4 of the Objectively Worst Bosses in History

4 Max Blanck and Isaac Harris

You can’t talk about the world’s worst bosses without talking about Max Blanck and Isaac Harris, the owners of the Triangle Shirtwaist Factory in Manhattan. The same Triangle Shirtwaist Factory that’s now far better known as a prefix to the word “fire” than as an actual business. Even before tragedy unfolded, it was a quintessential example of what we now would call a sweatshop, with workers clocking 12-hour days as a matter of routine. When a fire started in a rag bin one day, however, it would result in a disaster that would launch labor and worker safety reforms not only across New York City, but the entire country.

As you can imagine, a fire in a rag bin is happier than a pig in shit. Put that rag bin in the middle of a clothing factory full of scrap cloth, and it’s an all-you-can-burn buffet. Luckily, the fire was spotted quickly by a manager, and he attempted to put it out with a fire hose. Unluckily, the hose was rotted and the valve was rusted, and therefore, it was completely useless. The factory had no sprinkler system, which some believe was intentional by Blanck and Harris, who had some questionable business fires in their history, in case they needed to burn it down for insurance money. 

Extinguishment no longer an option, the workers attempted to flee, only to encounter a door that was locked from the outside to prevent stealing. The fire department came, but their ladders weren’t able to reach higher than the 6th floor, which was no help to the 8th floor workers who, thanks to that ghoulish loss-prevention trick, couldn’t meet them halfway. Eighteen minutes after the fire started, 49 workers had burned alive, and another 94 were dead on the sidewalk and in the bottom of an elevator shaft, having jumped to try to escape the flames. 

Blanck and Harris somehow evaded manslaughter charges and ended up settling for $75 per victim — while receiving $400 per victim in insurance money.

3 George Pullman

The tale of train-car tycoon George Pullman is one that a certain couple of futurist billionaires might do well to read after their next transfusion of teenage boy blood. Pullman made a fortune off of luxury train travel, providing passengers with the option to ride his “Pullman cars,” sleeper train cars with top-notch service, food and amenities. These cars provided him with a great need for workers, making him those two unimpeachable words that inspire happy starbursts in the brain of Reaganomics fans and rabid capitalists: Job Creator.

Pullman wasn’t happy only controlling his workers from 9 to 5, however, and followed his vision to create Pullman, Illinois, a company town made up entirely of Pullman workers. How easy and simple, to have your housing handled by your work! Where your houses were inspected for cleanliness, your paychecks were delivered to your door with your rent already carved out and you could be kicked out on 10 days’ notice. True utopia! Or, more accurately and brutally described by Richard Ely as “well-wishing feudalism.” A quote that a couple op-ed writers whose noses are painted Amazon brown would do well to revisit.

Life in Pullman, Illinois became disastrous when, during an economic depression, Pullman cut his workers’ wages, but kept rent exactly the same. Wow, a CEO and a landlord? You’d think he was on a one-man mission to bring back the guillotine. This led to a strike and boycott of all Pullman cars by workers, a cause that was picked up and backed by the American Railworkers’ Union. After a particularly rowdy speech ended with some fires and a derailed locomotive, President Grover Cleveland issued an injunction to end the strike, and sent troops that, gosh, wouldn’t you believe it, escalated the situation, ending with riots and the National Guard killing roughly 30 people. 

To show that he still cared about the capital-W workers even though he’d just ended a strike by murder, Cleveland established a new holiday: Labor Day.

2 George Steinbrenner

Let’s pull back slightly on the history of the labor movement here before I end up on some psycho’s “Pinko Commie Kill List” and cover just a good old fashioned asshole. That man is George Steinbrenner, owner of the New York Yankees and more than a literal handful of World Series rings to go with it. Nobody was arguing with his results. His methods, though, were worthy of a lot more criticism. 

He meddled and micromanaged the team and coaches in a way that must have put stars in the eyes of a young Dan Snyder. He had public feuds with players, most notably Dave Winfield, who he signed to a 10 year contract and then spent all of those 10 years shit-talking. He even hired a guy to spy on Winfield just to give him more ammo to wreck his reputation, a stunt that got him banned for life (later revoked) from being involved in Yankees operations. Maybe most famous was his ban on players, grown adult men with wives and children, from growing any facial hair except a mustache or having long hair, which inspired its own iconic Simpsons line, with a direct dig tacked on at the end. 

But hey, when your legacy is a shitload of championships and getting immortalized in not just The Simpsons, but also Seinfeld, people tend to tint their glasses a little rosier.

1 Hitler

What can I say, the guy was an absolute dictator with a, frankly, appalling record of racial discrimination.