The 6 Most Horrific Bosses of All Time

Think about the worst boss you have ever had. Now add psychotic paranoia and murder.
The 6 Most Horrific Bosses of All Time

Think about the worst boss you have ever had. At any point did you find yourself describing him or her as the "worst boss ever"?

The 6 Most Horrific Bosses of All Time

Because you were wrong. There are bosses in the post-slavery era who took the normal "horrible boss" stereotype and raised it to astonishing, horrifying new heights. So just be glad you didn't work for...

George Pullman

The 6 Most Horrific Bosses of All Time


Do you ever dream of making enough money that you can pay (or force) people to act out your video games for you? Well George Pullman basically built a real-life version of The Sims.

The 6 Most Horrific Bosses of All Time

Good or bad? You decide.

Why He Was An Asshole Boss:

Whenever you hear a historical figure referred to as an "industrialist," you know he was pretty shitty to work for. That certainly went for George Pullman, an industrialist who made his fortune in the railroads.

But Pullman wanted to be a father to his employees. An abusive, scary, probably drunken father. So he bought a huge chunk of land and built a town on it for his employees to live in.

The 6 Most Horrific Bosses of All Time

Well, that kind of makes sense. Save on the commute, build a sense of unity. It's the kind of thing that could almost work, if the guy in charge wasn't completely batshit.

Just like some people can't play The Sims for more than an hour before inventing ways to torture the inhabitants, Pullman's town quickly became his own little kingdom-slash-prison. He forbade any free press, public meetings or bars. He would send guys to barge into employees' homes and make sure they were being kept spotless. Anybody who failed to meet Pullman's cleanliness standards were given 10 days to pack up and get out.

The 6 Most Horrific Bosses of All Time

But if the others didn't like it, they could just leave, right? Well, Pullman started paying his employees in what he called Pullman Scrip, which could only be spent in the town and could not be exchanged for actual money.


And while running your own town according to your crazy fuck rules is kind of terrifying just on the face of it, things only got worse when the company started going downhill and everyone's wages were cut. To compliment the imaginary wage cuts, rent and the imaginary prices at the company stores were kept right where they were, squashing employees between a financial hammer and anvil. The situation eventually exploded into a strike that got so out of control that federal troops had to be brought in.

How much did the workers hate Pullman? When he died, they had to bury his body in a steel and concrete vault, which was itself buried under a few tons of concrete. Why? Because--and we're not making this up--they were afraid that employees would dig up and beat the shit out of his corpse, otherwise.

J. Edgar Hoover

The 6 Most Horrific Bosses of All Time


J. Edgar Hoover was the first director of the FBI, from 1935 until 1972, and he was crazy for every minute of it. Not coincidentally, Hoover's also the reason FBI directors are limited to 10-year terms of service.

The 6 Most Horrific Bosses of All Time

Why He Was An Asshole Boss:

The world may never know exactly how insane J. Edgar Hoover was. That's the thing about holding an unelected position in an organization specializing in undercover work and keeping rooms full of secret files with the demand that they be destroyed upon your death. Stories have been boiling up about the man pretty much from the moment he expired, each more bizarre than the last. Nobody knows which are true, but they all paint a picture of a man about five minutes away from a shooting rampage.

The 6 Most Horrific Bosses of All Time

One biography says he kept FBI employees on call 24 hours a day to just do random shit around his house, like repair his lawnmower. When he found a small animal turd on his patio, he demanded that agents take it to the lab to analyze it, completely sure he was being stalked by a wild animal. He then allegedly had them set a trap on the patio, which promptly killed the neighbor's cat.

He also loved to scrawl almost unreadable notes and instructions in the margins of memos. Then when one memo came his way with barely enough room on the edges for him to write in, he scrawled, "WATCH THE BORDERS."

Watch The Borders

Nobody had any clue what that meant, and they were too terrified of the crazy old bastard to ask him. So, they put out word to the Border Patrol to watch both the Canadian and Mexican borders for anything unusual. They arrested American Communist Party leader Gus Hall during the crackdown. A week later, staff finally figured out that "WATCH THE BORDERS" meant "leave more room in the margins of these memos because I like to write stuff in them."

Also, he apparently had a file of nude photos. Not of porn models; of everyone. He had nude pictures of Eleanor Roosevelt. Why? Just in case.


He is said to have monitored every aspect of agents' lives, telling them where they could and couldn't live, what clubs they could and couldn't join and what to wear. He allegedly fired agents because he thought their heads looked too small.

The 6 Most Horrific Bosses of All Time

But life under Hoover wasn't all Michael Scott-esque lovable eccentricity. Melvin Purvis (as in, "the guy Christian Bale plays in Public Enemies") pissed Hoover off by having the nerve to track down three of the most infamous gangsters in American history (Baby Face Nelson, Pretty Boy Floyd and Johnny Depp's John Dillinger) and not give Hoover the credit. Hoover harassed Purvis until he left the FBI, then supposedly went around trying to sabotage all future jobs Purvis tried to get in the years after.

Wait, you're still picturing Eleanor Roosevelt naked, aren't you?

Henry Clay Frick

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Henry Clay Frick was the Chairman of Carnegie Steel, and also proud owner of the titles "the most hated man in America" and "Harry Cock-Bag."

The 6 Most Horrific Bosses of All Time

Not to be confused with this hairy cock bag.

Here's a fun story about Frick: He started a fishing club for himself and his wealthy friends, buying up a lake in Pennsylvania, just for them. Its dam was constantly leaking, but not wanting to spend the cash to fix it, he let it go until the day it broke and flooded a town, killing 2,000 people.

At which point Frick admitted responsibility and... oh, wait, no. He hid behind his lawyers and spent the money on legal fees instead.

Why He Was An Asshole Boss:

In 1892, the world was just figuring out that everything was more awesome when it was made of steel. Prices were going up and the steel producers of the world (like Andre Carnegie and Mr. Frick) were living in houses made of bling. It just so happened the union's contract was up at a plant Frick was in charge of, and they came to the table asking for a raise.

Frick lit a cigar with a million dollar bill and counter-offered... a 22 percent pay cut.


When the union rejected the deal, Frick's counter-offer involved locking out workers, then installing sniper towers around the plant and cannons that could shoot boiling hot liquids on anyone who approached. He also put up a huge barbed wire fence, though that kind of seems redundant with those first two in place.


Vehicles and maniacal lust for power sold separately.

Thousands of angry employees picketed outside the building, and Frick decided to truck in some nice low-wage workers to replace them. Of course there was the problem of the giant crowd of screaming men outside the plant, so Frick hired 300 Pinkertons--old timey mercenaries with a terrible name--and unleashed them on the crowd.

The 6 Most Horrific Bosses of All Time

All hell broke loose. It turned out the striking workers had guns, too, and dynamite, and a cannon. Several people were killed on each side, and dozens more wounded, before once again the military intervened to break things up.

Figuring that this Frick asshole was the real problem, a few weeks later a guy broke into Frick's office and shot him in the neck. Twice. At this point Frick rose up (presumably laughing deeply while his wounds suddenly healed before the assassin's eyes) and fought back. The cops came and arrested the assassin, and Frick was back to work in a week. And by "back to work" we mean he quickly fired 2,500 workers, and halved the pay for the ones who were left.

The 6 Most Horrific Bosses of All Time

Frick wouldn't die until 27 years later, when somebody presumably remembered to put a stake through his heart.

William Bryant and Francis May



William Bryant and Francis May were the owners of the Bryant and May Match Company. For quite a while, if you were a smoker you had Bryant and May matches in your pocket. Also the blood and tears of children.

BRYANT&MAY LTD MATCH MANUFACTURERS' By Te Apnointment HM the KING 33 Awards ForExcellence

Why They Were Asshole Bosses:

Look, if you ever have a chance to take a job that requires you to first travel in a time machine to Victorian era England, don't do it. This is Scrooge era here, when filthy children roamed the streets, eating rats and doing adorable song and dance numbers.


So how shitty of a boss did you have to be to become the subject of huge public backlash in those days? Let's examine the Bryant and May method.

First, you hire nothing but young, teenage girls. There were plenty of them around, they had no other opportunities, and they weren't likely to beat you down with lead pipes when they got fed up with your shit. You work them 12 hours a day, and pay them in the neighborhood of four shillings a week (the equivalent of $20... in today's money).


The exact amount Corey Feldman was paid to be in The Lost Boys sequel

Since forcing the workers to scrape by on quite a bit less than what it costs to buy food still wasn't keeping morale quite low enough, they imposed a series of petty fines for a long list of offenses--everything from going to the bathroom without permission, to having dirty feet. When one girl let a machine jam up rather than have it tear off her finger, she was told the machine was more important, dammit, and to never let it happen again. When another girl did get her hand mangled, she was given the boot. Can't make matches one-handed!

However, Bryant and May couldn't help but notice the other match companies were still making more money. What were they doing wrong? Clearly they weren't abusing their employees enough... was there some kind of torture device they could be using? Maybe if they just let wild badgers run loose on the production floor?

The 6 Most Horrific Bosses of All Time

They had a better idea. They had been making their matches with the extremely flammable but otherwise safe red phosphorous. But there was this other kind, white phosphorous, that was way cheaper. And there was absolutely no downside.

Oh, except it would literally eat your face off when you handled it.

The 6 Most Horrific Bosses of All Time

Seriously. They called the condition phossy jaw. It was caused by breathing the fumes for too long. The symptoms start with toothache, which led to swelling, abscesses and then a putrid discharge caused by your jaw bone actually rotting inside your head.

Then your jaw would actually start to glow green. It fucking glowed. The only treatment was jaw amputation, which had to be done before organ failure killed the victim.

The 6 Most Horrific Bosses of All Time

Keep in mind, Bryant and May knew this; white phosphorous matches and the corresponding side effects had been around for decades. The girls at the factory finally went on strike, figuring horrifying deformities were the final straw. The whole "glow in the dark face-rot" won the sympathy of labor activists at the time, and the women eventually won the right to experience something less than David Cronenberg-levels of horror at their workplace.

The Bryant and May company, of course, stayed in business for decades and made its owners huge amounts of money.

Max Blanck and Thomas Harris



Max Blanck and Thomas Harris were the owners and operators of the Triangle Shirtwaist Company, which made lady's blouses. Why blouses are called "shirtwaists" is lost to time, if by "time" you mean us not caring enough to go check. Did they only make the waist part of the shirt? We'll never know.


Why They Were Asshole Bosses:

Blanck and Harris employed an almost entirely female workforce for the same reasons as Bryant and May: young, many of them immigrants, all with nowhere else to go. They paid six or seven dollars a week (again, shit money even in 1909) and when workers walked out demanding better conditions, the pair hired thugs to beat the crap out of them. When the garment workers' union finally came to an agreement with other manufacturers, Blanck and Harris said hell no.

On top of all this, it seems like a minor thing that they also locked one of the main factory exits from the outside, to supposedly prevent theft by employees. Minor, you know, unless there's a fire. But why would there be a fire in a factory full of machines, strips of dry cloth, tissue paper and smokers? Where there had been fires twice before?


On March 25, 1911, the inevitable happened. Some women made it out before one exit filled with smoke and flame. Others made it onto the fire escape, which collapsed. The rest were trapped inside, banging on that locked door, while they were cooked alive.

All told 146 people died, the worst fire in New York history (a record that would stand all the way until 9/11).

Blanck and Harris were charged with manslaughter. Luckily for them they had way more money than the plaintiffs, and they hired Max Steuer, the Johnny Cochran of his day. He tore apart the testimony of the survivors, hinting that the whole thing was a conspiracy by the evil labor unions, and that no one could prove the door was actually locked. Sure, they found the lock in the burned out rubble, still very much in its locked state. But couldn't it have been tampered with? By the unions?

The 6 Most Horrific Bosses of All Time

The unions!

Blanck and Harris got off. But Blanck was arrested two years later for--get this-- locking his fucking workers inside another factory. Holy shit!

They had his ass now! Justice would be served! Oh, wait, no. He was fined $20.

The 6 Most Horrific Bosses of All Time

But wait! Twenty-three families did successfully sue over the Triangle fire and won... $75 each. So, that's sort of justice, right? That's almost 2,000 bucks right there?

Wait, did we mention that Blanck and Harris filed a claim with their insurance after the fire? And got $60,000?

Henry Loeb

The 6 Most Horrific Bosses of All Time


Mayor of Memphis, Tennessee, 1968 - 1971. Unemployed jackass, 1971-?

The 6 Most Horrific Bosses of All Time

Why He Was An Asshole Boss:

If there's one thing a city thrives on, it's a rich subculture of homosexual artists who will paint murals on all the downtown buildings. Next in line is the services it provides. And no service is more vital in the sweltering, stanky South than getting the trash off the streets, so you'd think the mayor would want to keep the sanitation workers happy at all costs.

The 6 Most Horrific Bosses of All Time

Does this look like the type of man you'd want to cross?

Unfortunately things worked a little different in the late 60s, and things worked way different in Memphis. Especially when the mayor was the white, wealthy Henry Loeb, and the sanitation workers were black.

So, it's one thing to do job that still paid minimum wage after 15 years, and involves picking up trash in a city that didn't require any kind of bags or cans at all, so people could just fling the shit onto the curb as part of their "the negroes will get it" system.

The 6 Most Horrific Bosses of All Time

A system supported by many .

But it's another thing to do the job for a boss like Loeb, who layered on one arbitrary rule after another, purely out of dickishness. Workers weren't allowed to stand in the shade of a tree. They got 15 minutes for lunch. But, worst of all, were the trucks; the old, broken-down machines were ridiculously unsafe, as employees told Loeb again and again.

Finally, one of those trucks malfunctioned and crushed two workers to death, pulverizing them into the garbage.

The employees went on strike, and the city council immediately decided that what they had been doing was pretty shitty even by the standards of the late 60s South. They voted to give in to the union's demands, and everyone lived happily ever-

-Oh, wait, no. We forgot about Loeb. Loeb rejected the council's decision, then sent in police to fire mace and tear gas at demonstrators.

The 6 Most Horrific Bosses of All Time

At this point the sanitation strike became a national civil rights cause, bringing a certain Dr. Martin Luther King, Jr. to town, along with tens of thousands of protesters. Loeb declared Martial Law, and brought in 4,000 National Guardsmen.

King addressed the sanitation workers on April 3rd, 1968. That, in fact, is the reason he was still in Memphis the next day, on April 4th, 1968. The day he was assassinated.

The 6 Most Horrific Bosses of All Time

Yes, the world is basically one big orchestra of assholes, playing in concert.

Needless to say, in the wake of Dr. King's assassination, Loeb and the city finally gave in to the striker's demands. Then they reneged on the deal, and the workers had to threaten a second strike before Loeb was finally forced to give in, his well of douche having finally run dry.

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For more jobs that are downright awful, check out 6 Dream Jobs That Would Actually Suck and The 5 Most Overrated Jobs Of All-Time.

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