Reddit Confessions: 15 Bosses Tell All About Their Craziest Employees

But what most people don’t realize is that bosses have their own set of similar stories from their perspective; these are the times bosses hire people to work under them and they turned out to be totally crazy. Thankfully for us, that was the topic of discussion on a recent AskReddit thread, and people had some pretty insane stories about being the boss.

I went through the long (very long) thread and found the top 15 craziest stories bosses or former bosses told about their loco employees. And trust me, they have A LOT to say. 

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15 The Great Muffin Crime Lord

Redditor dawnieduh shared her story of an employee who orchestrated a ridiculous muffin crime ring:

"Two things, same store: I used to be a manager of a high volume Starbucks inside of Target and I had hired this 18-year-old girl who was VERY perky and energetic, so I thought she'd be a great fit. She went through training with no problem, was one of my top baristas and helped me a lot with general keeping of the store. About three months in, though, her crazy started coming out. She was diabetic and would intentionally leave her insulin home just so she'd have a dramatic episode at the store. She'd start crying in the middle of her shift to get attention from customers, and there was one time that she wanted to go home early but there was no one to cover for her so she made herself throw up in the sink in the back room!! Because the other two things were sensitive subjects (I can't write someone up for being diabetic or dealing with mental illness if that's what she was dealing with), I couldn't do a whole lot about her. That was until...

One day, I came to work, and my Loss Prevention Team for Target was escorting one of my other employees out of the building. I was confused and wondered what the hell was happening, but they weren't able to disclose anything at the time. Later that day, the crazy girl also gets escorted out. Still, nothing was said to me. As the days went on, I saw every single one of my employees get escorted out with the exception of two (who were also later fired). Turns out, crazy girl had put together this big operation of stealing pastries and sandwiches from the store and writing them off at the end of the night. Because Target differs from Starbucks, we didn't have a solid way of monitoring that kind of thing because it gets thrown in the garbage at closing instead of counted and donated. So, I lost 8/8 of my employees in under one week because of pastry theft. I wasn't told anything about it at first because they were investigating me as well and they didn't want to disclose in case I was also guilty."

14 Castaway Employee

shitterplug describes an employee that apparently would go to the ends of the earth to get into work:

"I manage a small weld shop. Generally, I don't care about less than clean background checks or pot, as long as you come into work every day and get sh*t done. Finding reliable welders is difficult, so a lot of sh*t flies. This sometimes leads to weird employees. This one guy we hired stopped showing up. After, like, three days, he walks in the door. He's bright red from being sunburnt to sh*t, and his clothes are torn to shreds. Dude was drinking on a little aluminum boat and somehow got lost at sea. He looked like Tom Hanks from Castaway! He didn't have cell phone reception, so he wasn't able to call me. He did take a bunch of pictures over the few days he was lost at sea, though. Including one where he was being rescued by the coast guard. I gave him the rest of the week off. Cost guard took him to the hospital, he checked himself out, and immediately came into work. Didn't even go home and shower. Odd dude."

13 Future Walt White?

Trailblazed83 had an amazing story of what sounds like a super fun dude to work with, but still, pretty nuts:

"Well, I'm not a boss anymore, but I got a story. I worked at a Wing Zone in college, managed for a little while. I had a sport high energy kid working as cook one night, he was into science experiment-type pranks. One night when I wasn't paying attention to him and focused on orders going out, he got caught up on his cooking and wanted to eat dinner. He went next door to Publix and bought something to eat along with some dry ice they keep stored by the freezer section.

He had talked up making a dry ice bomb earlier, which I figured he would do outside. But once he got back, he disappeared. He and a driver ran out front and grabbed me on the way out. Once we got out of the store there was the loudest sound I've heard, like a shotgun blast or firecracker shot at close range and all the doors in the store and walk in cooler flew open for a second when the blast hit.

We go back in and walk into the cooler. Nothing seemed any different though and the dry ice bomb was gone. Finally someone looks up and behold; a 20 oz bottle stuck straight into the stainless steel ceiling of the cooler, the kid had to hang his weight on it to pull it out. I can't say I was mad because no one or thing was hurt, and it's not my store. I was impressed and encouraged the scientific spirit, just next time, do it outside. It's people like that kid that make life kind of fun. I hope he became a bad a** science teacher."

12 For A Bad Time, Call...

rottenbanana127 was done SERIOUSLY dirty by a now-ex employee:

"I was a manager of a couple departments for a local grocery chain a few years ago. I had a girl on one of my teams who was terminated for basically breaking every rule in the book — she sucked.

Even though I wasn't the one who fired her, or made the decision (I didn't have that power), she decided to take revenge on me.

A week after her termination I started getting calls on my cellphone from strange men wanting to have sex. It turns out she made a fake listing on Craigslist, soliciting me for sex (I'm a woman). After much digging and convincing one of the strange dudes to assist me with getting evidence, I was able to make a police report. It's a two-year felony to impersonate someone online/solicit them without permission (in Michigan, at that time).

The fun part is when the police wouldn't press charges because it was a one-time thing. Yep. This girl endangered me by OFFERING ME FOR SEX ON CRAIGSLIST WITH MY PERSONAL CELLPHONE NUMBER but it was a one-time thing. I'm still pissed."

11 Double Trouble

-jackschitt- had not one, but two stories of insane employee shenanigans, however, the one below takes the cake:

"The first person we hired appeared to be a godsend. She was very comfortable around computers, and by day two already was well on her way to having her own routine for the day mapped out. She was picking up on her job far, far faster than anyone in recent memory.

Then her boyfriend calls the school she was assigned to. "Who the f*ck is <manager's name>?! Why the f*ck is his name in my woman's phone? Don't give me that bullsh*t that she's not available! Put her on the f*cking phone now or I'll go down there and drag her a** out!" This caused the lockdown of the school, for obvious reasons.

She was called into the admin building and asked to give information on her boyfriend, since authorities were interested in pressing charges. Her response? Totally nonchalant: "Oh, don't mind him....he gets like that from time to time. Just don't press charges, please.....if he violates his parole again, he'll be back in jail!" She was immediately fired. I Don't know if they ended up pressing charges against the boyfriend."

10 Mystery Man

Caseyoc brings us a pretty inexplicable action taken by an ex-employee in the Forest Service:

"I used to supervise a Forest Service recreation crew. One of my first season crew members was starting to show himself as a bit of a screw-up, and one Monday one of my other crew members came in and said, 'What happened to X's truck?'

We went down to our garage and there is the truck and it looks like someone has taken a baseball bat to it on the passenger side, and the hood, cab, and top of the tailgate. The driver's side is fine. The kid had gone out to do his work, some crazy sh*t happened, and then rather than reporting it to me, he just parked the truck and went home.

My boss and I talked about it and we decided the kid would get fired when he came back to work on Wednesday (which was my day off). When I came back to work, X was gone and I asked my boss, 'How'd the truck get wrecked?' He said, 'I never asked him.' To this day, I still have no idea and it drives me a little crazy."

9 Adventures With Knives

Bmoviescreamqueen has a story that will really make you just go, "what in the actual hell?". It just goes to show you, pretty much anyone can turn out to be a total psycho.

"I was training at a gas station. First hour was the normal rush, and everything went normally. When the crowd died down, we started to settle in and I started going through the normal routine with him. As we're talking, he pulls out a knife that's several inches over the legal limit and a stone, and starts sharpening the knife. I immediately say 'You need to put that back in your car now and never bring it to work with you again. Carrying a concealed and illegal weapon is grounds for immediate termination if security or management sees that.'

His response: 'Oh, Ok.' He starts walking to his car, presumably to drop the knife off. And then he drives away, never to be seen again."

8 It's Her Sh*t In A Box

Allworknoplaytoday tells us about a seriously disgruntled employee who decided to get a little creative with expressing her displeasure:

"Worked at a new Fry's that opened in my old town a number of years back. It was pretty bad initially and they REALLY overworked employees. The turnover was huge and later a suit was filed against this specific Fry's. In any case, when I started, there was a blonde woman who I forget her name now, let's call her Beth. Beth was overly enthusiastic— to the point of being incredibly annoying to any and every employee/customer. Beth was apparently also a pathological liar and frequently left her shifts early to do god knows what...

When she was fired, she came back with a nice, purple present. All wrapped up with a white bow and everything. It was meant to be an apology to the manager, but she quickly dropped it off and took off saying she was busy. It smelled like it had been doused in a gallon of perfume, but she seemed half crazed so whatever. The manager for her department at the time took it and opened it near the registers. And inside was a lump of sh*t. She sh*t in a box and gave it to her manager. As a gift of course..."

7 Shady AF

Yash_the_stampede describes an employee who was nowhere near as slick as he thought he was:

"I work as a supervisor in a drug store. One night one of my employees was seen just letting someone walk out with hundreds of dollars of merchandise. A few minutes later he went outside to collect the shopping carts. I'm reviewing the video evidence of this happening at the time, and on the phone with my store manager.

The employee was outside for a pretty decent amount of time. I hadn't noticed right away because I was busy collecting the evidence, but my other cashier called me up and told me that he still hadn't come back in, 15 minutes later. As I walk downstairs, he comes back inside with one shopping cart and the guy was high as a kite. Because I am not a store manager, my hands are rather tied as far as what I am able to do at the time, so I just send him home and keep someone else for the rest of the night.

The employee called me later (I happened to be best friends with his sister) and he started talking about how he hates snitches and that people should just leave other people alone. He was rambling on and on. The next day the Loss Prevention Manager was there, as well as my manager. The employee was terminated. It turned out that he would let his friends walk out with baskets of merchandise without scanning it. Then, he would go collect carts and they would give him meth in payment for all the stuff.

He thought he had this master plan, and that he was sticking it to the man. It was really sad to see. Since then, the employee has been incarcerated and successfully completed rehab. I am glad to say that he is doing so much better now, and has apologized profusely about the entire incident."

6 Do NOT Mess With Cats, Dude

Jeannieb's story made me absolutely furious. What is wrong with people?!

"We own a salvage yard (junk yard) and we usually have a few cats around. Every now and then one of these cats will claim us and live in the office. We feed it, take it to the vet, and it becomes our junk yard pet cat. One particular cat was awesome and all the guys loved this cat, even the burly guys. They would all share their lunches with the cat.

This one guy that used to work for us was a real a**hole. One day he decided that he didn't like the cat anymore. He took a can of spray paint and painted the poor kitty. All over, head to tail. When the cat came into the office, my husband, who is the boss, went ballistic.

The first thing my husband did was wash the cat off as best as he could. Then he went into the shop and raised holy hell. Screaming at everyone until a new guy finally told him that he saw Jim spray paint the cat. My husband was raging and wanted to really f*ck this guy up bad, but instead, called the cops and filed animal cruelty charges and fired him on the spot.

This guy had the balls to file for unemployment for unlawful termination. He was denied several times but kept opposing the judgement. We fought his argument all the way to the highest level of State review, where he was granted full unemployment benefits. The reason was, even though he broke the law while at work, it doesn't (didn't) state in our handbook "no spray painting of cats" or "no unlawful activities at the work place." We thought that would have been a given."

5 Cubby Craziness

Retrostretch's story involved an, uh, unusual space arrangement made by an employee:

"I was a supervisor for a 'high end' retail store that we were preparing for Grand Opening. We had hired one guy (we'll call him 'Tom') that was in his early to mid twenties. Over the course of a couple weeks I noticed that I barely ever saw 'Tom' during his shifts after I sent him off to do something. One day I sent him onto the sales floor with a cart of merchandise to stock, and realized that it had been over 20 minutes and all of the other employees had already been back two to three times. I was the only manager on so I knew he didn't get sent to do another task, so I asked if anyone had seen him. One girl turned to me and said 'He's probably in his cubby.' And then proceeded to show me where it was.

Apparently 'Tom' had created a cubby for himself about three-four ft wide behind some old shelving units. He had stolen a heated blanket, pillow, and various food items off of the sales floor and that's where he had been hanging out for the majority of his shifts for over a month. Checking in with various managers at 30-45 minute intervals so as to be seen by someone.

This was his 3rd or 4th offense so we fired him. He proceeded to rip his shirt in half and start crying while screaming 'WHY!?' over and over again at the top of his lungs. We then escorted him out of the building, where he continued screaming and crying while beating his chest and hawking loogies on our windows. This kid was a complete tool. He harassed all of the girls relentlessly (even me — his supervisor), tried to sell drugs on the premises and stole non stop. I don't know why he seriously didn't understand why he was being fired."

4 That's A Little Much

Remembername had an employee that went a little bit overboard on his off time:

"I worked for a big company years ago as the shipping manager. One of the guys I hired was an ex-Russian army guy. He was pretty good, hard worker, and all that. Still a little off, if you know what I mean. So one day he doesn't show up and no phone call. The next day he calls me and he sounds like he's high. He's in the hospital. After work I go by the hospital (we were kinda friends) and his whole right side is fu*king black as night. Not a stitch of white. Serious bruising. Broken leg and arm.

I asked him what the hell happened and he told me that, him and his friends were 'having a party' in his fifth floor apartment. He was having an argument with one of his friends (as seemed to be a regular Russian thing for them to do). His friend was saying that he never follows through or something like that. So my friend stated that he always follows through. My friend says 'If I told you I would jump out that window, I would.' His friend says,. 'Hahaha, you wouldn't dare.' So, crazy f*cking Yuri runs and leaps out the window, down on to the parking lot below. He spent over a month in the Hospital to prove a point. Fu*king ridiculous. He quit and I didn't see or hear from him until a year later he called me on the phone all drunk telling me I was Jesus. The end."

3 Come On, Dude...

ASimAteMyBaby had one employee who just didn't get the hint:

"Was cashier manager at big box store. There was a useless kid that finally stopped showing up. A few days go by, and I see him walk in, so I assume he's going to come up front and we can do the whole formal exit process since he missed shifts. He never comes up front, nobody has heard from him.

So a few weeks go by and we just terminated him. I go back to the lunchroom one day, and the useless kid is sitting there. I ask what he's doing and he says he's on break. I'm like 'lol no, you stopped showing up weeks ago and were terminated.' He leaves to go 'back to work.' I confirmed with all managers he was fired, not working in another part of the store. He shows up in the lunchroom again a few weeks later.

Turned out he didn't want to tell his mom he doesn't want to work. He kept letting her drop him off, he'd hang in the lunchroom for a bit because his mom apparently is friendly with another employee, so this way it looks like he still has the job to his mom."

2 The Man Of Many Faces

Weedmoneylol’s story is actually pretty funny, and definitely shows us that people will do pretty much anything to keep themselves entertained. Now that I think about it, if I worked in a call center, I would probably do something similar, in all honesty.

“I was doing a weekly call monitor on one of my better employees and found he was doing an Indian accent. I was a bit surprised, so I went back and listened to 5+ calls of his from that week and found he was doing different impressions for almost every call. Arnold Schwarzenegger, Mickey Mouse, Apu from The Simpsons, a pretty solid Christopher Walken, and a few others.”

Think about it. The job involves just making these long conversations happen over and over again, for hours at a time, day in and day out. Wouldn’t you want to spice it up a little? Also, it would be hilarious to get a cold call from someone doing a Mickey Mouse accent.

1 God Damn It, Bob

InspectorVII tells us all about Bob, who had ONE JOB TO DO:

"During orientation, he challenged me on several of our rules, many of them having to do with Health and Safety. He did not want to wear eye protection, or closed toed shoes since it was 'too hot' in our climate controlled manufacturing plant. He wore a bluetooth headset which he proceeded to answer several times through orientation and when informed that personal cellphones use was only permitted during scheduled breaks, he informed me that he was conducting 'business' and needed it.

Bob was untrainable. He had one job to do, balance material in a centrifuge and make sure it was draining. We had charts posted outlining how many of what to put in, and how to arrange things.

So after working with him one day, showing him and overseeing him arrange and balance, I was satisfied that I could leave him unattended for five minutes while I grabbed a washroom break. I was dead wrong. I start to hear the clanking of metal on metal and run back to shut down the machine to find that it was not loaded or balanced properly. When asked why he loaded it against regulation he said, 'It takes too long to arrange everything.' Still nobody wants to get rid of him except me. So, as the GM of a manufacturing plant, I spent the next week with BOB, babysitting him as he loaded a centrifuge until I finally had to leave him to do my actual job. In under a half hour, from improper loading he had damaged the machine. While I was loading setting up the back up, I instructed him to go to the board room to review the loading charts and that I would call him back when I was finished.

About 20 minutes later, I go to the board room — no Bob. There is nobody in the mens room. As I am walking back to my production floor, I notice that there is somebody in the presidents office. This is pretty strange since the president was out of the office that day and the only two people who are permitted in the office are myself and the office manager. Wouldn't you know it, just down the hall, the office manager is happily chugging away at some reports in her office. So I go in, only to reveal Bob watching some of the most depraved Spanish porn on the presidents computer."

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