'He showed up 45 minutes late, wearing shorts and Crocs': 20+ Bosses who got stuck with bizarre employees

Managers definitely play favorites with their employees. Some are pretty low-key about it, and try to treat people equally… but if you're buddy-buddy with them, they might let you do the easier types of shift tasks, or maybe they'll let you hang in the back office with them instead of interacting with customers. 

Other bosses show their favoritism far more blatantly. They'll shower their favorite employees with praise, let them take long breaks, and maybe even let them pick and choose their favorite tasks or shift hours. It pays to get along with the boss! 

These managers were in way over their heads with some employees, though. One discovered an employee was sneaking around in the ceiling, while another rolled their eyes as they saw a cashier ringing up their friend's meals for free. Check out a bunch of interesting stories below. 

Next, read about the employees who quit their brand new jobs as quickly as they could, like one person who headed to the door when their employer "asked if I was ok with a few days of 'unpaid training.'"

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Author image for Remy Millisky Remy Millisky
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  • 01
    Patamarick When I was a kid working at a grocery store, another cashier would often buy and then chug a half gallon of milk to get sick to go home. Job was horrid, so it was entertaining at the time.
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  • 02
    S plug 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 done. Finding reliable welders is difficult, so a lot of sh flies. This sometimes leads to weird employees. This one guy we hired stopped showing up. After like 3 days days, he walks in the door.
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  • 03
    He's bright red from being sunburnt to sh, 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.
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  • 04
    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.
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  • 05
    Splu... I was a Valet Captain at an expensive restaurant with the parking lot two blocks away and one of the valets I was supervising "took a wrong turn" in a customers 2016 Audi Rs7 and ended up getting pulled over & arrested for going 110 in a 70 on the interstate.
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  • 06
    [deleted] 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.
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  • 07
    So a few weeks go by and we just terminated him. I go back to the lunchroom one day, and 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".
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  • 08
    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
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  • 09
    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.
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  • 10
    Cheezburger Image 10513845504
    via Getty Images For Unsplash+

    The image does not depict the actual subjects of the story. Subjects are models.

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  • 11
    [deleted] Watched a cashier ring up his friend and pretty much give him everything for free. Nobody likes the store but don't make it so obvious.
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  • 12
    [deleted] SuperTarget deli. Had an employee eat food from the deli in the walk-in freezer which was the only place without cameras. He was shivering and holding an entire meatloaf, mouth full. I couldn't stop laughing.
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  • 13
    [deleted] I was a supervisor at a bulk food store. Had a staff member who was responsible for sweeping the floors. He would regularly snack on what he swept up.
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  • 14
    [dele... HR hired an employee to work on the mine I manage. He showed up 45 minutes late wearing shorts and crocs. I proceeded to fire him on the spot. Got a framed letter from corporate jokingly congratulating me for having the shortest tenured employee in company history.
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  • 15
    DetroitHero One time there was this guy who was a temp at this small, 30-man proto shop in Livonia. He ALWAYS wanted to be hired in full time. One day, he hatched a plan: He came in very early one morning and put up motivational signs all over the building. He made them himself out of cardboard and markers. The kind of
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  • 16
    thing you'd expect to see "will work for food" written on. The posters said things like, "If you're not giving 100% today, go home and I'll get someone who will," and, "What did you do to earn your check today?" He signed them all with the owner's name.
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  • 17
    Well, we hired him. It was hilarious! But as soon as he was full time, he started shirking and demanding raises. I guess he assumed he could join the UAW and get all kinds of benefits after he was hired. But we were just a small shop and didn't even have health insurance. He was fired about a week later and we were still finding hidden motivational posters for a month.
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  • 18
    beer... Not too crazy, but pretty stupid. I had a girl that worked for me at a Mortgage Company pull the credit report of her ex- boyfriend's new girlfriend (no idea how she got her social security number) and then went on the girl's
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  • 19
    Facebook page posting messages about all of her debt, and past due accounts, and the crappy kinds of car that she drives, etc. Got an angry call from the girl who ended up being a pain in my bot for a while.
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  • 20
    Edit: Forgot an interesting part - We fired the girl, and about a week later an agent from the department of Treasury comes in asking questions about the girl. Turns out, she was being investigated for a series of fraudulent things, including operating as a loan officer
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  • 21
    without a license, and taking out a bunch of federal student loans in her grandfather's name. He wanted information because in investigating learned that she had been fired from the company for some sort of malfeasance, and he wanted the details. She went to jail for a while eventually.
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  • 22
    [deleted] I had an employee call and tell me her mother død. Well, I got an anonymous phone call from someone telling me she was lying so I called the number I had on file to send my regards and I get an address to send flowers. In the meantime the office had collected an envelope of money to help. with the costs of the funeral and missing work. When I
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  • 23
    called, the mother answered and was shocked to find out her daughter used her death as an excuse to go to Vegas for the weekend. When she returned I help a big meeting with everyone in the office and presented her with the
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  • 24
    envelope of money and flowers, she took it and faked cried. I called her into my office to reveal that I knew and fired her and took the envelope back. She said she "don't give a f left. H II and
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  • 25
    [dele... I once fired a guy and he tried to go back to work. His crush was in the clock in room when I had to tell him to leave again. He cried on my shoulder as I walked him out of the building. Not because I fired him but because I told him to leave in front of his crush.
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  • 26
    mamadubba I have so many stories about this dude, me and my former boss interviewed him for a position in IT and i got a really weird vibe but my boss was really impressed by his cv (lots of stuff like "cisco certification course teacher") and I was about to quit so i didnt really put up a fight about it and he was hired.
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  • 27
    Day 2: He brought in a three feet long rc helicopter and put it in his office. Day 3: He was told to order a laptop for himself (part of the job was ordering it stuff) and bought the most expensive computer he could find, im talking titanium and a 10k$ price tag.
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  • 28
    Day 4: He ordered a office chair in leather with built in massage stuff. Day 5: BIG argument with my boss and he was told he couldn't do anything without me approving it first. Day 8: He told me he wanted to apply for public ip's for every single piece of equipment at all the company offices (several thousand ip's) because NAT
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  • 29
    sucked. Turns out he didnt know what it was (cisco. teacher remember) Day 9: He changed the domain admin password to a password some dudes at a irc channel had told him was the most secure password in the world. Around day 15: He told me he needed time off cause his girlfriend had left him for his rc heli instructor and he
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  • 30
    was scared she would take stuff from their apartment. There is so much more, he was fired a few weeks after i left. Last i heard he was selling vpn services to people using his own home broadband connection.
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  • 31
    icecreampopncereal Saw a dude fall asleep on a stand up forklift. How tired must you be to do that!?!?
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  • 32
    Cheezburger Image 10513845760
    via Getty Images For Unsplash+

    The image does not depict the actual subjects of the story. Subjects are models.

  • 33
    Yerok-The-Warrior As a Sergeant in the Army, my unit was out on a two- week field exercise. One of my soldiers decided to drink a dozen boxes of shelf- stable whole milk. He gets sick and has to go back to the rear.
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  • 34
    We find out later that he is quite lactose intolerant and knew it for years before going to the field. He bragged to some of his buddies about the scam and one of the other NCO's heard him. That started the investigation that got him demoted for malingering.
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  • 35
    [deleted] In the navy we had a broken accommodation ladder (it's a stairway attached to the ship for embarkation and debarkation that isn't always used if there is a brow on the pier) it was due for inspection and rather than fail the inspection the guys just unbolted it and let it fall overboard.
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  • 36
    5MinutesDesign This guy always tried to hide at work to avoid working. One day I was looking for him and I stepped into the bathroom. I notice a shoe print on the back of the toilet, and I look up and one of the ceiling tiles is pushed a little to the side. I climb up there, and this f the ceiling. is hiding in
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  • 37
    writermonk Heh. Back in the retail book industry in ages past I had this employee... He would take a 'bathroom break' anytime an employee got called into the office. Why? Well, because he had discovered (somehow) that if you went to the men's room and stood on the toilet
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  • 38
    and lifted one of the ceiling tiles, you could sort of make out conversations in the manager's office that was adjacent. He also discovered during one of his frequent smoke breaks that there was an access hallway for grounds maintenance (this was in a shopping mall of sorts) that also had a ladder that went to the roof. He'd occasionally vanish and
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  • 39
    basically go sit on the roof. If no one could find him, he couldn't get in trouble, he figured.
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  • 40
    B 501 MUST-DRINK COCKTAILS Acne Studion FREITAG MUJI 셀을받을하는 신경의 기술 GARM B PORTLAND SASA 도서대여 가능 1일권 1000원 7일권 3000원 GARM GARM B The Selfish Gene
    via YJ Lee on Unsplash+

    The image does not depict the actual subjects of the story. Subjects are models.

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  • 41
    VeryGoodGoodGood Company Hired a Contractor to take on some database development. The guy was hired as "Senior Database Engineer: Contract to hire". he was 53 (so hes had experience).
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  • 42
    he proceeded to do SO BAD on a project that we had to ask forgiveness from a client, refund all their support hours, and have our JUNIOR developer (who was later promoted due to good work) redo the contractor's 2 month project. It took the Junior dev 1 week (35 hours).
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  • 43
    kitch... I was a kitchen manager, and one night I was out on our back dock, and saw that someone had left a full trashcan sitting out beside the dumpster. I went over and started to lift the trashcan to dump it in the dumpster, when the back door opened, and one of my cooks walked out. He immediately rushed over, insisting that I not dump the
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  • 44
    trash, and let him do it, because, "It's too heavy for you! I don't want to see you get hurt. Let me do it." Now, I am a small female, but I'm tough, and I've been lifting heavy trashcans for years, while the guys looked on and never batted an eye, so I thought that was strange, but, whatever. I just kind of put it in the back of my mind.
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  • 45
    A couple of hours later, we were closed, and my employeees were all leaving for the night, while I was in the office doing the deposit and finishing up all of the end of day stuff. The same cook from before, poked his head in the office to say good night, then, instead of heading out through the front, like everyone else had done, proceeded to head out the back door, through a dark kitchen, where all the
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  • 46
    lights had already been shut off. I thought that was strange, too, so I turned to the monitor which showed all of the cameras that we had throughout the restaurant, and pulled up the camera for the back dock. Sure enough, the cook exited through the back door, then went behind the dumpster, out of camera range, retrieved a duffel bag that was stashed back there,
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  • 47
    and left. From there, I pulled up the footage from the trashcan incident from earlier, and could see that as soon as I went back inside, the cook looked around, then dug through the trash, and pulled out something that he had buried, and took it back behind the dumpster. By pulling up footage from different cameras, I was able to see that earlier in the night, he had taken the trash
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  • 48
    can into the walk in freezer, where there are no cameras, then exit with the same trash can a few minutes later, and push it out the back door, where I came out and saw it, about 10 minutes later. It all made sense now. So, I burned a copy of all footage that I had found, in sequence, and left a copy of the dvd for my general manager, who was opening in the morning, with a note
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  • 49
    that read, "Watch this. I think I just solved our food cost problem." Well, the gm watched the dvd, then called the cook into the office, had him watch the dvd, then asked him to sign his termination notice. The cooks defense was, that I had set him up.
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  • 50
    He said that he had dropped some steaks on the floor, and they weren't able to be used, so he asked me if he could take them home, and I said, yes. Then, I decided to set him up for stealing, because I'm a bi 1. I like to imagine that the conversation went something like this. Him: Hey, can I take these unusable steaks home?
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  • 51
    Me: You most certainly can. But, only if you bury them in trash and store them in your duffel bag behind the dumpster for a couple of hours in the sweltering heat of mid-August. Him: Sounds reasonable.
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