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"?

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...

#6. George Pullman


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.

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.

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.

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.

#5. J. Edgar Hoover


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.

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.

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."

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.

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?

#4. Henry Clay Frick


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."

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.

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.

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

Recommended For Your Pleasure

To turn on reply notifications, click here


The Cracked Podcast

Choosing to "Like" Cracked has no side effects, so what's the worst that could happen?

The Weekly Hit List

Sit back... Relax... We'll do all the work.
Get a weekly update on the best at Cracked. Subscribe now!