Historical Lord Timothy Dexter - America's First Lolcow who constantly failed up and felted his alogs. The original teflon tard.

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Lolcows Of History

Lord Timothy Dexter

There is no reason to believe this is what he looked like.
All art is fake AI slop unless otherwise noted and is only here to break up what would otherwise be a wall of text.
Born in Malden, Massachusetts in 1747, Timothy Dexter was a leatherworking apprentice who gained wealth, status, and luxury entirely through poorly considered hair-brained schemes that were wildly successful thanks to inhuman amounts of sheer retard luck.

I Was Born When Grat Powers Rouled

Dexter came from a poor family of Irish immigrants and dropped out of school at the age of 8 to work on a farm and, later, as a leatherworking apprentice.

But Dexter had a dream - get rich or die trying. But having intelligence below average even for someone with only a second grade education he was going to need a jumpstart. This is where the wealthy and recently widowed Elizabeth Frothingham, 10 years his senior at 32-years-old, came in. They were wedded and moved to a newly acquired mansion in Newburyport, MA.

Mr. and Mrs. Dexter sold goods out of their home to make a living with Timothy selling leather goods thanks to his previous experience in the field and Elizabeth selling sewing accessories.

Leatherworking Apprentice Days
But this wasn't enough for Timothy Dexter. With this new financial foundation Dexter was ready to embark on business ventures that would be unheard of outside of a Polack joke.

Very Lucky in Spekkelation

Haters gonna hate

Elizabeth had some good money, but for the kind of dreams Dexter was dreaming he needed more and that requires investments. In the post-Revolutionary War equivalent of betting it all on HawkTuah Coin Dexter bought up scads of the now-worthless Continental Currency, a currency that had become literally synonymous with having no value as the phrase "not worth a Continental" grew in popularity. Soon after he bought these up the Massachusetts and Federal governments announced they would make good and pay out to anybody holding Continental Currency and Dexter's bank account went to the moon in the first, but not the last, run of ridiculous, undeserved luck he would experience.


Thay All Lafed
nobody liked him
Now, riding high on his success, the real fuckery could begin but, first, Dexter needed to get in good with New England high society and command the respect he so richly deserves. Upon trying to integrate into their society Dexter was immediately seen as the local nouveau riche retard - the colonial equivalent of making your living off of your hustle culture youtube channel and then moving to Greenwich, Connecticut and expecting to be the big man on the scene. Being an unrefined, uncultured, rock stupid braggart, Dexter was openly mocked by his desired peers.

He wasn't going to let this small setback stop him, though. Dexter was granted the title of Lord Timothy Dexter by a source he recognized and deeply respected. Timothy Dexter.

Dexter figured if he wanted to earn respect, then he must hold a public office. His grand plan to get appointed to a public office was simple - keep bugging the local government until they give in. So Dexter wrote letter after letter to them demanding a public office. Eventually they got so tired of this retard endlessly writing letters that they acquiesced and gave him the official title of "Informer of Deer". Dexter's job was to keep a running count of all the deer in the town. Though the officials had knowledge that Dexter didn't: Newburyport doesn't have any deer.

Grat Day of Regoising

Cat trading
Sated with his new public office, ships that he had commissioned with his currency speculation fortune were ready to go, but what would his new business venture be? It was research time and Dexter was ready to pick some brains. He reached out to his perceived peers for advice and was told he should try to sell bed warmers to the West Indies. Dexter thought this was a wonderful idea and took him up on it. Unfortunately for Dexter he didn't realize that this was the business advice equivalent of just saying "Blow me, faggot." as the West Indies have no need for bed warmers what with it already being hot as living shit.

Bed Warmer
A real picture of a Colonial Bed Warmer
Upon arrival in the West Indies with a boatload of bed warmers, the locals were ecstatic. They desperately needed ladles for the local molasses industry and these would do nicely. Dexter sold his bed warmers ladles for a tidy sum and headed back to Newburyport.

With the friendly local advice working so well for him he again asked his "friends" what he can import to the West Indies. Upset he wasn't bankrupted they decided to try their luck again. "Wool mittens." they suggested.

And so he did. He loaded up his boat with wool mittens and headed to the West Indies. Unfortunately, there was no way this would work out as locals did not need wool mittens since, of course, it's very hot there. However, Asian traders that they happened to meet en route to the West Indies were on their way to Siberia and the mittens would do them a world of good. He unloaded them before he even got to his destination.

Dexter once again, in a bout of phenomenal luck, headed back to Newburyport an even richer man.

It almost seemed like a local game now to try to successfully bankrupt the village retard by sending him on fools errands. Now they suggested he sell coal to Newcastle. That one seems pretty reasonable until you realize that Newcastle was a town known for being a coal stronghold for the entirety of Europe. They presumably already had so much coal any new coal would be damn near worthless to them and probably came from Newcastle in the first place.

Dexter Always Wins
So, of course, Dexter went there with a boatload of coal and, as if The Lord himself was having a bit of fun, the Newcastle miners were on strike and the coal that the local economy was built upon was, for probably the first time in Newcastle's history, selling at a premium. Dexter sailed back to Newburyport with yet another hefty profit.

He even exported bibles to the godless West Indies, a venture sure to fail, that is if Christian missionaries didn't arrive there a month prior who bought all the bibles up.

Newburyport had a cat infestation they wanted to get rid of and the voice in Dexter's head screamed "It's free real estate!" prompting Dexter to load up his boats with cats and bring them to the Caribbean to see if they wanted them. Want to guess who was having a rat infestation at that time? Yeah. He sold them.

He also purchased a lot of whale bones for some reason. In fact, he purchased all the whale bones. At this point there's two schools of thought on what he did with it. One, sourced from Dexter himself, is that he sold them all for ship stain. Nearly every historian, however, said he sold them to the growing corset market. Either way, he sold them all and at a big markup.

The man was clearly blessed to succeed at anything he did, the stupider the better, with his entire professional life working out like playing Anno 1701 in god mode with mods. His erratic actions and improbable fortune led people to wonder if he was truly a dipshit, or just acting like a dipshit to keep people from following in his footsteps and muscling in on his business.

His personal life demonstrates that he is, indeed, just a lucky dipshit.

Ime The First Lord In The Younited States of A Mercary

His staged funeral
Despite his success Dexter was still a loud, self-aggrandizing asshole and nobody liked him. This damaged his fragile ego and he would try to repair it in any way he could. One way was to stage a funeral for himself. He figured that seeing everybody mourning the loss of the great Lord Timothy Dexter would help assuage his damaged ego. The charade didn't last long though as Dexter, watching from hiding, saw his wife wasn't mourning well enough since she was laughing and chatting with guests, so he blew his cover by beating the shit out of her with a cane and berating her in front of everybody.

Timothy's hatred of his wife was widely known around Newburyport, with him eventually telling people she died and, when dealing with someone who actually saw his wife, simply referring to her as a ghost that haunted his home.

Timothy chased clout from the refined elite whenever he could, even gathering locals to his home for a speech Dexter decided to give in the most pinkies up language he could think of, French.

Timothy Dexter did not speak French.

Humble
In an attempt to jerk himself off and be what he saw as a very fancy boy, indeed, he commissioned a statuary garden with 40 statues of great men including George Washington, Napoleon, Thomas Jefferson and, most importantly Timothy Dexter. His statue of himself bore the inscription "I am the first in the East, the first in the West, and the greatest philosopher in the Western world." If this wasn't masturbatory enough, all the statues were displayed on 15 foot high columns.

800px-A_view_of_the_mansion_of_the_late_Lord_Timothy_Dexter_in_High_Street_Newburyport_1810_by...jpg
A real painting of his mansion with the statues.

He hired a painter to paint the statues and the inscriptions on the plinths when he noticed that the painter was writing on Thomas Jefferson's statue that Jefferson was the author of the Declaration of Independence (he was). Dexter was infuriated with the painter and corrected him, telling him that Jefferson actually the writer of the US Constitution (he was not). The painter stood up for himself, telling Dexter that he was mistaken, that Jefferson wrote the Declaration not the Constitution. Timothy marched himself into his mansion, sat himself down in his library, and found that, indeed, Jefferson wrote the Declara-- no just kidding, Dexter didn't do any research, he just came out with a gun, shot it into the air and made the painter change the inscription on threat of his life.

With acceptance among the elites seeming to be a lost cause he considered that if he couldn't command respect maybe he could pay for it. Dexter purchased an estate in Chester, New Hampshire. When there he asked people to call him the Earl of Chester. Children that did this were paid a quarter. Adults that did this were given dinner and drinks.

Dexter also offered to pay off town officials of Chester to change the name of Chester Street, the street his estate was on, to Dexter Street, offering to pay for this favor by paving the streets in granite cobblestones. The officials cordially invited him to fuck himself.

Being rich, Timothy started to amass a following of sycophantic yes men but, unlike respectable rich people of the time, his followers tended to be more of a Colonial era Wack Pack. This included:

Jonathan Plummer - Dexter's bard poet. A man who was kept around to write poetry about Timothy Dexter, despite not being very good at poetry and was, by trade, a fish monger and pornography merchant.

John P. - A schoolmaster-cum-charlatan, John P started life as a schoolteacher with a penchant for tests of courage. He found it was hard to keep that job when his tests of courage included locking pupils up in a charnel house among the corpses of dead priests. He later became a fraudulent astronomer who was convinced he would never die unless "the sun was blotted out of the heavens." He died on June 16, 1806. It was a total solar eclipse.

Dwarf Billy - The deliciously ironically named "Dwarf Billy" was actually Dexter's powerful 6' 7" brute. Threatened to skin and eat a sea captain who badmouthed Dexter. Eventually Dexter's retardation proved too much for Dwarf Billy and he exited Dexter's entourage.

Voise of the Peopel

After making a sizable fortune off of the dumbest business ventures the world had ever seen, Timothy Dexter decided to put yet another feather in his cap and become a writer.

Staged, since he probably couldn't read.
At age 50 A Pickle For The Knowing Ones, Dexter's book, was self-published. With Dexter being nearly illiterate and half a retard it was destined to be a flop with the content being nothing more than bragging about his money, rambling about the government, and declaring how much he fucking hated his wife. But, in one final burst of that Dexter tard magic, his book became 1802's version of The Room, with people buying it in droves to marvel at the poor spelling (each subheading of this OP are direct quotes from his book), the rambling, pointless nature of the writing, and the complete lack of punctuation anywhere.

In fact the book did so well that it warranted a second edition in which Dexter promised to include punctuation. Dexter delivered on his promise and encouraged his readers to "solt and peper" these in wherever they like:

Solid trolling tbh

The actual final page.
A Pickle For The Knowing Ones is available to read in full here.

I Cant See To Rite Aany More Fare Well I Say Good Bye

In 1806, Timothy Dexter died, leaving behind an estate worth $35,027.39 which is worth about $825,452.03 today.

Timothy Dexter shares so many parallels with modern lolcows - Chris Chan's delusions of grandeur, DSP's cosmic protection from consequences, Boogie's need for acceptance, Lowtax's love for beating his wife, the man was certainly a lolcow role model.

Are the stories about him exaggerated? Probably, but his actions, his achievements, and his legend will forever cement him as a true Lolcow Lord.
The follering peases are not my Riting but very drole

Ye Olde Doxe
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btw just to show off the translation process:

Before chatgpt:
To mankind at Large the time is Com at Last the grat day of Regoising what is that why I will tell you thous three kings is Rased Rased you meane should know Rased on the first Royal Arch in the world olmost Not quite but very hiw up upon so thay are good mark to be scene so the womans Lik to see the frount and all people Loves to see them as the quakers will Com and peape slyly and feele glad and say houe the doue frind father Jorge washeton is in the senter king Addoms is at the Rite hand the present king at the Left hand father gorge with his hat on the other hats of the middel king with his sword king Addoms with his Cane in a grand poster Adtetoude turning his fass towards the first king as if they was on sum politicks king our present king he is stands hearing being younger and very deafe in short being one grat felosfer Looks well East & west and North & south deafe & very deafe the god of Natur has dun very much for our present king and all our former ones they are all good I want them to Live for Ever and I beleave thay will it is hard work to be A king—I say it is hardar than tilling the ground I know it is for I find it is hard work to be A Lord I dont desier the sound but to pleas the peopel at Large Let it gou to brak the way it dus for Asort ment to help a good Lafe to Cour the sick spleney goutey dul frames Lik my selfe with the goute and so on make merry a Chealy Christen is for me only be onnest No matter what they worshep son moune or stars or there wife or miss if onnest Live forever [8]money wont gitt thous figers so fast as I wish I have sent to Leg horn for many mr bourr is one Amonks others I sent in the grand Crecham thous 3 kings Are plane white colow at present the Royal Arch & figers cost 39 pound wate silver the hiest Councaton order in the world so it is sade by the knowing one I have only 4 Lions & 1 Lam up the spred Eagel has bin up 3 years upon the Coupelay I have 13 billors front in strat Row for 13 states when we begun 3 in the Rear 15 foot hie 4 more on the grass see 2 the same hath at the Rite of the grand Arch 2 at the left wing 15 foot hie the Arch 17 foot hie the my hous is 3 sorey upwards of 290 feet round the hous Nater has formed the ground Eaquel to what you would wish for the Art by man Eaquel to a Solomun the onerabel Jonathan Jackson one of the first in this Country for tast borne A grat man by Nater then the best Lurning what sot me fored for my plan having so gran spot the hool of the world Cant Excead this to thous that dont know would think I was Like halfe the world A Lier I have traveled good deale but old steady men sayeth it is the first that it is the first best in this Contry & others Contrey I tell you this the trouth that None of you grat men wodent be A frunted at my preseadens & I spare Now Cost in the work I have the tempel of Reason in my garding 3 years past with a toume under it on the Eage of the grass see it cost 98 gineys besides the Coffen panted whit in side and out side tuched with green Nobel trimings uncommon Lock so I can tak the kee in side and haye fier works in the toume pipes and tobacker & A speaking trumpet and & bibel to Read & sum good songs What is a presedent answer A king bonne partey the grate has as much power as A king and ort to have & it is a massey he has for the good of mankind he has as much power as Any king for grat ways back there must be A head sum whare or the peopel is Lost Lik wild gees when thay Lous the gander two Leged want A head if fore Leged both & 2 Leged fouls the Name of presedent is to pleas the peopel at Large the sound souts best Now in the south give way to the North the North give way to the south or by & by you will brake what falers be wise on keep the Links to gether and if you cant A gree Consoalated to A kingly power for you must keep together at the wost hear it Labers ye les see there is so many men wants be the all offesers & Now sogers poor king Every day wants A bone sum more then others the king cant Live without the feald wee have had our turne grat good father Addoms [9]turne & turne About Rest Easey you all will be pleased with the present king give time all did I say Now but the magor part fore fifths at least.

After chatgpt:
To all of mankind, the time has finally come for great rejoicing! Why, you ask? I shall tell you. Three kings have been raised—raised upon the first Royal Arch in the world. Well, almost the first, but it is very high up and can be seen from afar. People, especially women, love to gaze upon it. Even Quakers come to take a sly look and feel pleased, saying, "How wonderful, friend!"
In the center stands Father George Washington, wearing his hat. To his right is King Adams, holding a cane in a grand and dignified pose, turning toward Washington as if discussing politics. To the left is our present king, younger and rather deaf. He stands listening, looking east, west, north, and south—truly a great philosopher. The God of Nature has done much for him and for all our past kings. They are all good, and I hope they live forever, for it is hard work to be a king. I know this, as I find it difficult even to be a lord. Yet, to please the people, I accept the title and labor on.
Now, let me tell you about the Royal Arch and its figures. I sent for these from Leghorn. They are plain white for now, but they will soon adorn the arch. The figures and arch cost 39 pounds of silver, as befits the highest consecration order in the world—or so the experts say. I also have four lions and one lamb displayed. The spread eagle has been atop the cupola for three years. My house is a marvel—three stories high, 290 feet around, with 13 pillars in the front to represent the original 13 states, and more pillars placed strategically around the grounds. The arch itself is 17 feet high, standing in grandeur.
Nature blessed this land, and art has completed it. Even the wisest travelers agree that this estate is unmatched. Some may doubt my words, but they are the truth, and no honorable man would be offended by my boldness.
The Temple of Reason stands in my garden, completed three years ago, with a tomb beneath it. The temple cost 98 guineas, and the coffin within is painted white, accented with green, and fitted with noble trimmings. The lock is so unique that I keep the key myself. I even have fireworks, pipes, tobacco, a speaking trumpet, a Bible, and songs stored there—ready for good company and reflection.
Now, what is a president? A president, like Bonaparte the Great, holds as much power as a king and rightly should for the good of mankind. History has shown that people need a leader, like geese need a gander, or chaos ensues. The title "president" is meant to please the people, but its power is no less. The South must yield to the North, and the North to the South, or the union will break apart. If disagreements arise, it may become necessary to consolidate into a kingly power to maintain unity. At the worst, we must keep the links together, for division would be disastrous.
Every leader has their challenges. Poor kings must provide for their people and satisfy their officers and soldiers, who always want something more. Yet we’ve had our great leaders—Father Adams among them—and we will be pleased with our present king in due time. Patience is key, and the majority will find satisfaction.
 
Definitely not a troll, man was both tremendously retarded and incredibly lucky. Classical example of a DSP-style pigroach centuries ahead of his time.
Then I prefer the term pimproach since he was spectacularly rich, likely didn't ever beg and probably didn't snort either.
 
Upon arrival in the West Indies with a boatload of bed warmers the locals were ecstatic. They desperately needed ladles for the local molasses industry and these would do nicely. Dexter sold his bed warmers ladles for a tidy sum and head back to Newburyport.
To be pedantic, from what I remember it wasn't Dexter who sold them off as ladles, but the captain of the ship who just so happened to be really savvy.
 
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