People Are Sharing The Wildest, Most Messed Up Thing Their CEO/Boss Ever Did

Warning: This post mentions sexual harassment and substance abuse.

Workplace dynamics are strange, especially as they relate to dealing with upper management, bosses, or CEOs. It gets especially tricky to navigate when the power imbalance feels like it’s being abused.

But when that imbalance gets exposed? That’s when chaos is unleashed. Look no further than the incident with Andy Byron, the former CEO of Astronomer, who got caught in 4K cozied up with a colleague while married at a Coldplay concert. He was forced to resign, but the fact that he was that close with someone he worked with suggests that the workplace dynamic was probably a little sketch.

A crowd at a Phillies game is shown on the big screen holding a humorous sign about not cheating on their significant others

Isaiah Vazquez / Getty Images

However, that’s really the tip of the iceberg when it comes to workplace scandals. I recently asked members of BuzzFeed Community to chime in with the absolute worst things their bosses or CEOs have ever done. I won’t lie, some of these made my jaw drop in real-time:

Note: These responses have been edited and condensed for clarity. 

1.“The company CEO called a meeting of all home office staff (mid-December) to announce no annual Christmas bonus this year, the end of the three company autos for employees who were required to always be on the road, and a wage freeze for at least the next 12 months. This was all supposedly due to ‘cash flow’ issues in a weak market. Three days later, he showed up with his brand new, company-provided high-end Mercedes sedan. And yes, he almost never left the home office for work.”

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2.“Asked to see photos of my breasts before and after breast reduction surgery because ‘they’re still massive.’ That might not be the most inappropriate thing she did because she did a lot of horrible things, but it sure sticks out in my mind.”

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3.“I worked overnights at a small retail store with a skeleton crew. No managers until the morning shift rolled in. One night, one of my coworkers came in when it was just she and I on shift and said she was in the middle of a miscarriage (very, very early stage, but I digress). I asked her what the hell she was doing there and if she had called our direct manager to tell him she was in a medical emergency. She said she did, but he didn’t want to come in to cover for her. His defense? ‘I thought she said she ate BAD CARROTS.’ We flooded HR with complaints, and I left shortly after, so I don’t know what happened to him. Bad Carrots. Burn in hell, Brian.”

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4.“My Boss took me to a company event. One of the managers took the stage and sang a popular song at the time. ‘Take This Job and Shove It.’ It was a joke, but he was terminated the next day.”

Office holiday party with people in Santa hats. One person joyfully spins in a chair while others cheer and celebrate around them

Aleksandargeorgiev / Getty Images

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5.“The CEO, a 50+-year-old woman (it matters to the story), whom we’ll call ‘M’, and her then-partner and co-CEO, a 30-ish-yeah-old woman (again, important to the story), whom we’ll call ‘C’, wanted to have a child together.”

“It was decided that C, being younger, would be the carrier, and they would use donated sperm. Unfortunately, C couldn’t carry the child. So it was decided that M, who’d successfully carried a pregnancy in the past, would be the carrier utilizing C’s egg. For the donation, they used M’s grown son (we’ll call him G). It worked — twin boys! So, M is both mother and grandmother. G is both dad and half-brother. Boggles the mind. Always interesting when that story comes out to new people. It wasn’t a secret at all.”

—Anonymous, 55, Canada

6.“My boss at a well-known supermarket got in a fight with his wife in his office, which was located in the front of the store that didn’t have a roof, just four walls, and then the store roof, so there was about 3-5 feet of open air. We could hear everything, and the wife was yelling at my boss because she’d just found out he was sleeping with their son’s girlfriend! My boss married his son’s girlfriend and divorced her, too. The wildest thing was, she also worked at the supermarket!”

Man lying in bed smiling at phone, while woman in background appears frustrated or puzzled

Peopleimages / Getty Images

—Anonymous, 54, California

7.“CEO tried to run the boss over with his car.”

—Anonymous, 25, Australia

8.“The (married, 60-something) CEO of a company I used to work for slept with any woman willing and able on the regular, but the final nail was after a prolonged affair with a young woman who was a key department lead. They fired HER and kept him, and the company hasn’t been the same ever since, but that’s just the lead in: fast forward several years later, he divorced that previous wife and married a long-term other non-employee fling.”

A hand holding a pen is poised over a "Petition for Divorce" form, with a wedding ring placed on the paper

Labsas / Getty Images

“There was a transfer of power coming as he was set to retire and mentor the incoming CEO for a couple of years. He died unexpectedly in his sleep. Healthy man, no serious addictions, etc. Well, years later, it finally came out that he and the new affair wife were quietly on the rocks (because he was having another affair). He had filed for divorce, and that disgruntled wife refused an autopsy despite his children’s wishes. Turns out she was having another affair with the incoming CEO, and the outgoing CEO’s death occurred three days prior to a divorce moratorium on the prenup, where she ended up cashing in for north of $300 million. If he had made it three more days, the divorce would have been finalized, and she would’ve gotten nothing, and it would have all gone to his kids instead of her getting a third of his estate. You can’t make this stuff up!”

—Anonymous, 50, Alabama (but this happened when I lived in Oregon)

9.“She was running an umbrella company that she and her husband owned, consisting of at least nine micro businesses all based within one town in the UK. She and her husband own some of the biggest food brands in the country and are in the top 4% of wealth in the UK. They are filthy rich, collect super cars and have houses all over the world, along with a vineyard, an extensive lettings portfolio, and two castles.”

Person in an office rubbing eyes while holding papers, sitting at a desk with a laptop and open notebook, appearing tired or stressed

Moon Safari / Getty Images

“It transpired shortly after starting to work for her that the company was completely and utterly bankrupt, and was scraping by each month by hopelessly moving money around illegally between each business. We regularly had suppliers who would physically come into our stores and remove their stock from our shelves in full view of customers because we owed so much money to them, and we were told by the CEO to deny that we were in the wrong. Instead of telling companies we couldn’t pay, she ignored their final demands and legal letters, and even forced one small business to fold because she owed them so much money. We had the bailiffs arrive several times during my time there, and were told to lock the door and stay quiet. We all held our breath come pay day as it was always somebody’s turn to not be paid because the funds had run out, and it was a regular occurrence for the utilities to be shut off due to unpaid bills, so in the winter we all wore thick padded coats in the office at our desks, which she used to get cross about and shout at us for as it didn’t look professional. She was in complete and utter denial that we were on a rapidly sinking ship.The final straw for me was finding out that my pension was being paid late to my pension provider, MONTHS at a time late, with some payments not making it to my pension account for up to six months after they were due, despite showing on my payslip as having been automatically deducted. Long story short, HR confronted her about it, and she verbally admitted she was using the monthly company pension pot to pay off as much outstanding debt as she could, and hoped nobody would notice. This led to nine of us resigning at pretty much the same time and walking out as fast as we could. As far as we know, she’s being investigated, and is still denying any wrongdoing, and of course, is still trying to keep the sinking ship afloat, living in denial that anything is wrong. “

—Anonymous, 33, UK

10.“One of the directors of the company had a little boy crush on one of the graduates working there. The grad sat at the desk next to mine, and the director was talking to him, standing right behind my chair. They were talking about the grad’s sex life (very appropriate for the office) and how he ‘probably gets all the ladies’ while the grad plays the humble card. The director is always gassing the grad up and living through him (because his youth is over — he’s married with three young daughters) and hired him only because he was ‘charming’ (his words, not mine) in his interview.”

“Anyway, the director (remember, standing RIGHT behind me, practically breathing down my neck) says to him, ‘Come on man, even *my name* would get on her knees for you'(!!!). The grad was practically speechless, and I just pretended I didn’t hear it and kept typing. The grad was like ‘Bro, no, that’s messed up,’ and the director laughed it off. It was like I wasn’t even there, and made me think if this is what they talk about when I’m there, imagine what they are saying when I’m not. When I quit the job (a few months later), I told HR, and she was horrified. Wish I had reported it sooner, but I was scared. But making jokes about a female grad giving head to a male grad when she’s RIGHT THERE is so f*cked. I had a boyfriend, and they all knew that. Maybe that was the joke. Either way, I wonder how the director would feel about his three daughters being talked about like that in the workplace.”

—Anonymous

11.“I used to work at a Kmart. That should tell you something. General manager was always kind of off.”

Storefront of a Kmart with large "Kmart" sign above entrance. People are entering beneath the canopy. Vending machines are visible on the left

Colin Mcconnell / Getty Images

“One day, another coworker had to escort her out of the store. She was stumbling all over the place and was slurring her words. Her mouth and lips were also stained blue because she was going to TOWN on these blue raspberry sucking candies. Come to find out, she had a major pill problem. Unclear what exactly it was, but the pharmacist basically violated HIPAA laws to gossip to anyone who would listen that she refilled her prescription multiple times a week and was clearly abusing it. She also got in trouble for paying for her daughter’s wedding dress using the company credit card. She was let go shortly after, and I think she cleans houses now.”

—Anonymous, 31, Iowa

12.“I used to work at this burger spot during COVID. The owner was a huge ladies’ man, always checking out the clientele and trying to sleep with every girl who worked on the block at various other businesses. During my time there, he started dating a ballerina who had no current work due to the pandemic and made her his manager of said burger spot. Here’s where it gets wild…I was continuously asked to make sure she wasn’t around or take her out of the neighborhood so he could continue to hit on other women in the area.”

A person opens a door slightly, revealing a couple embracing in bed, wrapped in a sheet

Toshimself / Getty Images

“The funny thing was she lived ABOVE the burger joint, hence how they met. One night, I took her out, and she got really drunk and upset. She basically told me she knew what he was up to and saw what went down in the restaurant cameras when she was tucked away in the office. She demanded we head back to the block where the burger place was to hang out at neighboring bars. We passed the shop, waved at the cooks, and the next thing I know, I’m getting hounded by the owner who saw us on the exterior camera — he was furious I brought her back to the block that SHE LIVES ON. I was fired the next day. This guy had a side piece down the street at a tattoo shop, a server in the club across the street, and two more prospects who worked in bars on THIS ONE BLOCK. Never in my life was I that happy to be fired from a job. A year later, she had to contact me to send me my tax forms, meaning that she was probably still with this douche. Poor girl. “

—Anonymous, 38, New York

13.“At a business lunch meeting with a vendor, the CEO, CFO, and Operations Manager of my company were discussing replacing our building’s HVAC RTUs (this was gonna be a massive and expensive project). The vendor, with whom I have developed a great working relationship and friendship, who also happens to be incredibly attractive, brings up his upcoming destination wedding and invites the CEO. I tell our vendor that my son and I will be there. The CEO, in front of everyone, says to me, ‘Why the f*** do you want to go? What are you gonna do? Wait for the ‘speak now or forever hold your peace’ line and get up to profess your love for him?!'”

“CEO, CFO and OM are laughing their butts off, I’m awkwardly laughing, and the vendor turns beet red and changes the subject to something completely unrelated. After the meeting, he called me to apologize for my own boss’s behavior, and told me he was red in the face because he was pissed that the CEO said that to humiliate me.

We’re still friends to this day. I, however, was not invited to the wedding. I started looking for a new job after that…and the vendor was one of my references. He even recommended my name to a few of his other clients. I ended up leaving a few months after that.”

—Anonymous, 39, TX

14.“I work at a commercial real estate company, and there have been some wild times in that office. Brokers doing coke at night in their offices, racking up over $6,000 on the company card at the strip club, and at one Christmas party, drinking a fish (like in The Wolf of Wall Street). One broker is hooking up with his ‘brokerage coordinator.’ He’s married with kids, but continues to hook up with her. He’s bought her breast implants, given her undeserved promotions, paid her rent, you name it. The entire office knows, and nothing has been done. “

Leonardo DiCaprio as Jordan Belfort in the Wolf Of Wall Street

Paramount Pictures

—Anonymous, 35, Denver, CO

15.“I once overheard the floor manager tell someone that he ‘doesn’t know what to do if he ever has to fire them…’ and it turned out that he had been working his way through most of the women on the floor. There were only three of us who knew for a fact he hadn’t slept with.”

“Guess he was bored after his previous side piece got fired for wearing mini skirts with nothing underneath and leaving ass prints on desks (she liked to sit on the desk when talking to someone). “

—Anonymous, 39, Arizona

16.“In a management meeting, my team’s boss told us how important it was to have a work/life balance and take time for ourselves outside of work to avoid burnout. Then, immediately said that we should all have our work phones with us at all times and be available at all times. Someone asked her to clarify, as those two sentences seemed mutually exclusive. She repeated the two sentences, word for word, which was her clarification. This was the kind of job where we were saving PDFs, not babies, BTW. “

Man in a suit appears stressed, talking on a phone while sitting at a desk with a laptop

Djelics / Getty Images

—Anonymous, 40s, Midwest

17.“A few things from the same boss. When I was 16, I worked in a kitchen at a pub. The owner was a heavy drinker, so on a busy Friday night, he came up to me and demanded that I clean the oven that the chef was using. I told him, ‘Uhhh, chef is using it, it is currently on, and extremely hot. You sure you want me to clean it right now?’ He yelled back at me, ‘Of course I f***ing do! I wouldn’t ask you to do it otherwise. Now f***ing clean it now!'”

Car flipped on its side against a building at night; emergency personnel on scene

Picture Alliance / Getty Images

“The chef came up to me after he heard that and told me to ignore it. The second thing he did was a few weeks later. It was a Sunday morning, and the pub opened at 10 a.m. to get the brunch crowd. We were all there at 7 a.m. to get everything ready. The issue: he was nowhere to be found, and he was the only one with keys to get in (he was controlling AF). At 8:30, he finally showed up, drunk, driving his car, jumping the curb, and crashing into the patio. Needless to say, all the staff ended up quitting.”

—Anonymous

18.And fianlly, “Boss cheated multiple times on his wife of 25 years and expensed the company for meals and a hotel room. Presented himself as a pious, family man.”

—Anonymous

What’s the wildest thing your boss has ever gotten away with? Share your story in the comments.

If you or someone you know has experienced sexual assault, you can call the National Sexual Assault Hotline at 1-800-656-HOPE, which routes the caller to their nearest sexual assault service provider. You can also search for your local center here

If you or someone you know is struggling with substance abuse, you can call SAMHSA’s National Helpline at 1-800-662-HELP (4357) and find more resources here.

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