Benjamin: The Slave Who Turned His Master’s Cigars into His Coffin on Election Night | HO!!

The year was 1872, and the air in Richmond hung thick with summer rot and coal smoke when Dr. Edmund Vorters opened an envelope postmarked from Boston. Inside was a seven-page letter, written in a hand so precise it looked engraved. The first line froze him cold:
I killed him. I am not sorry.

By the time he reached the end, Vorters’ hands were trembling. The confession he held was more than a murder. It was proof of a plan so intelligent, so patient, and so terrifyingly deliberate that it had gone undetected for twelve years — a secret rebellion disguised as natural death, carried out through the very crop that had built the South’s empire.

The letter was signed simply:
Benjamin Freeman — formerly property of Colonel Marcus Hafford of Buckingham County, Virginia.
And before he burned that letter to ash, Dr. Vorters understood he was holding evidence of one of the most brilliant acts of resistance in American history.

I. THE TOBACCO MAN

To understand Benjamin Freeman, you have to go back to the night Abraham Lincoln was elected president — November 6, 1860 — and to the plantation where one man decided he’d rather be a murderer than remain property one more day.

Buckingham County lay in Virginia’s tobacco belt, where the soil ran dark and rich and the smell of curing leaves clung to everything. Colonel Marcus Hafford owned twelve thousand acres and ninety enslaved people. Among them was a man everyone called Benj: quiet, careful, unremarkable in every way that mattered to white people — which was exactly how he wanted it.

He’d been born there in 1826. His mother, Celia, worked in the main house until fever took her when he was twelve. Before she died, she gave him a weapon more dangerous than any whip or gun: literacy. She’d stolen a Bible and scraps of newspaper, teaching him to read by candlelight and making him swear never to reveal his secret. Knowledge will get you killed, she’d said. But it’ll also set you free.

After her death, Benjamin kept learning. He read anything he could steal: medical texts, chemistry manuals, botany treatises, plantation ledgers. From a tattered agricultural journal, he learned that tobacco contained a substance called nicotine — a stimulant in small doses, a deadly toxin in large ones. The difference between pleasure and death, he realized, was simply quantity and patience.

By thirty, Benjamin was the plantation’s master cigar roller. His cigars were the colonel’s pride — aged in rum, wrapped in fine leaf, smoked by the most powerful men in Richmond. That skill gave him access: to the barns, the stores, even the colonel’s private study. Access, he knew, was opportunity.

II. THE MASTER AND HIS MASK

Colonel Marcus Hafford was fifty-three that fall — tall, silver-haired, self-satisfied. He called himself a “progressive” slaveholder because he allowed garden plots and seldom whipped anyone himself. He believed these gestures made him enlightened. “I’ve always treated you fairly, haven’t I, Benj?” he liked to say, cigar smoke curling between his teeth. Benjamin always answered, “Yes sir. Very grateful, sir.” Inside, his rage burned so hot it could melt iron.

To the colonel, fairness meant being worth $1 800 on an inventory sheet — less than a carriage horse, less than the chandelier over the dining table. Fairness meant being owned.

But Benjamin had learned the art of invisibility. He played the loyal craftsman while watching every habit, every weakness of the man who owned him. And he began to see how power made people careless.

The colonel’s greatest pleasure was his cigars. He smoked them morning and night, bragging that no one in Virginia rolled finer tobacco than his “boy Benj.” That vanity was the opening Benjamin needed.

III. ELECTION NIGHT

The days leading to Lincoln’s victory felt electric — tension humming through Virginia like static before a storm. Planters whispered about secession. Enslaved people whispered about hope. The colonel threw a dinner party two weeks before the vote, filling his dining room with the county’s elite. Benjamin served the wine, his face a mask, as men debated whether a Republican president would end their world.

When one guest warned that Lincoln’s election might “ignite the South,” the colonel snorted. “The man’s a lawyer from a barnyard. No backwoods abolitionist can change what God ordained.”

Benjamin refilled his glass and made a decision: the colonel’s certainty would kill him.

For months he’d been experimenting, soaking discarded tobacco stems in liquor to draw out their nicotine, distilling the syrup until a single drop could kill a dog. Mixed sparingly into cigars, the poison caused nausea — nothing alarming. A little more, and it could stop a heart within hours. Benjamin had already been testing small doses on his master for three months, watching him grow paler, more short-tempered, more easily winded. On Election Night, he would finish the work.

That evening, Lincoln’s victory was announced. In Buckingham County, men shouted in outrage, drinking themselves blind. When the colonel’s carriage clattered up the drive near 2 a.m., Benjamin was waiting.

Hafford burst through the door, red-faced and shaking with fury. “That railsplitting bastard won!” he roared. “Bring my cigars. The good ones.”

Benjamin fetched the humidor — not the usual box, but its twin, identical in every detail, lined with Spanish cedar and filled with cigars brushed in a double coat of concentrated nicotine. He set it on the desk beside the brandy.

The colonel lit one, inhaled deeply, exhaled a ribbon of smoke. “At least I still have these,” he muttered. “The best damn tobacco in Virginia.”

Benjamin stood by the door, hands folded, watching the smoke curl like a ghost around the man who had owned his life.

By the third cigar, Hafford’s words slurred. “You’re a good negro, Benj… treated you fair…”
“Yes sir,” Benjamin said softly. “Very grateful, sir.”

By the fourth, the colonel’s skin had gone gray. Sweat rolled down his temple. His heartbeat raced wildly, then faltered. “Something’s wrong,” he gasped. “Fetch… the doctor…”

Benjamin didn’t move.

Hafford’s eyes met his — confusion, then recognition. “You… you did this.”

Benjamin said nothing. He simply watched as the man’s chest heaved once, twice, and stilled. Four cigars burned to ash in the tray. Outside, the first birds began to sing.

IV. CLEANUP

Benjamin worked quickly. He replaced the poisoned cigars with ordinary ones, arranged the scene to suggest a night of drunken excess, then returned to his narrow cot behind the kitchen and lay awake until dawn. When the maid found the colonel’s body, the house erupted in screams. Dr. Nathaniel Grimby pronounced the death apoplexy brought on by “overindulgence and agitation.” Everyone accepted it. Powerful men died that way all the time.

At the funeral, rain soaked the red Virginia clay. The minister praised the colonel’s “kindness to those in his charge.” Benjamin stood among the servants, head bowed, listening to the lies and feeling nothing at all. The man they eulogized had never existed.

Within weeks, the plantation began to unravel. Without a will, ownership was uncertain. The overseer, Silas Portwood, took charge — until he, too, was found dead at his desk, a half-smoked cigar in hand. Dr. Grimby made the same diagnosis. This time he scribbled a note in his journal: Two men dead. Similar symptoms. Possible connection?

Benjamin said nothing. He was already planning his escape.

V. THE GIFT THAT KEPT KILLING

He didn’t run right away. Running blind was suicide. Patrols scoured every road; bounty hunters tracked with dogs. He needed time — and patience he had in abundance.

He spent the winter of 1860 preparing a final act of vengeance. Using the same extract, he treated dozens of cigars, sealed them in polished boxes, and hid them throughout the property — in the study, the overseer’s office, the barn lofts. Anyone who bought the Hafford plantation would inherit not only its wealth but its doom. It was revenge designed to outlast him.

On a moonless night in February 1861, he unlocked the colonel’s study with a key he’d forged from a wax impression. By candlelight he memorized every document: the deeds, the slave inventories, the colonel’s business correspondence. He noted arms shipments, Confederate sympathizers, secret caches of supplies. When he found his own name listed — Benjamin, age 34, tobacco specialist, value $1 800 — he felt something in his chest harden forever.

Three days later, he vanished.

VI. THE MAN WHO DISAPPEARED

The next morning, the cook sent a boy to fetch tobacco. Benjamin’s room was empty, his bed cold. The overseer’s replacement organized a search. Nothing. He’d melted into the night like smoke.

Catherine Hafford, the widow, couldn’t understand. “Why would he run? We treated him well.” Her bewilderment was almost touching. She truly believed comfort was freedom.

Bounty hunters scoured the roads north. They found no trace because Benjamin hadn’t gone north by road. He’d gone west into the Blue Ridge, following slave-run networks of Quaker farmers and free blacks who moved fugitives toward Pennsylvania. By July 1861, he was in Boston, alive and free under a new name: Benjamin Freeman.

There he found work unloading ships, then blending tobacco in a warehouse. The irony wasn’t lost on him. The crop that had chained him now fed him. He saved his wages, rented a room, and eventually opened his own shop on Beacon Street. Freeman’s Tobacco. The sign said everything.

VII. THE CURSE OF THE PLANTATION

Back in Virginia, men kept dying.

In 1862 a Richmond speculator bought the Hafford property. Six months later, he was found slumped in the study, lips blackened, ashtray full. Dr. Grimby examined him, disturbed by the repetition. He began keeping notes — detailed ones.

“Symptoms consistent with nicotine poisoning,” he wrote. “But at impossible concentration for normal tobacco.”

No one believed him. People blamed the house, the air, curses. By 1863, no buyer would stay more than a season. The mansion became known as the cursed plantation.

The war came and went. The Confederacy fell. The fields grew wild. And Benjamin Freeman sold fine cigars to Boston gentlemen who would never imagine the man behind the counter once turned tobacco into death.

He married a seamstress named Harriet in 1864. They had a daughter, Celia. He became a deacon at his church, a pillar of his community. To neighbors he was quiet, respectable, unremarkable — which was exactly how he wanted it. Only in dreams did he return to that Virginia study, the glow of cigar ends, the sound of a man choking on smoke and pride.

VIII. A DOCTOR’S DISCOVERY

In 1868 a Union veteran named Harold Graham bought the “cursed” plantation, scoffing at superstition. He was a cigar aficionado; when he discovered several sealed boxes in a hidden cabinet, he considered them a prize. They smelled rich, aged, perfect.

By autumn he was dead — the same gray skin, the same half-smoked cigar in his hand.

This time the attending physician was Dr. Edmund Vorters, a young pathologist from Richmond. The pattern bothered him. He took several cigars back to his lab. Chemical tests revealed nicotine levels four to five times normal, unevenly distributed — unmistakable evidence of tampering.

Vorters compared notes with Dr. Grimby’s old journals, now dusty in a drawer. The symmetry of deaths stretched back to 1860, always involving cigars, always in that same study. One name appeared in the earliest entry: Benjamin, tobacco specialist.

“What if he didn’t just flee slavery?” Vorters mused. “What if he fled the scene of a perfect murder?”

IX. THE LETTER

He wrote up his findings but the sheriff, unsure how to prosecute a ghost, filed them away. The story might have ended there — until the summer of 1872, when the envelope from Boston arrived.

Inside was Benjamin Freeman’s confession.

Sir,
I understand you have investigated the deaths at the former Hafford plantation. Your suspicions are correct. My name is Benjamin Freeman, once property of Colonel Marcus Hafford. I killed him. I also killed Silas Portwood. I am not sorry.

Page after page, Benjamin detailed his methods — the chemistry, the testing, the months of incremental poisoning.

The cigars I prepared for that election night merely finished what had already begun. I left others hidden so that men who profited from that land might share its curse. Whoever smoked them would die as he died — slowly, proudly, believing himself untouchable.

He described his escape, his life in Boston, his marriage, his respectability. And then came the line that made Vorters’ heart falter.

I write not from guilt but from truth. I proved that the enslaved could think, plan, act with patience and precision. I proved we were never the simple creatures they believed. My revenge was my proof of humanity.

Vorters sat for hours, the pages trembling in his hands. He’d lived through the war. He’d seen slavery’s rot up close. Could he really condemn this man?

He stood, walked to his fireplace, and fed the pages one by one to the flames.

The law could do nothing now. And perhaps, he thought, it shouldn’t.

X. ASHES AND LEGENDS

The Hafford plantation decayed into myth. Locals said ghosts haunted its ruins, that the land itself was poisoned. Among freedmen, quieter stories spread — of Benj the tobacco man who made his master smoke death. Told in whispers, the tale was equal parts horror and pride.

“He showed them we could think,” an old woman said years later. “He showed them we could wait.”

Benjamin Freeman lived another thirty years in Boston — husband, father, tobacconist, church deacon. He died in 1894 at sixty-eight. The Boston Globe called him “a respected businessman.” A black newspaper in Richmond printed a different obituary: He leaves behind a legacy some will understand and others never will.

XI. THE UNEARTHING

The truth might have ended there if not for accident. In 1930, a local historian cataloging old medical papers found Dr. Grimby’s journals, filled with notes about mysterious cigar deaths. He published a short piece in an obscure Virginia medical review. It went mostly unnoticed — until 1958, when a graduate student researching plantation medicine stumbled on it and dug deeper. She found Vorters’ report, cross-referenced census records, and uncovered a Boston tobacconist named Benjamin Freeman.

Her dissertation quietly suggested an enslaved man had engineered a string of poisonings. No one paid much attention until 1992, when historian Ruth Ellison rediscovered the paper and turned it into a book: Poison Tobacco: The Hafford Plantation Murders.

The story went viral before “viral” existed — reprinted, debated, adapted into documentaries and podcasts. Some called Benjamin a serial killer. Others called him America’s first chemist of freedom. Descendants of enslaved families from Buckingham County began sharing letters and oral histories that confirmed what he’d done.

One handwritten note, dated 1895, preserved in the Virginia Historical Society, reads:
What Benj did, he did for all of us. His revenge was our vindication.

XII. WHAT IT MEANT

Drive through Buckingham County today and you’ll see soybean fields where tobacco once grew. No trace of the mansion remains. But if you stand there at dusk, the wind still smells faintly of smoke.

Benjamin Freeman’s story survives because it refuses to fit neatly into anything. He was both murderer and liberator, villain and proof of humanity. His act didn’t free a nation, but it shattered the illusion that the enslaved were powerless.

He turned his master’s luxury into a weapon. He made the symbol of Southern pride — the cigar — into a coffin.

He proved that knowledge was power, that patience could be deadlier than rage, and that even in bondage, the mind could remain free enough to plot justice in the slowest, quietest, most devastating way imaginable.

Was it murder? Yes. Was it justice? Maybe. Was it human? Absolutely.

The colonel died believing he was smoking victory. What he inhaled was history catching up.