10 Horror Stories about the Worst Bosses Ever

bad boss stories

Horrible bosses like Miranda Priestly, Bill Lumbergh, David Brent and Bobby Pellitt don’t just exist in Hollywood – they exist in real life, too. And I’m sure many of you can attest to that from first-hand experience.

But if you’re looking for a little pick-me-up by reading about people who are far worse off than you, then you’ve come to the right place.

Here are 10 horror stories about the worst bosses ever – some are just as bad as any horrible boss you’ve had the displeasure of working for; others make Hitler look like a really nice bloke.

1. Alejandro Rhett

Alejandro RhettFashionista

Layoffs are often a necessary evil for the survival of a company, but the last thing someone expects after being laid off is to be mocked about it on social media. Which is exactly what happened to 175 workers who were let go from financially troubled fashion company J.Crew in June 2015.

After breaking the news to the unlucky employees, Alejandro Rhett (the vice president of men’s merchandising) went on to celebrate the axing with three work buddies at a West Village bar in New York City, posting alcohol-fuelled party pics on Instagram with captions of Hunger Games references. The incriminating posts have since been deleted, though one photo featured the hashtag ‘#maytheoddsbeeverinyourfavor’.

Mr Rhett got a taste of his own medicine, though, and was reportedly fired over the incident.

2. George Pullman

George PullmanBrittanica

George Pullman was an American engineer and industrialist who lived in the 19th Century. He designed and manufactured the Pullman sleeping car and had a private town specifically built for his employees and their families, complete with a church, library, shopping centres and a sewer line. Sounds like a pretty good boss, right?


Other than the fact that employees were paid below-subsistence wages in ‘Pullman scrips’ and not real money (which, by the way, could only be used in town), he implemented wage cuts when business faltered but did not lower rent (which was automatically deducted from workers’ pay packages). He was also a stickler for cleanliness, so much so that he would send inspectors to employees’ homes – who were fired on the spot if they didn’t meet Pullman’s standards.

So, no. He wasn’t a good boss. In fact, he was so bad that his family had him entombed in a concrete and steel crypt after he died because they feared people would desecrate his corpse!

3. Rolandas Milinavicius

Rolandas MilinaviciusAJC

Asking for a much-deserved raise can often be an awkward, intimidating and nerve-wracking experience, to say the least, but no one expects it be their final experience. Sadly, that was the case for Inga Contreras and Martynas Simokaitis.

The two Lithuanians were employed by Rolandas Milinavicius (also from Lithuania) at RM Auto International, a car dealership based out of Atlanta, Georgia. They weren’t happy about their pay and had several discussions with Mr Milinavicius about a raise until he finally snapped on 27 July 2007, pulled a nine-millimetre handgun from a file cabinet and shot them both in the head.

He turned himself into the police two days later and confessed to the killings, saying that his company was having financial difficulties and that he was ‘under a lot of stress’.

4. Naomi Campbell

Naomi CampbellVanity Fait

Supermodel, actress and singer Naomi Campbell can also add ‘convicted assaulter’ and ‘worst celebrity boss’ to her rather impressive CV. In fact, between 1998 and 2009, she was accused of committing acts of violence against employees, associates and other individuals a total of 11 times.

It all started in September 1998 when she assaulted her personal assistant Georgina Gatanis by grabbing her by the throat and hitting her on the head with a mobile phone. She admitted to the assault in 2000, expressed her remorse and agreed to attend anger management classes.

But those anger management classes didn’t really work: by 2006 she was accused of physical abuse by eight other employees and associates, and in 2007 pleaded guilty to throwing a mobile phone at her housekeeper (this time identified as a BlackBerry). She was sentenced to attend anger management classes (again) and perform five days of community service (she reportedly served the final day of her sentence wearing a silver-sequined Dolce & Gabbana gown).

5. Harvey Weinstein

Harvey WeinsteinCNN

No introductions are necessary for this American film producer.

On 5 October 2017, The New York Times ran a story accusing Mr Weinstein of three decades of sexually harassing actresses, production assistants, temps and other employees, and that he had ‘reached at least eight settlements with women’. Five days later, further allegations were reported in the New York Post. To date, more than 100 women have accused Mr Weinstein of sexual harassment, including 18 allegations of rape.

As a result, he was fired from The Weinstein Company’s board of directors, and several companies like Amazon and Apple have ended their collaborations with the film studio. The Academy of Motion Picture Arts and Sciences (AMPAS), the British Academy of Film and Television Arts (BAFTA) and the Producers Guild of America (PGA), among others, have all stripped Weinstein of his membership.

He is currently under investigation for his alleged crimes by the New York and Los Angeles police departments, as well as London’s Metropolitan Police Service.

6. William Bryant and Francis May

Bryant & May matchesMirror

A partnership between two Quakers, William Bryant and Francis May, in 1843 resulted in the establishment of Bryant and May, a British match factory. Their first order was for 15 cases of 720,000 matches and by 1860 their sales had risen to 27.9 million boxes. They were well on their way to success.

Behind the scenes, though, it was a completely different story. They employed mostly women and teenage girls who were forced to work 14-hour shifts, 6 days a week in horrendous working conditions for four shillings a week (which, in today’s money, equals about £76). Workers were also imposed with hefty fines for a long list of offences, including having dirty feet and going to the bathroom without permission.

But that’s not the worst of it: when the company switched from the safer red phosphorous it used to make matches to the cheaper white phosphorous, workers began developing a condition called phossy jaw. In layman’s terms, their jaws began to rot.

The entire ordeal led to the London matchgirls’ strike of 1888.

7. J Edgar Hoover

J Edgar HooverThe Daily Beast

If you dream of working for the FBI one day, be thankful you won’t have to work under J Edgar Hoover, the Bureau’s first director who was appointed to the position in 1935. And that’s because Hoover was, apparently, the very definition of a**hole. So much so that his employees were quite simply terrified of him and quaked at the very thought of his disapproval.

Horror stories about the man are aplenty. He would frequently fire agents who he thought ‘looked stupid like truck drivers’ or ‘pinheads’, relocated agents who displeased him to career-ending assignments and kept FBI employees on call 24 hours a day to help with menial tasks around the house – like fixing a lawnmower, for example. He also kept nude photos of EVERYONE, including former First Lady, Eleanor Roosevelt.

Fun fact: when Hoover once wrote ‘WATCH THE BORDERS’ on a memo, employees were too terrified to ask him what he meant, so they sent agents to patrol the Canadian and Mexican borders for a week. They later found out that he actually meant the page margins on the memo were too narrow for his liking.

8. Paula Deen

Paula DeenFood Network

Hailed as obesity’s guardian angel, celebrity chef Paula Deen is no stranger to controversy. And I’m not just talking about Cookbook for the Lunch-Box Set, a cookbook aimed at children which basically encouraged kids to eat cheesecake for breakfast and chocolate cake for lunch. Or how in 2013 she was targeted with a lawsuit alleging racial discrimination by former employee Lisa Jackson (the case was later dismissed because both Deen and Jackson are white).

In 2014, Deen found herself in the centre of another sh*t storm when she shut down her Uncle Bubba’s Seafood & Oyster House restaurant co-owned with her brother – without telling employees. Instead, she chose to post this little message on Facebook:

‘The closing is effective today, Thursday, April 3, 2014. Employees will be provided with severance based on position and tenure with the restaurant. All effort will be made to find employees comparable employment with other Savannah restaurant organi[s]ations.’

Basically, employees turned up to work on that day, only to collect their severance cheques in the restaurant's parking lot.

9. Ray and Faye Copeland

Ray and Faye CopelandWikipedia

Retirement can drive you to do some crazy things like buy a Lamborghini with your grandchildren’s uni fund or sell your house and travel the world. In Ray and Faye Copeland’s case, though, it drove them to murder.

Mr Copeland began a life of petty crime as a young man, stealing livestock and forging cheques until he was discovered and sentenced to prison for a year. Upon his release, he continued his little shenanigans, serving several others prison sentences, this time married to Mrs Copeland. When he was released again in the late 1980s, he resumed his criminal activities with a slightly altered plan: he would employ drifters and hobos who would buy cattle for him with his forged cheques and quickly sell it off. The farmhands, in the meantime, would disappear without a trace.

In 1989, a certain Mr Jack McCormick called the Crime Stoppers hotline to report that he had seen human bones while working on Mr Copeland’s farm and claimed that Mr Copeland tried to kill him. A total of five bodies were later discovered and it became clear that Copeland was getting rid of his employees to avoid paying them.

At the ages of 76 and 69 respectively, Ray and Faye Copeland were the oldest couple ever sentenced to death in the US.

10. Max Blanck and Isaac Harris

Max Blanck and Isaac HarrisFamous Trials

Max Blanck and Isaac Harris are, by far, the worst bosses in the history of bad bosses.

This dynamic duo were the owners of the Triangle Shirtwaist Factory, a women’s clothing manufacturer occupying the top 3 floors of 10-story Asch Building in Manhattan, New York City.

They employed about 500 people, mostly young immigrant women, who were forced to work 52 hours a week for $7–$12, the equivalent of $168–$289 (£124–£214). They also had a habit of locking doors to prevent theft by employees and unauthorised work breaks. On one fateful day, however – 25 March 1911, to be precise – a fire broke out on the eighth floor, quickly engulfing the building in flames, with workers still trapped inside.

Those who didn’t burn to death, either jumped or fell to their deaths from the burning building. A total of 146 people died, the youngest being 14-year-olds Kate Leone and Rosaria Maltese.

Have you ever had a bullying, tyrannical, micromanaging, sexist or otherwise bad boss? Join the conversation down below and share your thoughts and experiences with us!