to a coal mining city.

SPEAKER_04 13:23

Right. Yeah, yeah.

SPEAKER_03 13:24

Miraculously, oh dear, the local miners were on strike.

SPEAKER_04 13:30

Come on.

SPEAKER_03 13:32

Dexter unloaded his cargo at a premium price during the sort shortage, again making bank.

Exporting Cats For Pest Control

SPEAKER_04 13:39

What what are the fucking chances?

SPEAKER_03 13:43

Oh, but we ain't done yet.

SPEAKER_04 13:45

I know. Jesus. I mean, seriously, of all the dumb fucking luck, he's got fucking strikes and molasses strainers. Jesus Christ.

SPEAKER_03 13:55

So Dexter noticed that in New Berryport there was a surplus of stray cats.

SPEAKER_04 14:01

Like the band?

SPEAKER_03 14:03

No.

SPEAKER_04 14:03

Like extra records? Cat cats. I got it. The stray cats are a band.

SPEAKER_03 14:08

Stray cats. Okay.

SPEAKER_04 14:09

Yeah. Anyways.

SPEAKER_03 14:10

He collected dozens of cats and shipped them to the Caribbean Islands where plantation houses needed. Yep. Mm-hmm. Yep. And of course, the plan worked perfectly. Of course it did. Grateful Islanders bought the cats to act as pest control, and Dexter turned it into a profit.

SPEAKER_04 14:30

That's fucking wild. I mean, it makes sense though. But also, like, it's funny when people did that, especially back in the day. Like they didn't know better. Cats can be invasive depending on their environment. And almost could be bad. Like bunnies in Australia. I think is I think that's one of the places, right? Or is it bunnies in Australia? I don't remember. There's something that they introduced into Australia, and now it's like not good. Oh really?

SPEAKER_03 15:00

Oh wow.

SPEAKER_04 15:01

Or even like um recently, not that long ago, they released these wolves that were causing mischief up in the I think it was the Pacific Northwest. They moved them to fucking Colorado. Do you know where they put them? Near fucking farms? Oh. I wonder what they're gonna eat. I don't know. Cows.

SPEAKER_03 15:21

Why do they do that?

Whale Bones And The Corset Boom

SPEAKER_04 15:22

Because they're idiots. But um, yeah, it's like good on him for getting the mice and the rats or whatever, but or rats, you said, but um cats and yeah, cats and rats. Cats and rats living together. It's mass hysteria.

SPEAKER_03 15:35

Okay, so again, okay, Dexter was hoarding a large quantity of whale bones, bay we baleen whales.

SPEAKER_04 15:45

Yeah.

SPEAKER_03 15:45

Um, apparently by mistake, like, what am I gonna do with all these bones? I'll just keep saving them, you know, kind of a thing.

SPEAKER_04 15:51

So that's when he because from he was getting the whale blubber before, which is what made it that was made mainly for oil lamps. Oil lamps, yeah. Yeah.

SPEAKER_03 15:59

So baleen whales were used in the 1700s for various products, but could be oversupplied.

SPEAKER_02 16:06

Sure.

SPEAKER_03 16:06

So Dexter was had what was said to have cornered the market, amassing hundreds of tons of whale bones. And this caused people to call him just, you're a freaking idiot, dude. What are you doing with all these? It's like I'm waiting for the right time, fuckers. The right time has come because fashion has come to the rescue. Baleen whale bones became highly sought for ladies' corset stays.

SPEAKER_04 16:33

Yep. I I kind of thought that's where you were going. What the fuck? I mean, and corsets were very info popular, whatever you whatever terminology you want to use in that time frame. That's wild.

SPEAKER_03 16:48

He sold his Elizabeth Swan. Elizabeth Swan.

SPEAKER_04 16:52

It's the newest fashion. Bailey whale bones.

SPEAKER_03 16:55

Dexter sold his horde at 75% markup.

SPEAKER_04 17:00

Oh my god. Wow. So who would you sell that to?

SPEAKER_03 17:04

Just like um fashion seamstresses, probably.

SPEAKER_04 17:09

Or whatever companies make. Yeah, and the seamstresses but blah blah blah. Okay. That's wild.

SPEAKER_03 17:15

And I want to say his wife Elizabeth sold notions, which are things that go with sewing, like little doodads. Oh, needles and thread and gotcha. Thimbles and what what did you call them?

SPEAKER_04 17:28

They're called notions. Oh, I've never heard that before. Yeah. Interesting.

SPEAKER_03 17:31

Okay.

SPEAKER_04 17:32

Okay.

SPEAKER_03 17:32

So what next? Each impossible success, his reputation grew. Of course. Um, biographers later argued that Dexter may have understood basic market forces, but better than what people gave him credit for.

SPEAKER_04 17:48

Yeah, they just thought it was complete dumb luck. Yes. But maybe there was something to it.

Mansions Statues And Self-Myth

SPEAKER_03 17:53

It's possible that he inquired where goods were scarce and cornered that market. Sure. Um, but in any case, by 1792, Dexter's fortune was immense. Yeah, he owned large ships and a yacht, and he um launched trade voyages to the West Indies and to Europe. Wow. By the 1790s, Dexter was a millionaire, but he still craved attention and status.

SPEAKER_04 18:16

He wanted everything.

SPEAKER_03 18:18

Yes. So he purchased a grand brick mansion on High Street in Boston or Newberryport. I actually didn't look up where it was. But it's still there, it still exists. Oh, okay. Is it a museum now? Uh no, I don't I I didn't look into it, but it's still really pretty. Yeah. But um he put a gilted eagle atop its roof. A gilded gild gilt? A gilded gilded eagle atop its roof.

SPEAKER_04 18:47

Not a gilded.

SPEAKER_03 18:49

And Turkish style towers capped with golden balls.

SPEAKER_04 18:54

So it kind of looks like Aladdin's castle.

SPEAKER_03 18:56

Aladdin?

SPEAKER_04 18:57

Well, the the not his castle, but right? The bulb bulbous tops and towers? Is that what you're saying?

SPEAKER_03 19:07

No, I don't I don't think so. No, it's more colonial looking.

SPEAKER_04 19:11

You know what's really funny? There was an old uh video arcade place in the 90s we go to called Aladdin's Castle. I just remember that. My brother Ryan had his birthday party there once.

SPEAKER_03 19:23

Nice. Yeah. In front of his house, he built outdoor museum statues. So 15-foot tall columns with figures of world history on top. He had George Washington on one, he had John Adams on one, Thomas Jefferson stood on one, um, Napoleon, Adam and Eve, a pair of lions.

SPEAKER_04 19:50

Like wait, Napoleon?

SPEAKER_03 19:52

Mm-hmm.

SPEAKER_04 19:53

Was he like relevant at this time?

SPEAKER_03 19:56

I I guess so.

SPEAKER_04 19:59

Guess so. You were well, yeah, I know he was like the early 1800s. What year are we talking?

SPEAKER_03 20:03

Um, we're talking late 1700s.

SPEAKER_04 20:06

I don't think Napoleon was okay. Fact check that.

The Fake Funeral And Backlash

SPEAKER_03 20:11

So Dexter was a millionaire in the 1790s, and Napoleon was born in 69, 1769.

SPEAKER_04 20:20

Oh, all right. I just always think of Napoleon in like the early 1800s, I guess. Because that's when he's most notable.

SPEAKER_03 20:28

Yeah.

SPEAKER_04 20:29

Anyways.

SPEAKER_03 20:30

Anyways. Um, two of the statues were of Dexter himself. That's not vain at all. One proudly barred the inscription, quote, I am the first in the east, the first in the west, and the greatest philosopher in the Western world.

SPEAKER_04 20:48

What a douche. Pokey dokie. Yeah, that's more than quirk. That's super douche.

SPEAKER_03 20:53

So Dexter went as far as to anoint himself Lord Timothy.

SPEAKER_04 20:59

Oh my god.

SPEAKER_03 21:00

He painted his coat with a coat of arms and took to wearing um glittering regalia. In social situations, he insisted friends and servants address him as Lord Dexter. And he even floated plans to become Earl of Chester in New Hampshire, offering land or a feast to anyone who would agree to do it. Jesus Christ. Graceful merchant found um Dexter's castle house, whatever, kind of gaudy.

SPEAKER_01 21:43

Yeah.

SPEAKER_03 21:43

Um he wasn't an aristocrat by birth or manners, and the nobles mocked his um badges of rank, rank. Um, and despite the uproar, Dexter's outlandish style did not deter him. He was like, That's fine. I'm still lucky.

A Pickle For The Knowing Ones

SPEAKER_04 21:59

Look at me though. I don't need y'all. Look at my what I got.

SPEAKER_03 22:03

This becomes a little toolish. Um, he staged his own funeral in 1806 to see who would mourn his death.

SPEAKER_04 22:13

So, like he pretended to die? Yeah. Okay, he's now a douchebag.

SPEAKER_03 22:18

Yeah. Several thousand townspeople showed up for the procession, and afterwards, Dexter did pop out of hiding saying gotcha, but then angrily struck his wife for not crying enough during the service.

SPEAKER_04 22:35

Were it please tell me he popped out of the fucking coffin?

unknown 22:38

I don't know.

SPEAKER_04 22:39

Because if he didn't, then he fucking failed. Because if you're gonna be a douchebag and stage your own and then hit your wife for not crying enough at his fake funeral funeral, maybe she knew it was fake.

SPEAKER_03 22:54

Well, she wasn't crying.

SPEAKER_04 22:56

That's what I was just gonna ask. It's like, okay, if she was in on this, she's clearly not a good actress, but that's also not her profession. So maybe not be a tool bag.

unknown 23:10

Wow.

SPEAKER_03 23:10

So by his own account, Dexter was something of a philosopher as well.

SPEAKER_04 23:14

He wasn't, but okay.

SPEAKER_03 23:15

In 1802, he published a little 24-page volume titled A Pickle for the Knowing Ones. This pamphlet contains zero punctuation.

SPEAKER_04 23:29

Oh, good lord.

SPEAKER_03 23:30

There is an occasional capital letter, um, but there was eccentric spelling, run-on sentences, obviously, because there's no periods. Dexter used it to boast of his deeds and attack critics, including mocking his wife and town officials.

SPEAKER_04 23:46

Well, what did he have against his wife? Seriously, what the hell?

Luck Versus Judgment

SPEAKER_03 23:51

Readers who um grived about the lack of commas were giving a solution. Dexter quietly printed a separate page of dots and dashes telling readers that they could salt and pepper the text wherever they pleased.

SPEAKER_04 24:07

I'm really starting not to like this guy.

SPEAKER_03 24:10

Dexter gave away copies for free, um, and the public still snapped them up.

SPEAKER_04 24:15

Because who would buy that?

SPEAKER_03 24:17

But it went through at least eight printings in the early 1800s.

SPEAKER_04 24:21

That's impressive.

SPEAKER_03 24:22

And long after Dexter's death, the book remained a bizarre collectible, obviously, because it is kind of odd.

SPEAKER_04 24:27

Well, yeah, and like I'm sure it stopped printing at some point.

SPEAKER_03 24:32

So to his contemporaries, Dexter was a mix of spectacle and astonishment. Newspapers labeled him as a ridiculous millionaire of Newberry Port. In 1806, obituary bluntly called him, quote, one of the most eccentric men of his time, and noted that his intellectual endowments were not of the most exalted step.

SPEAKER_01 24:54

All right.

SPEAKER_03 24:55

Wealthy neighbors assumed he was a fool. It was hard to believe any man so uneducated could succeed the way he did.

SPEAKER_04 25:02

Yeah, just pure dumb luck at their thinking.

SPEAKER_03 25:06

So while after a century a half a century after Dexter's death, one chronicler wrote that everything he undertook worked well, not by luck, as many thought and said, but by most excellent judgment.

SPEAKER_04 25:21

Which is possible.

SPEAKER_03 25:22

So Dexter may not have been a total fool, rather, he was just a total tool. Immensely lucky, yeah, that's true, but also willing to gamble where others wouldn't.

Wrap-Up And Listener CTA

SPEAKER_04 25:32

Well, and that's sometimes what you need to do because there are a lot of people who be like, I got this great idea, and they won't go through with it because they just can't risk the gamble per se. Whereas he's like, I'll do it. Yeah, I'll I'll send uh as you would call it bedpans to the Caribbean, um, bedwarmers to the Caribbean. He's like, Yeah, sure, why not? Yeah, how many you got? I'll buy them all. I'll buy the lot I'll take the lot.

SPEAKER_03 25:57

Take the lot.

SPEAKER_04 25:58

Yeah, Harry.

SPEAKER_03 25:59

So that was Timothy Dexter, one of the luckiest bastards in the 1700s.

SPEAKER_04 26:07

That was weird. Yeah, it got weird at the end. Not even his luck was weird, he got weird.

SPEAKER_03 26:13

He got weird.

SPEAKER_04 26:14

Because what the fuck? Do you think any of his statues still remain?

SPEAKER_03 26:19

I don't know. But his house is still there. That's what you said. So I wonder it's pretty.

SPEAKER_04 26:23

I I bet. I wonder if any of the statues are still at the house or if they've been removed and/or whatever.

SPEAKER_03 26:29

I'm gonna guess one of them is at House on the Hill. Or is it House on the Rock?

SPEAKER_04 26:33

House on the Rock. House on the Rock. Really? You think one would be there?

SPEAKER_03 26:36

Oh.

SPEAKER_04 26:37

The guy who who made House on the Rock, he would totally get that. Yeah, I mean, you're not wrong. We should look into that and see if something like that is the case, because um, maybe we should do a buffoon's trip to the House on the Rock. I haven't been there in a long time.

SPEAKER_03 26:51

I went there a couple years ago with Nathan. And it was the what they say, like allow four hours to get through it, but like by hour two and a half, three, I'm like, let's just get through it. Yeah, can I just so like everything at the end, like I hardly even looked at because it was just too long.

SPEAKER_04 27:08

Maybe if we go there, we speed through the front, then you slow it down.

SPEAKER_03 27:13

There you go.

SPEAKER_04 27:14

I mean, right?

SPEAKER_03 27:15

I mean, you're not wrong. We could do that.

SPEAKER_04 27:17

I couldn't tell you the last time I've been there. It's been a it's been probably twenty.

SPEAKER_03 27:23

It's cool if you've never been very eclec um very eclectic. Eclectic.

SPEAKER_04 27:28

Yep. Or electric or whatever you're gonna say. Hoarding is a understatement.

SPEAKER_03 27:34

Yeah, big hoarder. Excuse me, but big hoarder of weird things.

SPEAKER_04 27:38

Oh just weird, eccentric shit.

SPEAKER_03 27:40

Like this guy has a whole huge carousel in his house, which is wild. Yeah, he's got a whole whale in his house.

SPEAKER_04 27:50

Do you remember? Um, I think I'm pretty positive I showed you this, so if I didn't, I apologize. But do you remember my old bank that I have with the whale? And it's like the you put the coin on the guy, it's Jonah and the whale.

SPEAKER_03 28:02

Yeah, I had a panda one.

SPEAKER_04 28:04

Yeah. Um that is it, the house of the rod.

SPEAKER_03 28:07

Oh, okay.

SPEAKER_04 28:07

But I think his is real. Mine's uh knockoff. Import knockoff or whatever. But I've also had it for probably 40 years, so fuck off.

unknown 28:15

It's good.

SPEAKER_04 28:17

Means something to me. It's from I think I got it from my godfather, actually. But anyways. Well, I suppose. All right, buffoons. That's it for today's episode.

SPEAKER_03 28:28

Buckle up because we've got another historical adventure waiting for you next time. Feeling hungry for more buffoonery? Or maybe you have a burning question or a wild historical theory for us to explore?

SPEAKER_04 28:39

Hit us up on social media. We're History Buffoons Podcast on YouTube, X, Instagram, and Facebook. You can also email us at history buffoonspodcast at gmail.com. We are Bradley and Kate, music by Corey Akers.

SPEAKER_03 28:53

Follow us wherever you get your podcasts and turn those notifications on to stay in the loop.

SPEAKER_04 28:58

Until next time, stay curious and don't forget to rate and review us.

SPEAKER_03 29:02

Remember, the buffoonery never stops.