The Worst Writer of All Time

The Almanac Style Guide

Before his death in 1806, Timothy Dexter was hailed as the worst writer of all time.

Born to a poor working family in the British colony of Massachusetts, Dexter took to the fields around age 8 and never received much of an education. By chance, he married a wealthy widow whose equally wealthy friends liked to make fun of him for being a “plain-spoken man”—which is to say a man lacking refinement, an obnoxious boor, a wide-mouthed asshole.

And he was. Timothy Dexter had opinions on everything, most of them quite awful, and his wife’s friends, being narrow-mouthed assholes, liked to tease him with terrible business advice on the hopes that it might “teach him a lesson.”

They told him to ship coal to Newcastle, which was a major coal producer. So he did. It arrived shortly before a coal miner’s strike, and he sold it at a profit.

They told him to ship winter gloves to the Caribbean islands. So he did, where he sold them to warm-port sailors on their way to Siberia.

He sold bed-warmers as molasses ladles, Bibles to missionaries, and invested foolishly in a near-worthless “Continental currency”—which expanded his fortune again when, against everyone’s best predictions, the American colonists defeated the most powerful empire in the world.

Dexter built a mansion, which later became a hotel, and filled the grounds with statues of great men of the age: George Washington, Napoleon Bonaparte, and himself. But try as he might, he could never win the respect of the professional class, who found his arrogance and vulgarity distasteful.

And it was. At one point, Dexter faked his own death just to see who would show up at his funeral. When he noted his wife wasn’t crying, he leapt forth immediately, revealing the hoax, and took a cane to her.

At the age of 50, after amassing a fortune, Timothy Dexter decided he would write a book—about himself. “A Pickle for the Knowing Ones, or Plain Truth in a Homespun Dress” ran to a mere 8,000-and-some words, an essay by modern standards, and was nothing but one long gripe: about politicians, about the clergy, about foreigners, and about his wife, without whose fortune he would have stayed a very poor man.

But the little book’s most notable quality, that for which it is best remembered, was that through all 33,864 letters, there was not a single punctuation mark. No periods. No commas. Nothing. There wasn’t even regular capitalization.

Dexter paid for the printing himself and handed the book out for free, just like any good indie author today. But following the same ridiculous luck he’d experienced his entire life, the damned thing took off, and Timothy Dexter’s tiny monstrosity ran through eight separate printings, despite widespread criticism from the literati that the lack of punctuation made it a grade-school farce.

Alas, the great public beast eats what it wants.

Dexter responded to his critics in typical style in the second edition. He appended an extra page to the book filled with nothing but punctuation—13 lines of it, in fact—“A Nuf,” he said, that his readers could “peper and solt” the text as they pleased.

Some hundred years after Timothy Dexter died, James Joyce played the same trick with punctuation, to widespread critical acclaim, in his book Ulysses, which is often hailed as the greatest English-language novel of the 20th century.

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Writing is a dismal job. As pastimes go, very little can compare. But as a career, well, one could bring home more bacon from a Jewish potluck. Every week, the commercial market finds a new way to kick you in the balls. Your customers are fickle, your colleagues are false and feigning, and the only thing worse than the lot of them is your own feckless pursuit of their praise.

We’re submissives, we writers, strapped and bound without a safe word—or perhaps we’re masochist-priests who believe every stinging, self-inflicted lash rids us of some lexical sin. My characterization was weak and that’s why people didn’t like it. Lash. I was overly cerebral. Lash. I wasn’t writing authentically; I didn’t bleed onto the page.

Cardinal sin. Ten lashes.

The truth is, commercial success has very little to do with “qualitie,” as the case of Timothy Dexter shows. The dark goddess of the market will make a rich man richer just for the giggle but leave Poe penniless in the street. At the time of his death, the astonishing popularity of “The Raven” had made him a household name. He was paid $9 for it, or about $300 today, and the proceeds from all subsequent sales and reprints went to the publisher.

Even after he collapsed in a gutter in Baltimore and died, the publishing market was not done with him. Somehow, Poe’s own personal Salieri, a man called Rufus Wilmot Griswold, who bore Poe a lifelong grudge, was appointed his executor and proceeded to malign him in a series of articles culminating in a biography that painted him as a depraved drug addict. Only then did Poe’s other works get noticed, not because of their “qualitie” but because people got a secret thrill out of reading the work of a notorious madman.

So successful was this hatchet job that even today, some 170 years later, we still think of Poe as a melancholic drug addict even though historians seriously doubt that was the case.

People will respond that the world is not fair. No, hurricanes are not fair. They take worthy and unworthy alike. Commercial fiction isn’t a hurricane. It’s a con. One could wring more honesty from a strip club.

But still we suckle at it. Like every other fool, when our next book is done, we will climb to any perch free of pus and seminal fluid and prostrate ourselves before the dark goddess and beg she take note, if only to smite us again.

Our advice is this. Write what you want to write and how you want to write it. There’s no secret sauce. The Dragon Scroll is empty. Those anointed by Fate will believe they earned it. But Poe and Dexter say otherwise.