The Inspiring Tale Of America's First Dumb Trashy Millionaire

Started From the Bottom ... Then ... Kind of Stayed There

 In the fahkin cold Boston winter of 1748, Timothy Dexter was born. At a time when most Americans were the British's first unit of peasants, you get in their real-life real-time strategy game of colonialism, Dexter's early life was not much different. Born into modest means to a family of workers, he joined alongside and quickly fell into the leatherworking trade. Dexter quickly climbed the ranks and became pretty damn good at colonial leatherworking, which one would imagine just meant that he was good at running some horrific rusty contraption that twisted cows around like a zoodle slicer for their hide.

As Boston's premier guy at pulling leather off of cows like it was string cheese, Dexter started to set his sights on the one thing that always drove him even more abhorrent cow mutilation: status. The first step to achieving this for Dexter wasn't hard work or networking; it was to marry into some cash. Nobody was better for that job than Elizabeth, a freshly-widowed self-starter who was previously married to one of Dexter's fellow cattle peelers. Though we don't know for sure that Dexter's fellow leatherman ended up in the great iron cow grater through a gentle push, we do know that Dexter was now well on his way to joining the ranks of the wealthy elite. Even if they were about to do everything possible to deny his entry.

Pulling the Colonial RV into the Nice Part of Town

 Now that Dexter had married into money and gotten his fill of cow sheering, he was ready to join the nation's early elite. Despite the rest of the neighborhood's outright disgust in just about everything Dexter, he moved into Boston's Charlestown neighborhood. Surrounded by the likes of John Hancock and other wealthy nobility, they were instantly turned off by Dexter's "low" status as a commoner not fit to join their ranks. Here's the thing about Dexter, though, he simply does not take social cues, so he just plopped down in a house in the middle of them all. Driven by nothing other than his full determination to validate himself through wealth and status, Dexter essentially bought an NFL team just to put himself on the field in one game. Will he get tackled so hard that he turns to dust and bones like an early game skeleton in an RPG? Of course. But will he also be able to say he stepped on an NFL field? Hell yes.

Not satisfied with merely living beside the elite, Dexter wanted to have one of those cool titles like the rest of them would get at the time. Shit like "Purveyor of County Riches," and "Battle Governor of Tobacco and War." After incessant pestering, they relented and gave him the title, "Informer of Deer," whose job was just to like, "Watch for Goddamn deer and report back if you see any deer ... or ... whatever." Knowing that no deer had been spotted in Dexter's area of surveillance for nearly two decades, the actual elite were satisfied with the bestowing of this worthless title onto a man who was just so pumped to even have one to begin with.

Accidentally Moving into a Wealth of Opportunity

With the upward trajectory of Dexter's life in full swing, it was his ability to seemingly fall ass-backward into piles of cash despite the lack of any skill that brought him the riches he became known for. The first, and the one that set the tone for everything to follow, was his directionless speculation on American money. The Continental dollar was one of our first attempts at making money, and ... we weren't that good it turns out. A comical failure to the point of becoming a punchline at the time, Dexter made a ludicrously risky and stupid decision to hoard up the currency at its lowest possible value on the slim chance that it may one day be reinstated as the dollar of choice for this great new country. Though, of course, this never happened, Alexander Hamilton did work the constitution to allow for the trade-ins of these bills for 1% of face value and, overnight, Dexter became filthy rich. Despite having zero intention of playing the game how it worked out for him. 

This is a version of hitting the jackpot that is, more or less, a situation where the Monopoly Man was discovered to be sending unsolicited DMs of his dick to Professor Plum, then disgraced, Monopoly went out of favor, so you go out and buy up every board game at a fraction of the cost to stockpile on the money in there in hopes that one day it is recognized as real money and, against all odds, it happens, and you're rich because the Monopoly Man couldn't stop putting his monocle on his hog and sending it to the three of the four Hungry, Hungry Hippos to not enjoy.

Confident that he would be accepted into the social circles that he so dreamed of, Dexter was soon crestfallen to learn that his new "earned" super wealth did not impress the blue bloods in any real manner. They still saw him as a crude, ignorant, loud man who had only gotten fortune to this point out of luck, rather than the most essential skill that nearly every wealthy person in America has in their back pocket: rich as hell mommy and daddy to prop them up.

Dexter now knew that if his speculation on a comically-worthless form of money didn't impress them, then nothing would. He then set out to make the only move left when it comes to signaling to the world that you're rich as $$$hit: building a heinous estate that's filled with tacky trash. So Dexter bought some land.

The Country's First McMansion

Dexter packed up the Colonial truck with all of his shit from the crib in Charlestown and peeled out of there with his middle finger held high, and whatever late 18th-century version of rap-rock he undoubtedly blasted around town to head for the sea. 

It was along the coast in Newburyport, MA that Dexter figured he'd build his great ode to himself. Perhaps laying the foundation for one of our country's most defining traits, the absolute fact that money can't buy you taste, he erected an absolutely hideous piece of shit beside the shore. Like how winning Powerball doesn't instantly erase your steadfast belief that a sassy Tweety Bird framed print belongs in the dining room of your new 20-room mansion, getting stupid rich by accident didn't prevent him from putting 40 wooden statues on the property featuring his idea of the greatest Americans. The last one being, of course, a statue of the great Timothy Dexter. 

Even better than commissioning artwork of yourself is giving it just completely unwarranted quoting below it, like the one beneath Dexter's wooden bust: "I am the first in the East, the first in the west, and the greatest philosopher in the Western world." This is not far from the great piece of art created at the Zuckerberg property, a figure in his image sculpted out of 300 hundred pounds of aged Hellmann's with a quote below reading: "I am Mark Zuckerberg. I swear I am a human. I am not a robot. Trust me, you guys, I am such a human. I'm a human guy. Not a robot. All human."

Shockingly, the neighbors didn't take a liking to Dexter's bullshit yet again. But even more sad than his increasingly standard way of turning off every community that he attempts to join, is that the place was just so gaudy and pathetic that even his own wife decided she couldn't live there with him. Leaving his neighbors to deal with Dexter's riding a rare purebred Spanish horse around inside, banging off of nude statues of himself, playing a round of indoor golf with marble clubs shrugging as he tees off and saying, "I just can't get my head around why she left ..." 

With his wife out of there, Dexter figured he would live out his own crappy '80s sex comedy, and Dexter Mansion quickly devolved a notorious hotbed for seedy activity.

It's Better to Be Lucky Than Good ... It's Even Better to Be Lucky and Bad

 With his place all to himself and an entire town full of people who hate him, Dexter had to figure out something to do with himself when he wasn't housing sex workers and getting in a quick nine of inside golf. So he did what he does best, stumble into the most unlikely scenarios for absolute riches. These started to pour in when Dexter amassed himself a fleet of shipping vessels. Think of him like that guy in your neighborhood who buys the unnecessary suped pickup truck that sounds like shit rolling down your neighborhood, except this version rolled up a bunch of boats outside the joint instead. 

Obviously not into this guy or the creepy sex mansion to himself he built in their space, the neighbors got tricky. They began to feed Dexter bad tips on business ventures that he could use his cool new boats to complete. Like you going out to let pickup truck guy know that there's a really sketchy corner on a road down the street and that if he floors it into it, cool shit will happen ... but instead of his ride flying off a cliff, his truck does a shitload of awesome flips that are just really fun to experience inside before it lands gracefully into a warm vat of just the good part of s'mores. 

The first tip was from a neighbor suggesting that Dexter load up his shipping vessels with heating pads and send them down to the sweltering West Indie islands. Knowing that Dexter would get down there with this absolutely worthless commodity for them, his neighbors were sure that this would finally bankrupt him. Instead, Dexter went down and found out that, sure, nobody needed heating pads in the tropics, but that he could repurpose the technology as functioning ladles for the large molasses plantation scene and made a killing in the process. When he returned even wealthier than he left, another neighbor tried to feed him a second shitty tip. 

This time, they swore that Dexter would find riches by selling coal to the town of Newcastle. One issue with that, Newcastle was already known for pumping out tons of coal and had absolutely no need for any of Dexter's. He arrived at a coal town with surplus coal, like showing up to McDonald's already experiencing crippling diarrhea, only to find that it had recently been the site of a massive labor strike, and the people there were ready to give up just about any price for coal. Once again, lady luck didn't just smile gracefully on Timothy Dexter; she helped him move, endorsed his most overblown skills on LinkedIn, and gave him a handjob while driving him to his paycheck.

After going undefeated against his neighbor's ploys, mostly because he had absolutely no idea that anybody was plotting against him, Dexter took his business skills even further. Among his other exploits, he once bought a ton of bibles for pennies on the dollar, only to cruise back down to the West Indies and tell the people there if they didn't have one of these bad boys at home that they were going to hell. He returned with no bibles. No conscious. But lots of money. On top of that, he speculated on something even more valuable than worthless currency: whalebones. 

Hoarding up more than 300 tons, he completely took over the market for massive sea creature bones. You know how that goes, it's a story as old as time: the guy who runs the whalebone market is the guy who is truly one step ahead. Dexter was that guy, and he added whalebone and religious scare tactic money to his growing list of unbelievable earning methods. While the rest of us might accidentally land on the right stock once in our lives, he put everything he had into web companies the night before the dot com bubble burst, then right before the markets opened some wise-talking frog in a peacoat came through his bedroom window offering pure gold bars for one share of HotOrNot.com

A Fitting End

One absolute fact of life that fiction has taught me is that if you're a rich ass dude who didn't live a great life, your final years come back to get even some. Whether it's a sled from your youth haunting you or the ghosts of people you wronged hanging around your bed at night, chances are you're going to pay for it in some way. Though, undoubtedly, this isn't how it goes in real life where the mega-rich probably die super sweet deaths in awesomely comfy beds with tons of people helping them and feeding them and keeping them alive way longer than us poors would be able to make it. It seems like Dexter got more of the ghostly sled treatment in his.

During his later years, he tried desperately to find the acceptance and recognition that he was after for his entire time he was actively living in the world around him. In classic Dexter fashion, he of course, got none of this in his later years. Despite trying moves like hiring a poet laureate off the street or attempting to write a book (despite not being able to spell for shit and maybe never reading a book himself) detailing his life and all of the great things he's done, it never quite clicked with the public at large. 

In a final plan to make sure that he was as loved and regarded as he was in his own mind, Dexter faked his own death and held a service at his estate to see what the turnout would be like. In the way that most of the company will show up to a happy hour where they're promised a hot meal, people showed up, but Dexter couldn't stay dead for too long. Eventually, he showed up and found that people met him with a shrug, and life went on just as it was when people did not care if he was dead or alive to begin with.

In his ridiculous final plan before death, he had a massive tomb built where he would be laid forever in the kind of grandiose resting ground so befitting such an important man. Only, when he finally died, the city found some issues with his elaborate tomb and decided it wasn't actually going to let him be rested there, so they just went ahead and put his ass in a standard cemetery like everyone else. In the years following his death, his estate was sold, people moved on, and just about everybody forgot that Timothy Dexter ever lived a day in his life. 

If anything, his tale should be a warning for two of life's great truths: the first being to just live your life as decently as you can while not really worrying so damn much about what other people think of you; but more importantly than that, attempt to get filthy rich despite being a complete jackass and having no real discernable skills to set you up for traditional success. 

Top image:John H. Bufford, James Akin, via Historic Ipswich