vote for the worst boss of 2019

It’s time to vote on the worst boss of the year!

We’ll crown the worst boss of the year later this week, based on your votes … so please vote below. (Voting ends at 11:59 p.m. EST Wednesday night.)

{ 376 comments… read them below }

    1. Pilcrow*

      Yeah, that’s what I thought! I may have said it was “an embarrassment of riches” except… there’s nothing good here. An embarrassment of embarrassment, maybe?

    2. Hills to Die on*

      ‘You’ve all made a spectacular showing in 2019 and even though I can only vote for one of you, I want you to know you’re all losers in my book!”

    3. Nanobots*

      every single one of these bosses needs to never had contact with the human race again. They need to be blanked out like that episode of Black Mirror.

    4. MusicWithRocksInIt*

      I mean, these are all awful, but I feel like 2018 was a touch worse? I feel like this stuff calls for more of a bracket than a straight up vote…

      1. Anonymous from Seattle*

        Wow, no way to vote for the boss that laid me off because they thought I was incompetent when I had an ongoing health condition that worsened my mental health condition? Thanks Deloitte.

    5. AFRS*

      Exactly! I went with one that combined a health issue, sexism, and horrifically gross cluelessness. But all of them were so so bad.

  1. Amber Rose*

    It was less difficult to choose this year. Sadly not because the options are less horrible, but more just because one of them stands out as extra horrible. :(

    1. RC Rascal*

      A Rogue’s Gallery, as usual. I wonder if any of these horrible bosses has ever read about their nominations??

      1. Sarah*

        The type of people that do things like this have never once second-guessed their management or had the self-awareness to seek advice from someone else.

    2. KayDeeAye*

      This is the first year I haven’t felt torn. I mean, don’t get me wrong, there are some extraordinarily bad bosses here, but the anti-mastectomy boss is the winner by a mile. It would be very hard to pick a single runner-up, though!

    3. Mazzy*

      I thought the opposite. Nothing is sticking out, they’re all bad. The mastectomy one sounds the worst but it was a one time thing and coworkers were gossiping, so it wasn’t purely a bad manager story. That’s why I picked the daily therapy one because it’s invasive and insulting and also tedious and ongoing and crushes their souls over a longer period of time.

        1. valentine*

          The mastectomy one is the worst because of the tripling down and shunning in the update.

          Compared to that, pee boss is a number 2.

        2. polkadotbird*

          I just read the update and was flabbergasted about how worse that got. My heart breaks for the OP.

      1. Princess Consuela Banana Hammock*

        Oh, the mastectomy one is really really bad, Mazzy. It helps to read the update, where it went from bizarrely unkind to outright hostile.

      2. blaise zamboni*

        I felt the same way about “they’re all bad”–really hard choice this year. I went with the manager who “makes you wear her clothes, eat her food and say you’re grateful” because that story seriously buried the lede about the employee receiving a surprise independent contractor designation at the end of the year. I hate all of these managers, but I especially hate powerful people who wriggle out of their own damn tax obligations.

        BUT I hadn’t read the update to the mastectomy boss until I already voted. That update takes it to another level. What an awful human.

      3. Meepmeep*

        Yeah. I’d much rather work for anti mastectomy boss than daily therapy boss. I voted for that one. Two hours a day of mandatory therapy? Sounds like my vision of hell.

      4. Sarah*

        There is something particularly heinous about the daily therapy one because is an institutional decision, not just one bad boss. However, the mastectomy is the worst, I think, after reading the update.

    1. Cee Cee Dee*

      I honestly can’t choose. I wanted to go with mastectomy boss, and then there is the pee guy. Do you go with the the most callous, or the most disgusting? So hard to decide…

      1. Oranges*

        Pee boss is disgusting.

        Post mastectomy boss is evil. However medical lying boss is closer to my fear. So they won.

        1. Rayray*

          The one closest to my fear is the one that tells her she should be grateful for the job and makes her wear her clothes… Ughhhh. My boss is just crazy controlling and this definitely sparked a fear in me so that’s why I picked that.

          1. Yvette*

            Single White Manager? In case people don’t remember, there was a movie called Single White Female about someone who advertised for a roommate (ran a classified ad, “Single White Female looking for someone to share the rent”, that was how it was done in the US in those days.) and ended up with someone who basically copied her clothing style, hair style, tried to muscle in on her job and boyfriend, basically appropriating her life. That letter gave me the same creepy vibe.

            1. Catsaber*

              I had a boss almost exactly like Single White Manager – she stopped just short of making the young women in the office model the clothes – and she was constantly telling us how we should be “sooo thankful” to have jobs there. But mastectomy boss takes the cake for me – it’s just so bizarre that she is actively sabotaging the OP’s future employment. At least SWM didn’t try to stop me when I got another job.

          2. EPLawyer*

            That one was bat guano crazy. Making someone beg for their job after they had a serious accident is cruel.

            Pee boss is disgusting but you can just — not use the sink. Mastectomy boss is inappropriate. Which is bad. And the update was worse “here go sit in a corner with no resources but your work better be done to perfection.” But Single White Manager is just above and beyond. basically everyone else all rolled into one unbelievable terrible pile.

          3. Eukomos*

            Same, the wear her clothes boss and video call bosses called up some recent horrors I went through, so I had to go for one of them. Ended up going with wear her clothes since just reading that letter was so harrowing. They’re all nightmares though.

        2. Observer*

          Boss who decided that their employee is lying about their condition and is telling everyone that is ALSO evil.

        3. Works in IT*

          Yeah lying about medical condition boss is yet another brand of awful. Mastectomy boss is… really, really horrible, but I can vaguely see someone who has scar phobias being upset by that and having no idea what the appropriate way to deal with their phobia (hint: NOT punishing the person who had a double mastectomy) is. Pee boss is also gross, but… cultural differences? Maybe? Please?

          Telling someone to give you their medical records (so you can tell them they aren’t really sick?) then telling their coworkers they aren’t really sick when they refuse isn’t even vaguely justifiable. That is callous, no matter what the extenuating circumstances are.

          1. Observer*

            Both scar phobia and “cultural differences” sre stretching credibility waaay past the breaking point.

          2. Anonymous Poster*

            But… but mastectomy scars are under one’s shirt.

            I suppose a scar phobia’s possible – there’s probably someone out there with any phobia we can think of – but I think it’s rare enough to be a real reach. This is kind of ridiculous.

        4. First Star on the Right*

          Yeah, the boss lying about the LW’s health issues and mastectomy were tied in my mind, but the mastectomy update put it over the edge, for me.

          I’m sorry that that’s something you have to worry about. I know a lot of healthy people would brush that aside and say fearing that is an overreaction, but it’s a totally valid fear. I think it’s even scarier when people don’t believe you in a work context- it’s horrible when friends and family don’t believe you (I know that from personal experience, unfortunately), but when it’s work it’s more dangerous because it can impact your livelihood.

          1. Oranges*

            Yeah, the update totally made it harder for me. I’m going through some really fun medical stuff (finally got a diagnosis!) and my boss has been awesome but I just… oh gods. I don’t even wanna think about it.

        5. Elizabeth the Ginger*

          Pee boss is a gross *person*, but it’s not directly about being a bad *boss* (aside from the part where people won’t bring it up because he’s the boss). The others are doing management awfully, not just personhood.

        6. Red 5*

          I had a boss tell my co-workers I was lying about the reason I was out one day because I just wanted a day off and to saddle them with my work, so I had to pick that one because it’s still such a large grudge I’m holding.

          I can’t even imagine if he’d said I was lying about my health. I would have come down on that with everything I could think of…

          But mastectomy boss is just…especially after the update, I can’t even. UGH, vile and evil.

      2. sunny-dee*

        See I had to go pee boss. All of the others are some kind of normal horribleness taken to an extreme. But pee boss is just off the wall nuts. How does that ever even occur to someone, ever? At all? How does your mind go there?

        1. Zombeyonce*

          The only reason I didn’t vote for Pee Boss (and I wish they’d start referring to him that way in the office) is because I feel like it could be some mental deterioration (sounds like the weird stuff my grandma started doing right before she was diagnosed with Alzheimer’s) causing it since it seems to be a new behavior and it sounded like he was elderly.

          1. Close Bracket*

            How do you explain all the young dudes in this world who think peeing in bottle or something is an acceptable alternative to going to the restroom? Also dementia? Or just common but gross dude behavior?

            1. Zombeyonce*

              I’m going to say gross dude behavior. I’ll also say that I’m guessing all of them know better than to do it at work. Dementia often removes previously-held inhibitions, so maybe Pee Boss does this at home normally and is forgetting that he shouldn’t do it at work.

        2. Kate R*

          See, I didn’t pick pee boss because it doesn’t seem like ANYONE has actually addressed this with him, and while it should be obvious to everyone everywhere in the entire galaxy that pouring your pee on someone’s dishes that they eat off of us nasty as hell, I also keep thinking of George Costanza with “It’s all pipes!” I had a teacher in high school who would brush his teeth during our advisory period, and then spit in the sink behind my desk despite there being lots of other sinks to choose from (it was a science classroom). And I realize that’s not on the same level as pee, but I also felt like it should be obvious not to spit over your students’ heads. Like, we would literally be leaning out of the way so he could spit. He didn’t know it grossed us out until one day we finally asked him to use another sink (which we did in a very “we are disgusted” way), and he did. I also had an ex-boyfriend who would pee in a cup while driving instead of stopping at a rest area, which I also find gross. So my point is, some people legitimately don’t know they are being gross, and I don’t understand why no one in that office has tried even a soft, “Hey, would you mind pouring your pee out in the bathroom instead?” But OP just kept saying they are afraid he’ll deny it because he’s the boss or it’s their word against his, but he’s never actually deny it! Maybe he’s an unreasonable boss is other ways that indicate he’d take any mention of his pee cup harshly, but if he’s a normal old man who has this one extremely bizarre thing about him, why is no one even TRYING to broach this with him?

          1. Kes*

            This also part of why I didn’t vote for him – while this is something that is obviously gross to most people, it’s entirely possible he is just clueless and would stop immediately if someone said something

        3. I AM a Lawyer*

          I also felt like pee boss might be doing it on purpose just to see how far he could push his employees or something like that. Pee boss might be evil, too.

      3. Librarian of SHIELD*

        I can’t choose between the mastectomy boss and the one who made her employee wear her old clothes and beg not to be fired after she was hospitalized for an accident. They are both so horrendously bad.

        1. pope suburban*

          I’m torn between those two, and makeup boss. All three are so invasive, demanding, selfish, and frankly plain old crappy. I can’t imagine having so much as one semi-peaceful day working for any one of these nightmares. Though I am especially horrified by the mastectomy-hater, since the recent update was so so bad on its own. This year has been a real crop of terrible people.

        2. ClumsyCharisma*

          Those were the two I was debating as well. But mastectomy boss won out for me.
          I had a boss kind of like the boss who made her wear her old clothes (but she bought me new clothes that were no where near my style.) So I think she might have good intentions even though they are way off.
          Mastectomy boss is just evil.

          1. Librarian of SHIELD*

            Eh. The “wear my clothes” part was the least terrible thing about that boss. But yeah, the mastectomy boss is objectively a terrible human.

        3. DottyBlue240*

          Yes, while mastectomy boss is clearly evil, old-clothes-and-beg-for-your-job boss is a special kind of emotional and mental abuse. I’m having a hard time deciding which is worse.

        4. A Poster Has No Name*

          Yeah, this is where I am at. The pee boss is clueless and gross, but not nearly as actively harmful as many of the others. The casual cruelty and nastiness of the mastectomy boss and the boss who posts your fucking job the day after you get out of the hospital with broken ribs is just on a whole different scale than dumping pee in a sink.

          1. Scarlet2*

            Exactly. I think being evil and abusive is objectively so much worse than being gross. And anyway it’s just easier to avoid using the kitchen sink at work than to work with someone who’s actively dehumanizing and abusing you. Pee boss doesn’t even register when you look at those two.

            I had a hard time choosing between mastectomy boss and old clothes boss, but the awful update sealed the deal. I picked mastectomy boss because it just went from bad to worse.

        5. Observer*

          Oh, I forgot about that detail. That brings it from “dumpster fire awful” to evil as well.

          So much flat out badness here.

        6. Pomona Sprout*

          I was torn between Mastectomy Boss and Wear My Clothes Boss at first. Mastectomy Boss is arguably the most heinous of all, but I ended up voting for Clothes Boss, only because it just plain freaked me out in a way none of the others did. That one sounded like the plot for a very creepy movie and still gives me the shivers when I think about.

          I totally get why many people chose Mastectomy Boss, and it won’t bother me at all if it wins. On a completely rational basis, it was the most downright mean and evil.

      4. Anonymous Poster*

        It was a hard choice. I went with mastectomy boss because that person acted alone, in their right mind or as close as someone who does things like that has to it.

        I think pee boss is an unwell person being neglected, which makes his a story of “worst leadership” or “worst workplace” instead of “worst boss.”

      5. Ugh*

        It’s a sad day when a man who pours his pee down the sink on top of others’ dishes is not even the worst offender

    2. Data Analyst*

      Strongly agree – the pee boss is jaw-droppingly nasty, but even if making people see his pee is some sort of fetish for him (as some suggested), he’s still not evil like mastectomy-shaming boss.

      1. General von Klinkerhoffen*

        And you can decide not to use the workplace kitchen. Mastectomy boss made the entire workplace hostile.

      2. BrotherFlounder*

        This is where I went as well. So freaking nasty and disgusting. But it doesn’t sound like he’s actively sabotaging the person, unlike mastectomy-shaming boss.

    3. AnonEMoose*

      I had to go with mastectomy boss, because not only was the original post appalling, so was the update!

      1. Lizzy May*

        This. That update destroyed any chance I’d be voting elsewhere but every boss on this list is a nightmare.

        1. Hapless Bureaucrat*

          Yes. I was still very torn between masectomy boss and clothing boss but in the end the update proved mastectomy boss had a host of terrible management above them as well. I voted for the collective.

      2. Hills to Die on*

        Yes – the update pushed it over the top for me.

        I am still hoping that someday one of the nominees (or hopefully a worst boss winner) will recognize themselves and write in.

        1. Ellllle*

          Can you point me toward the update? I checked the original post and don’t see a link to it. Was it in a comment or something? Or am I missing something obvious!

      3. your favorite person*

        Yep, same. He wins because the update was terrible. I’m heartbroken for that poor woman. I hope she lawyers up.

    4. Barbara Eyiuche*

      I agree. Pee boss would be the winner most years, but while he is disgusting, his employees can avoid the pee by not using the kitchen. Mastectomy boss actually went out of his way to hurt someone recovering from cancer.

    5. Red5*

      I had to go with mastectomy boss, too. I mean, this woman just went through CANCER treatments, and not only did someone at her work complain that the look of her BREASTS — UNDER CLOTHING — made them uncomfortable, but her boss decided that was appropriate for him to counsel her. The unmitigated gall and misogyny of this puts it over the top for me.

    6. Detective Amy Santiago*

      The update to that one made it my obvious choice. Because I still can’t believe it somehow got worse.

    7. Audrey Puffins*

      Pee boss is absolutely disgusting, but mastectomy boss is a “perfect” storm of intersectional ableism *and* sexual harrassment. At least pee boss “only” pees inappropriately.

    8. Tink*

      Toss up between mastectomy boss and pee boss. I actually wish somehow they could all be officially notified that they made the list.

    9. Jules the 3rd*

      Hard choice for me between masectomy boss and ‘lying about illness’ boss. Are we including ‘constructive dismissal’ boss from the Update as the same vote?

      ‘Constructive dismissal’ boss is the worst, hands down, but ‘lying about illness’ boss is ‘constructive dismissal’ boss in waiting, and the masectomy jerk’s active emotional harm to a vulnerable employee, though totally awful, takes second place to active economic harm for me.

    10. Bananatiel*

      Thankfully it was one passing comment and nothing more but I had someone in my office tell me if was “confusing” when I switched wigs. I was post-chemo and the three wigs I chose to rotate between were the only fun I had with my appearance during that time of my life… so my vote is obvious but I’m pleasantly surprised so many others felt that sting without having to live it! Gives me hope.

      1. Observer*

        Someone actually said that to you? What are they – a toddler?

        That’s just so awful. But also, I would seriously be questioning their judgement and maturity as well.

    11. Secret Identity*

      I was going to choose mastectomy boss, but wasn’t the boss passing on what coworkers (or a coworker) were complaining about? Of course, the boss should have just shut the coworker(s) down rather than going to OP, but that felt like a bit of a mitigating factor in choosing who was, in fact, the absolute worst boss of the year.
      Ultimately I chose the boss who told coworkers OP was lying about the weather and her illness. Because that was just straight up maliciousness on the boss’ part rather than coworkers being jerks and boss passing on the jerkiness.
      Just my weird train of thought because I know everyone was eagerly awaiting my official opinion on this matter.

      1. Secret Identity*

        Ok, so maybe I was wrong. Somehow I missed the update. I guess I was kind of hoping the boss was just really, really misguided like they were a “by the book” type of boss that said to themselves, “Self, someone has made a ridiculous Complaint, and even though I find this Complaint ridiculous, I must still address it with OP because it is, after all, an Official Complaint and we must never, ever ignore an Official Complaint no matter what our personal feelings about the Complaint might be.”
        Ok, so maybe I’m doing some acrobatics to give Boss the benefit of the doubt. I don’t know why I do that. But I have now rescinded that benefit. I’ve already voted, though. Sorry. :(

    12. Elliot Kendall*

      See, that’s the worst *situation*, for sure, but part of that is having awful *co-workers*, too, not just a boss. I think pee boss edges mastectomy boss on that basis.

    13. Elizabeth West*

      They all suck, but I had to go with that one because honestly, you go through all that and survive, and then these fecking people come along. It reminded me of the colostomy bag coworker from Hell. >:(

    1. Hapless Bureaucrat*

      They really, really are. I suppose it’s a dishonor just to be nominated but I badly want to vote for them all.

  2. Misty*

    Given the update, I have to vote for “the manager who told an employee coworkers were complaining about the look of her post-mastectomy breasts”.

    1. Pilcrow*

      The update is what tipped this one for me. Boss retaliation, systemic corruption, and harassment, oh my!

          1. Rachel 2: Electric Boogaloo*

            Same here! I forgot about the update. Now I want to change my vote from pee boss to this one!

    2. What The Fork Is A Chidi*

      I agree, as soon as I read that option I just thought of the update and for me, it was a very easy choice

    3. CA in CA*

      Oh, same. The update to that one has actually kept me up at night. I wish I had the cash lying around to hire a lawyer for OP because man, that lawsuit would be wild it would make national news.

    4. Hapless Bureaucrat*

      Yes, it was the update that was the decider for me. That took it into ridiculously punitive territory.

    5. Felicia*

      The update definitely made it worse (which I didn’t even think could be possible) and made it a clear cut choice for me.

    1. Marthooh*

      Safari on iPad shows it as unreadable blue on gray. Press and hold to see red on white with a fingertip covering several words.

    2. Thankful for AAM*

      I dont seem to be able to vote? When I click the vote button it just spins and never seems to register the vote. Anyone else have this?

  3. Quake Johnson*

    These were all terrible, but thanks to the update the post-masectomy boss made herself come across even WORSE and jumped to the head of this race for me.

    1. kittymommy*

      I think that’s where I’m at. I was trying to decide between mastectomy boss and the lying about medical issue boss.

  4. Duke Flapjack*

    They’re not hardly as bad as in prior years. Bosses I want to work for? Hell no! Bosses that deserve x number of years in Purgatory? Perhaps not.

    1. ElizabethJane*

      I dunno, mastectomy boss is beyond the pale. Some of the others aren’t as bad. But that one… that one deserves all the years in purgatory.

      1. RUKiddingMe*

        Agreed! No one should be commenting on how her breasts look anyway much less post-surgery.

        Why the fuck ate they looking? Don’t they have work to do?

        And the boss doubling down basically saying “yeah, right don’t be lopsided…oh well you won’t capitulate to make people happy about how your boobs look…well let me illegally screw with your job.”

        I cant…

    2. Kes*

      That was my first reaction as well, my standard for awful bosses is so high (low?) due to past notables like liver boss and chemotherapy boss. However, on reading further, I do think some of this years are pretty awful too, including the boss who takes over your life and insists you be grateful, mastectomy boss and group therapy boss (who insists you disclose all your past traumas…to your boss)

      1. Hills to Die on*

        Liver boss is who I would vote for as the all-time winner, with chemo boss as the all-time worst runner up. Still want an update about that. if it ever happens, it will make my whole week.

        1. Coder von Frankenstein*

          Agreed, Liver Boss is the reigning champion for me. Hard to imagine that one being topped.

      2. RC Rascal*

        For me, both Liver Boss and Chemo Boss were intrusive, boundary breaking, overbearing, interfering, and seriously lacking in social skill. For me, Mastectomy Boss buts it over the top because in addition to all those things, they were also boorish, they violated employment laws and the OP was constructively dismissed.

        (This is my day to practice articulate ways to describe really bad bosses).

      1. Librarian of SHIELD*

        I mean, the LW from the “boss makes me wear her clothes and eat her food” letter did go back to work ridiculously soon after a serious accident because her boss threatened to replace her…

        1. I don't know who I am*

          I’d love to hear an update from that LW – hopefully she got a new job. That is a very messed up situation

      2. Observer*

        I’m not so sure of that.

        When a boss decides that THEY know what your medical condition is and then tries to pressure you into not handling your condition properly by spreading accusations about you around, that could endanger someone’s health because it can become a matter of “do I keep my job or take care of my chronic condition.” Similarly, when someone threatens to fire someone for the crime of landing up in the hospital.

    3. Jules the 3rd*

      The update to Masectomy boss, where they constructive fired the OP, actually puts this up to the level of Chemo Boss to me if you include it all as ‘one’ boss, though no one has matched Liver Boss.

    4. MoopySwarpet*

      Maybe a worst boss of the decade is coming up? Vote for the worst of the winners of the worst. ;)

  5. PJH*

    Another vote for “the poll doesn’t appear.”

    It seems Firefox has recently got a bit overzealous with blocking 3rd party scripts it thinks may be tracking.

    1. PJH*

      Figured it out – head to about:preferences#privacy and make sure “Standard” is selected under Enhanced Tracking Protection.

  6. Mama Bear*

    The top three are also my top three, but complaining to someone about her physical form after cancer surgery is just a bit more appalling than the others. That manager (the whole department, really) needs some sensitivity training!

    1. So long and thanks for all the fish*

      Idk, the one where after the LW broke her ribs her boss made her show up to work the next day, then posted her job and made her beg to take it down is pretty close.

      1. Hapless Bureaucrat*

        Very very close yeah. It was the fact that mastectomy boss had the apparent support of management that tipped it for me.

  7. TimeTravlR*

    So very hard to choose. My grandboss is ridiculous, but at least we can mostly work around him or ignore him. These bosses are beyond the pale!

  8. WellRed*

    So tough, almost went with the makeup one because its so sexist, but the post mastectomy one is inhumane AND sexist. I am on the fence about pee boss being included because I believe there were some age-related issues (If I recall, correctly).

    1. Person of Interest*

      I had to go with the makeup, because it’s just so pervasively and disgustingly misogynist, but about something so completely dumb. Really a symbol for all of the tone-deaf gender-biased bosses out there.

      1. LavaLamp*

        The makeup one makes me wonder what the job was, because if you work at Sephora or something that’s a job requirement that you have nice makeup. Otherwise, its really weird and I would probably do my makeup in the most outrageous way possible to annoy that boss, because I’m petty like that.

    2. Oliver*

      Yeah, I’m pretty torn between mastectomy boss and makeup boss as the Sexist Body Police. Makeup boss makes me more uncomfortable, probably because it was a policy of the whole company and not just one boss/department.

    3. Will!*

      I had the same line of thought, though I ultimately went with Gratitude Boss, because it’s terrible and bizarre, but also the only one that’s a straight-up crime. But I forgot about the Mastectomy Boss update with the transparent retaliation, and now wonder if I regret my choice.

    1. Slow Gin Lizz*

      Agreed. And for the boss who thought the employee was lying about snow or being sick, and the micro-manager who made her employee eat her food and wear her clothes. I want updates on all of those too!!

      1. sacados*

        Yes I REALLY REALLY want a lovely update from toxic wear-my-clothes-and-be-grateful-boss where we can find out that LW got out of there, got their taxes sorted, and now has a great new job in a sane and rational company!

    2. Hapless Bureaucrat*

      I want updates on all of these, even the two that updated. And I want those updates to be “I got the heck out of there AND I took the appropriate legal action” (if any).

    1. Heidi*

      It’s like how in another year, someone would have totally won an Oscar, and it was just bad luck that Daniel Day-Lewis made a movie that year.

  9. General von Klinkerhoffen*

    Mastectomy boss nudged it for me – because of the horrendous update.

    Strong field, unfortunately.

  10. Beebs*

    I voted, but really there are about 4 that are equally terrible for different reasons. But really, it’s an honor just to be nominated.

  11. Kes*

    I’m amazed the peeing in the sink boss is so high, it’s definitely gross but some of the others are way more actively harmful, and are awful *as bosses* whereas it would be gross if any coworker was doing that.

    I voted for the boss who was micromanaging not only her poor young assistant’s work but also her life (making her wear her clothes, etc) and then gaslighting her and insisting she be grateful, since that kind of abuse can have serious long term effects.

    1. [insert witty username here]*

      I voted for the same, for the same reasons. Masectomy boss is HORRIBLE, but that one is so CLEARLY wrong that I voted for the “SWF” boss because it was so psychologically manipulative.

    2. Third or Nothing!*

      Me too! That letter was so heartbreaking. It’s not like the others weren’t also terrible (one in particular that is the frontrunner right now is particularly egregious) but I just couldn’t let that one slide. I remember reading that letter the first time and thinking “oh honey no” so many times.

    3. animaniactoo*

      Ditto. That one edged out mastectomy boss, because she posted the OP’s job when OP had an accident on the way to work, because she didn’t call until AFTER she was released from the ER.

      … before work, I fell through a loading hatch on the street, broke two ribs and hit my head. I was in a daze the whole way to the hospital and by the time I was finished with my MRI, it was 45 minutes after I was supposed to be at work. I called Boss as soon as the doctor let me out and she was very upset that I didn’t call her right away. I got home, went to bed on painkillers, and sent her an email that evening detailing the whole story. I understand that she was worried when I didn’t show up, and apologized profusely and assured her I would be at work the next day. When I came again, she berated me for failing to call, accused me of not being grateful and not caring about my job, and actually posted my job on a hiring site and made me beg for her to take the posting down.

      1. Matilda Jefferies*

        Not just posted the job, but posted it and MADE HER BEG to take it down. I don’t actually believe in karma or the afterlife, but if anyone deserves to rot in hell for eternity, it’s this woman. What a horrible, horrible human being.

        1. Dragoning*

          My emotionally abusive mother liked to “punish me” until I grovelled and sobbed begging forgiveness, and her anger would be satisfied, at which point the punishment would be removed, and this felt a lot like that.

          1. KHB*

            I had an emotionally abusive boyfriend who would do the same. It sounds like there are a lot of us who had some buttons pushed by that letter.

        2. Elenna*

          Yeah, that bit is what pushed that letter to the top for me. Especially because it was OPs first job, which really made me wonder what kind of stuff they were normalizing.

    4. KHB*

      Ditto, ditto, and ditto. Awfulness that’s apparent to all involved is one thing, but awfulness that manages to convince you that it’s actually doing you a favor is on a whole ‘nother level, and it can seriously mess you up.

    5. CM*

      I think I voted for pee boss because the others were so emotionally difficult that I couldn’t choose between them, and that one was just disgusting.

    6. Jackalope*

      Yeah, I had to go with the emotionally abusive boss too. The mastectomy one was horrible, and the update was far worse, but there was something that just stood out to me about a boss who deliberately hired (from what we can tell) a young woman new to the working world and systematically treated her in such abusive ways. This could follow her for the rest of her working career bcs it’s the first chance she has to pick up working world norms (or one of the first; I can’t remember if she’d had other jobs or not). And while mastectomy boss was so obviously violating disability discrimination laws in the update and so likely will get in legal trouble if the OP goes that route, the other boss seemed just good enough at hiding it that she could be treating employees like this for the rest of her career.

      (Tough choice, though; besides those two I also wanted to vote for the makeup boss…)

    7. Phony Genius*

      Yes, remember that this is a “worst boss” contest. Not a “worst person” contest. They are not the same thing.

    8. Heidi*

      I also voted for this one. There was not only callousness towards the OP’s medical injury, but also the extreme distortion of professional boundaries and the possibility of tax fraud. And the OP was still trying to figure out a way to fix it all without hurting the boss’s feelings! It was a harrowing read.

  12. ElizabethJane*

    I voted for mastectomy boss but did we ever get an update on the boss who makes her employee wear her clothes?

    1. Dragoning*

      I don’t think so, because the boss probably invited her to her home for some reason and tied her up in the basement until she agrees to answer to the name of her long-dead child.

  13. IT Manager in Toronto*

    The pee is most disgusting, but I could avoid the kitchen and live with it. I couldn’t live with the twice daily therapy or the asking for a breast prosthetic. That’s toxic and harmful at an emotional and psychological level.

    1. JustaTech*

      The thing that was extra bananas about the twice-daily therapy was that it was at a *mental health clinic*! Like, if anyone on earth should know that this is not a good or useful or ethical thing to do, it *should* be people who are professionals in the field!

      1. WellRed*

        You would hope, but I think therapists can be just as uh, boundary challenged as the rest of us. Doctors and nurses also often make bad patients.

    2. Diamond*

      Yeah I voted therapy because I could barely manage a 5-minute ‘daily check-in’ where we were expected to get personal, so I can’t imagine TWO HOURS daily???

  14. She's One Crazy Diamond*

    This was a truly difficult choice! Went with the mastectomy though because they bullied someone already dealing with cancer.

  15. Aitch Arr*

    It was between Mastectomy Boss and Employee Is Lying About Their Health Boss, with You Should Be Grateful Boss in third.

    1. I don't know who I am*

      Those were my three also. I picked Mastectomy Boss but I’m still second guessing myself.

    2. Jules the 3rd*

      These were my three; I picked ‘Lying about Health’ boss, but only because I forgot to factor in the update. And I would not argue with anyone who picked any of these, they are all awful, just in different ways.

  16. emmelemm*

    Yeah, I’m in the “pee boss is awful and gross but mastectomy boss is pure evil” camp. But honestly, they’re all bad. All of them.

  17. Trout 'Waver*

    These seem pretty tame compared to previous years. All bad, don’t get me wrong, but not at the level of requiring organ donation.

      1. JustaTech*

        Somehow they’re more evil because they’re less obviously totally out of left field. Like, *obviously* I’m not handing over my liver. But these were close enough to reality that they clearly made the letter writers doubt themselves, and that by itself does a good bit of damage.

  18. pcake*

    To me, number one is the boss who tells your coworkers you’re lying about your health condition. It can affect your career for years to come, completely change how others see you long after you’ve left your jobs and impact relationships if people believe that boss. People who think you’re a liar about something like this and spread the word or whisper in the ear of friends at HR can really make your work / job search life suck.

    The rest are all truly horrid.

    1. Countess Boochie Flagrante*


      Paranoia about “disability fakers” is so widespread, and people are so eager to believe that someone isn’t actually suffering from a chronic health condition.

    2. Chocolate Trinity*

      Hard agree. I’m not surprised that Mastectomy boss is winning (and it’s easily my runner-up), but I’m shocked that lying boss is in last place.

      1. Coder von Frankenstein*

        Agreed. If I were ranking these, mastectomy boss would be first, wear-her-clothes boss would be second, and lies-about-medical-problem boss would be third.

    3. Ann Perkins*

      Yeah, the affect on relationships is what had me end up voting for this one. If the boss has influence in the community or industry, this could really hurt that OP’s career.

    4. Jules the 3rd*

      This was my vote, but if I’d thought more about Masectomy boss’s update, I might have picked that one. They all suck a lot, I’m not going to argue with anyone’s choices.

  19. Not Australian*

    I have a suspicion pee boss may actually have mental health issues, since that behaviour is so clearly not normal, and on that basis I’ve voted for mastectomy boss; that was an individual who had the capacity to behave well and deliberately chose not to. They’re both disgusting, don’t get me wrong, but pee boss may not be able to help himself; mastectomy boss could, but didn’t.

    1. Observer*

      I don’t think it matters. It just terrible behavior, no matter the reason.

      The only reason to not vote him to the top is because it’s less dangerous to the staff and minimally less awful.

  20. WantonSeedStitch*

    I’m still not sure Pee Boss isn’t suffering from some kind of diminished mental capacity. Mastectomy Boss is just a callous jerkwad.

    1. Coder von Frankenstein*

      I’m pretty sure Pee Boss *is* suffering from some kind of mental health issue. There’s just no other explanation IMO.

      1. Close Bracket*

        I have personally known a dude who peed in a bottle rather than use the restroom, and Tina Fey describes this behavior in Bossy Pants. This is a thing that some dudes do. It’s not about mental health issues. I don’t know what drives it except some bizarre boys-will-be-boys directive, but gross behavior isn’t always about mental health. I find it really interesting how many people refuse to accept that terrible, gross, and even criminal behaviors exist in ordinary people. It’s like some variation on the Just World Fallacy, or maybe even the refusal to accept gross behaviors in ordinary people is itself a mental health issue!

        1. FloralsForever*

          Yes, I agree with you here!

          The update was really telling – that people in the office were basically avoiding the situation. My guess is he would steamroll anyone who inconvenienced him, and that is a huge red flag. Maybe he’s not faced someone who has had a double mastectomy, or is part of a corporation that knows it needs to give its employees W-2s. But if he was, my guess is that he would also show to be a bad actor.

  21. Dee-Nice*

    Are other people choosing based on, like, objective criteria, or on which one makes them personally fill with the most rage?

    1. Rayray*

      I think so. I really hate mastectomy boss but the one that sparked fear in me is the one that tells her employee she should be grateful and wear her clothes. It just seems like a not too crazy reality for me and I hate my job already. That boss is just a notch crazier than my own boss.

      1. Dee-Nice*

        Right, these were my thoughts exactly! Mastectomy boss is probably/definitely going to hell, but I feel like I KNOW Grateful Boss and want to strangle her with my own hands.

    2. MuseumChick*

      When I’m stuck between two I go with “Which was the worst management?” as opposed to the grossest, weirdest, etc.

      1. Jackalope*

        That is a good point and perhaps why I didn’t go with video monitoring boss even though it was creepy and I’d hate it. I can imagine someone thinking that this is a good way to make sure your employees are in task. It’s not and a waste of time besides being horribly invasive, but at least I can imagine it being from poor management skills rather than malevolence.

        1. Jaydee*

          Bad management was actually the only point I gave video call boss. On a much, much smaller scale, I can actually see this being a legit way to observe a remote employee doing a task or process. But…like, in specific, isolated instances. “Hey Jane, on Thursday I’m going to pop on a video call with you and observe as you take a couple of customer calls. I do it in-person once every couple months with the folks here in the office to help with training and catch anything they’re doing really well or might need coaching on, and rather than driving out to your house, this seemed like a less-intrusive way of doing the same thing.”

        2. Iris Eyes*

          I felt like video surveillance boss wasn’t even the worse video surveillance boss this year and several of the others had the creepy overreaching element as well.

          I’m kinda surprised Hellmouth didn’t make the list with all the updates and craziness.

      2. JustaTech*

        I went with “in a position to know better, but chose something terrible anyway”, ie the therapy bosses.
        Either they know what they’re doing is harmful, and are doing it anyway (evil) OR they have no idea that therapy with coworkers is a bad idea, in which case they shouldn’t be directing anyone’s care.

    3. MuseumChick*

      Also, if there is one that is objectively evil (mastectomy boss) vs something that could be, say, a mental health problem (pee boss) or someone who just doesn’t know how to manage, I go with evil.

    4. Environmental Compliance*

      I went with the one that would be my personal idea of hell on earth that I could see happening more than at one random office – like, this could be something that becomes the New Big Workplace Idea.

      (It was the group therapy one. For mastectomy boss I would have no personal problem telling them exactly where to go and doing it very loudly. Group therapy would legitimately break me mentally/emotionally from a variety of past baggage. PeeBoss I’m going with mental deterioration, so it was hard to even include that one.)

      1. Troutwaxer*

        I went with the group therapy one too. It’s not just the intrusiveness or the ugliness, but the next step after that is blackmail central.

    5. Jaydee*

      I actually made a chart with categories and picked the one that I felt scored worst. The categories were:
      – racism
      – sexism
      – ableism
      – gross (both meanings) display of financial privilege
      – abusive behavior
      – general bad management practices
      – other legal/regulatory violations (overtime laws, FMLA, OSHA, etc.)
      – violations of a professional code of ethics
      – mitigating factors

      Only Pee Boss got a point back for mitigating factors, as if this was not a long-standing practice for him, it was probably related to some sort of physical or cognitive decline.

      Mastectomy boss got double points deducted for bad management practices because not only did he not shut down the complaining co-workers, he actually told the employee about about the complaints and expected her to do something in response to them.

      Makeup boss checked off every single form of “ism” and is a terrible manager. Her internalization of the patriarchy and enforcement of it on her employees makes me cry. Good thing I’m not wearing eye makeup today.

      The winner/loser for me was group therapy boss. This had the broadest range of problems. It was ableist. It was bad management. It was actually abusive considering the power differential between boss and employee. It probably violated overtime laws, and even if it didn’t it was a fairly gross display of financial privilege to expect employees to hang around after their shift without pay. And it was likely a violation of the professional ethics of a mental health practitioner. I did not give mitigating points for “but I was just looking out for my employees’ well-being” because the road to hell is paved with exactly those types of “good” intentions and because it would have taken only the smallest, most minuscule amount of reflection to realize that twice-daily mandatory workplace group therapy is a terrible idea.

    6. Anonymous Poster*

      I mostly narrowed them down based on desire to scream, but I based my final choice on the boss’s agency and whether I thought they knowingly chose to be horrible.

  22. Sack of Benevolent Trash Marsupials*

    I looked at it from the standpoint of who I would most hate working for, and the You Should Be Grateful boss won. I also had forgotten the part in that one where the LW sustained a *head injury* and still was yelled at for not, I don’t know, calling immediately after being injured?

    Mastectomy boss really should win though. Heinous.

    1. Jend*

      The You Should Be Grateful boss won for me as well. It was edge and edge with Group Therapy boss, but getting yelled at for a head injury was the tipping point.

  23. Countess Boochie Flagrante*

    Lying About Your Health Boss barely edged out Unacceptable Mastectomy Boss for me, only because the accusation of faking a health condition can dog you so badly in people’s minds.

    Every year, Alison, you manage to find a spread of such amazing scumbags for us to vote on!

  24. Phony Genius*

    Whoa. The order of the options in the poll changes each time you reload the page. So I can’t refer to them by number.

    Right now, I’m leaning toward the boss who makes you wear her clothes, eat her food, and say you’re grateful for your job. This is the only example here where it feels like you’re in a cult instead of a job. It would be the hardest to quit, psychologically, because of the sense of control you would feel that your boss would have over you. Read the OP to understand that this is already happening to the writer.

    However, with the other candidates, there is something to be said when an update is provided, and it seems to make the problem worse. I have to think about it before I vote.

  25. NewHerePleaseBeNice*

    Wow. A very strong field this year. I’m sorry I have to choose, but mastectomy boss gets my vote. Best wishes to all of the OPs of these awful bosses.

  26. Laura H.*

    I think we might need categories! They’re all awful, but there are some that you can work around (pee boss, Possibly the therapy boss) and some that are good lord no, I’m outta here yesterday (mastectomy boss w/ the update) And a cartoon villain boss category would add maybe a little lightheartedness to this austere assortment.

    Geeze. What an awful bunch this year…

    1. Bluenoser*

      Can you work around it? is one of my major selection criteria, That put Mastectomy boss front (especially post-update) followed closely by clothes boss with make-up and doubting illness boss tied for third.

      Therapy boss gave me pause, though, There are a bunch of potential solutions (talk to an ethics board, demand payment for coming early and leaving late, team up with your co-workers and all refuse to participate and, if all else fails, talk about the trauma of a favourite character) but it’s the one I can actually see catching on amongst the higher-ups in stressful industries who want to “fix” morale without actually changing the things that are causing stress.

      1. Meepmeep*

        Yeah, that’s why I voted for Therapy Boss. 2 hours a day of mandatory therapy is way worse than pee in the sink or a one time incident, no matter how awful.

  27. Kisses*

    Not voting the mastectomy one was tough- but I missed the letter about the woman in NY with the awful awful boss (wear her clothes, etc). It was just so far beyond anything and a combination of SO MUCH that I PRAY we get the best update in the world from her.

    1. Matilda Jefferies*

      Yeah, I just re-read that one, and now I’m all angry again. OP, if you’re reading, I hope you’re okay!

  28. anon24*

    Seeing as we’re coming to the end of the decade… after we declare this year’s “winner”, do we then throw all the “winners” from past years together and get to vote on worst boss of the decade?

    1. Christmas Carol*

      We could wait ’til March and then set up a play-off bracket. Could result in lots of lively discussion about seedings.

  29. Cruciatus*

    Just a reminder if you’re viewing in a browser in incognito or privately that you won’t see the options listed (this happens for me every year!)

  30. snarkarina*

    This was a tough call between one that is an objectively awful human being and one that I would rather die than work for. Ultimately, I chose the one that I’d rather not work for although another might be a worse human being.

  31. Krakatoa*

    Honestly, shaming a woman with cancer is so far above and beyond everything, especially after the update, that they should run away with this handily.

    1. AL (the other one)*

      The worst thing about this, is that it’s based in the UK. We do not have “at will” hiring/firing. We have national employment laws that should protect against this behaviour.

      It read to me like clear grounds for constructive dismissal (I appreciate that the OP may not want to go down that route).

  32. Sara*

    I hope we get an update on the ‘ungrateful’ boss – I really hope that letter writer got out and found a new job!

  33. Jaybeetee*

    Mastectomy boss for me – it’s just so *cartoonishly* evil, especially with the boss tanking LW’s reference so she can’t even get out of there?? Like, that boss isn’t just incompetent, and isn’t just pushing LW out – she seems to want to both fire LW and make it so she can’t work anywhere else either??

    Pee Boss was my second-place, because eeeeew. But I can at least avoid a breakroom and get on with life.

    I had the impression there were other awful bosses this year – off the top of my head, I can think of that LW whose dad’s GF was her boss, and the workplace that was fining people per minute late. IDK, maybe it was a “good year” for bosses?

  34. KR*

    Wow, really hard choice between the mastectomy one and the one who made OP beg for their job back after they got sent to the hospital.

  35. FormerFirstTimer*

    This is bananas! How am I supposed to choose just one?!? How did Alison narrow it down to just those choices? They’re all so bad…

  36. Coder von Frankenstein*

    I suspect that pees-in-a-cup boss is going to win out of sheer visceral revulsion. However, while I share that revulsion, I think I’m going to go with mastectomy boss – largely because of the update, which was dramatically worse than the original letter, and that’s saying a lot.

  37. Jubilance*

    Ugh, I wish I could vote for more than one! Alison, would you ever consider making the poll ranked choice voting? Cause choosing just one is so HARD!

  38. That Would be a Good Band Name*

    I really thought I was going to pick mastectomy boss, but I reread the letters and I just can’t get past the one who makes the employee wear her clothes, eat her food, and say she’s grateful for her job. That boss is flat-out abusive and so insidious that you could tell the employee was doubting their own instincts. The OP saying that it was easier to go along than to have the inevitable blow-up gave me chills.

  39. DarthVelma*

    I have been waiting for this post and the chance to vote and contemplating who I would vote for. I’d been thinking “pee boss” up until the update on the mastectomy letter. So I was pretty sure that was going to be my winner this year.

    Somehow I had missed the “wear my clothes and be grateful” letter. As someone who recently took a bad fall (I’m working from home today because my arms still won’t really bend in some directions I need them to to get properly dressed), that one really got to me. That boss’ reaction in that moment – I wouldn’t let “pee boss” empty his pee onto them if they were on fire.

  40. Sebastian*

    I can’t believe I’m writing this, but dumping-pee-in-the-sink boss was not my vote. Congrats, mastectomy boss, you are AWFUL, especially after OP’s update.

  41. Linzava*

    I just had to go with the boss that demanded gratitude. The 1099 thing pushed it over the edge for me, this boss is going to be an ongoing problem even after she leaves because of the tax thing.

  42. LadyByTheLake*

    I had to vote for the boss who was micromanaging not only her poor young assistant’s work but also her life (making her wear her clothes, etc) and then gaslighting her and insisting she be grateful. I had forgotten the part where the OP had fallen through a sidewalk loading hatch on the way to work and sustained serious injuries and the boss was angry at her (OP) for it. I had also forgotten the part where at the end of the year the boss gave a 1099 to a clearly W-2 employee, so hadn’t been doing any of the required withholding.

    Those pushed it over the edge for me.

  43. Bostonian*

    Ok guys, I know we’re freshly enraged off the mastectomy boss update, but holy moly I just re-read the letter about the boss who makes you say you’re grateful for your job…

    The letter writer had an accident where she HIT HER HEAD AND BROKE RIBS, and the boss almost fired her for not coming in or calling in sooner. (I’m assuming OP is female since the boss is female and made her wear her clothes/parade around in them.) That was in addition to constant criticizing and gaslighting, all while paying a laughably low salary and telling her employees they should be thankful for what they have. This boss sounds like an insufferable CONSTANT NIGHTMARE.

    I’m actually really torn between the 2 bosses on this one.

    1. Jan Levinson*

      I voted for the boss who makes you say you’re grateful for your job for the ‘broken ribs/almost fired for not calling in sooner’ incident. All of these bosses gave me rage to some degree, but nothing like that one did.

    2. Oliver*

      Yeah, I just re-read this letter and she might get my vote over mastectomy boss. She is full blown trying to emotionally abuse her employee.

  44. Jan Levinson*

    I’m really surprised that the Pee Boss is in 2nd place. His actions are absolutely disgusting, but don’t really give any indication as to how he is as a manager. The other bosses I feel would have more of a long-term negative affect on the OPs’ lives at work.

  45. Peaches*

    I’m just curious…does anyone know if any of the bosses who have been nominated over the years have ever come across Alison’s post, naming them one of the worst bosses, and perhaps reached out to her about it?

  46. Goya de la Mancha*

    It was harder to choose this year for me. I felt like there wasn’t a clear cut “winner” like previous years.

    Do we get worst boss of the decade round-up as we head in to 2020?!!?

    1. MuseumChick*

      For real, I want *all* the worst boss nominees to be put into March Madness-style brackets to see who would end up winning.

  47. Three owls in a trench coat*

    They’re all horrible. It’s just that some of them are more horrible or horrible for different reasons.

    Pee boss wins not for being the worst boss necessarily, but for being the worst excuse for a human being on this list. Even animals know not to poop where you eat.

  48. Rosie*

    I hope the person being forced to endure 10 hours of unpaid work a week on top of 10 hours a week of group therapy with co-workers (done by their line manager) on top of the regular working day is not feeling too hard done by these results – I mean, it’s nightmarish, and I hope to heavens they’ve gotten a better job, but at least they aren’t being bullied by their entire workplace and forced out of their role due to having cancer.

  49. Lars*

    Do we have a section for bosses we thought would get in but didn’t? Because I fully expected (fake?) snuff film manager to make the Worst Boss list.

  50. AnonyMouse*

    With the recent update, I knew mastectomy boss was going to be in the lead but I’m really surprised the twice daily therapy doesn’t have more votes. Maybe I’m just an exceptionally private person, but if that happened in my workplace I would be out the door so fast!

    Realistically these are all horrible. Also, updates from all of these would be great!

    1. Blue Horizon*

      I voted for that one. All the others I believe I could tolerate for a few weeks or months at least, but that one I’m not sure I could manage for even a day.

      That doesn’t mean it’s the worst, but it definitely pushes my particular buttons harder than any of the others.

      1. AnonyMouse*

        So come to think of it, the reason why I think I have such a strong reaction to that one in particular is because I may have unknowingly been subjected to something vaguely similar in a past job with an “ice breaker” at a team retreat. Old boss had us write down what we thought were important traits/experiences/interests that defined who we were as a person. Well, it got WAY TOO DEEP for the workplace! My boss shared that he had PTSD from his abusive childhood. A coworker shared that they were a sexual assault survivor. From there everyone seemed to be unpacking their past traumas and I felt like I was obligated to say something… so I shared that I have struggled with anxiety/depression in the past. Well fast forward a few months to a coworker who I thought I could trust exploiting that information to bully me behind my back. The whole office knew about it, but no one told me until long after she left so I had no chance of defending myself.

        Yeah, that explains why my gut reaction rereading this letter that is like “NOPE!!”

    2. Meepmeep*

      Yeah, that one would be the stuff of nightmares for me. I can avoid the break room to avoid the pee, and I can shrug off nasty comments about my body, but being forced to bare my soul for 2 unpaid hours a day – hell to the no.

  51. OlympiasEpiriot*

    I think we should have Australian Balloting here.

    Anyhow, I voted for the “You should be grateful” Boss because many, many years ago I had one of these. It was horrible and, for me, it was a different kind of horrible than the sexist pig boss, or the boss who never intervened in serious employee bullying, or bosses who demanded long hours while they were being abusive. I’ve never had a Therapy Boss, but, that seemed invasive on a level where I was torn between Grateful and Therapy.

      1. OlympiasEpiriot*

        Instant Runoff Voting. You get a ballot, you vote by ranking the choices. If everyone’s 1st choice doesn’t result in an outright winner (ie: no one gets more than 50%), then the candidate with the fewest votes gets eliminated and the people’s ballots who listed the eliminated candidate as their first get their 2nd place votes counted in the second round (and everyone else still is counted by their first choices). Results are checked to see if someone has more than 50%…if not, it continues the same way. When there’s only 2 candidates left, it is an “instant runoff”.

        A real boon for democracy is that this is probably the least susceptible to tactical voting — something the US elections tend to suffer enormously from.

        So, in this case, we’d have ranked our odious bosses. It would be a staircase of scum. A ladder of losers. A ranking of the rank.

  52. A*

    This played head games with me! In my opinion, one of these is the obvious winner (and so far voters seem to overwhelmingly agree). But because I’m confident that will be a landslide, I felt obligated to vote for my second choice because otherwise it would look like we don’t think they are that bad?

    Idk, mental gymnastics.

    1. Hapless Bureaucrat*

      No, I did the same thing. Even though logically I figure if you’re on this list that’s already proof you’re TERRIBLE, I somehow want to be able to affirm the terribleness of ALL of them.

  53. Hell in a Teacup*

    I haven’t left enough identifying info here yet so I’ll share this tidbit.

    My mom is a breast cancer survivor and she has relapsed after a few decades. Depending on how certain tests go for her and me I might get a mastectomy because it just makes sense to me. I can’t imagine working in an environment where that’d be an issue and I am not in a place emotionally where I could deal with it kindly.

    This was the easiest worst boss decision I’ve ever made.

    1. Tom (no, not that one)*

      I am sorry about your mom – and hope and wish for the best for you.

      It wasn`t easy – but that boss is indeed the worst (by a margin of 0.000001% above the ‘beg for your job’ one).

  54. Salsa Your Face*

    While all these bosses are objectively awful, therapy boss is the one that sets me on edge the hardest because it has the greatest likelihood of flying under the radar as “normal” company culture. It’s an absolute horror show of an idea, yet half the employees (all of whom presumably have no history of abuse, depression, or mental illness) seem to think it’s great for “team building” at the expense of the rest of their team. Therapy is intense and personal–which mental health professionals obviously know–and no one, whether they’ve been through something difficult or not, should ever, ever be forced to share that level of personal information with their colleagues or bosses.

    Everyone thinks pee boss is gross, and anyone working for clothing boss would be miserable, but some people (not here, but at the workplace in question) think therapy boss is okay and I’m using my vote to reinforce the fact that it. is. not.

  55. Meißner Porcelain Teapot*

    My personal ranking of awfulness on a scale from “Awful” to “Azkaban!”:

    7th: “Big Boss Is Watching You” Boss
    6th: “What Health Condition?” Boss
    5th: “Doll It Up or Get Written Up” Boss
    4th: “Let The Golden Shower Sink In” Boss (dear god, how is this only 4th place??)

    3rd: “Show Me On The Doll Where Your Daddy Touched You. Twice a Day.” Boss
    2nd: “I Find Your Lack of Breasts… Disturbing” Boss
    1st: “I own 98% of You and the Rest Belongs to the IRS” Boss

    Seriously. Re-reading all of those, I can’t help but give first place to the boss who made OP wear her clothes, eat her food, beg for her job after a major injury and then set her up for illegal tax shenanigans. Say what you want about the awfulness of therapy boss and mastectomy boss, but at least those two did not set their employee up to do something highly illegal and potentially insanely expensive.

    1. OlympiasEpiriot*

      I like the way you’ve summed them up.

      I also voted for the “I own 98% of You and the Rest Belongs to the IRS” Boss in first place.

    2. Tom (no, not that one)*

      Due to personal resonance – i have your #2 as my #1 and vice versa – but that was close (about 0.000001% difference).

      Otherwise, i second your order.

  56. GRA*

    Kinda wish “Hellmouth” could have made a surprise appearance on the list … those weekly updates were horrifying and stress inducing just to read, and I’m so glad she finally got out!!!

  57. PNWdweller*

    Is there an update for therapy boss? I am really hoping a licensing board got involved after skimming through the comments on the original post. I voted for mastectomy boss but these are all truly terrible bosses.

  58. raincoaster*

    I had a boss who told everyone including the regional vp that I was faking my illness (3rd stage cancer). This, after a coworker actually visited me on the cancer ward during a chemo session. She just didn’t want to carry the costs of an employee on long term leave, because it might cut into her bonus.

    A year later she was let go for faking an illness. Seven different managers, some of whom had never even met me before, contacted me to let me know. She was not a popular person.

  59. Urdnot Bakara*

    So many of these are SO BAD. My knee-jerk reaction was to go with pee boss, because just ew, but ultimately I voted for mastectomy boss because of how awful it was to LW directly.

  60. Cheesemonster*

    I can’t choose — each nomination exemplifies a unique facet of the horrible boss spectrum.

  61. Worker Bee (Germany)*

    What a year! If it weren’t for a particular update I would have had problems choosing the worst one. They were all terrible!

  62. hedda*

    I had Boss #1 last year. He couldn’t remember what he’d told to whom. His direction would change from week to week – in one team meeting he’d tell us to do one thing, and in the next team meeting he’d tell us to do the opposite. I ended up refusing to have one-on-ones with him because he’d forget what I said, and talk about me behind my back. I, too, have chronic health issues and working with this weathervane on it was impossible. He’d parrot back, and believe, whatever he was told and I had a coworker who told him I was faking it – so that became the story. He tried to blackball me from leaving when I looked at jobs in other teams in the company.
    Thankfully he got fired a little while after I left, but the constant gaslighting (“you’re one of the best employees on the team” to my face and everyone else hearing how little I did) left me with a good case of PTSD.

  63. hey anony*

    I had to vote for the group therapy boss, because although the mastectomy boss is hair-raisingly bad… there’s a good chance that HR will have Something To Say about that. Whereas group therapy sounds like something that might actually be an HR idea (a really BAD HR, but given the level of woo my workplace sometimes seems to cultivate, it seems possible). Meaning that there might be no one to report it to.

    But they’re all pretty dang awful.

  64. Roja*

    Mastectomy boss and group therapy boss… pity we can’t choose two. I sure hope all these LWs got out of their respective jobs.

  65. LGC*

    There were a couple that I vividly remember. And others that I wish I didn’t (looking at you, Pee Boss – actually no, I’m not looking at you because I’m not entirely sure that I can without experiencing Very Strong Feelings).

    Under the Jill Rule (i.e., which boss was the most consistently horrible over a sustained period of time), it’s clearly Mary (the boss that forced her employee to eat her leftovers and parade around in her hand me downs). But man, Boob Boss and Therapy Boss (who learned nothing from Jill’s campaign of terror) made it hard.

  66. Matt*

    I had to go with peeing boss for behavior that most people outgrow by age 2. If a boss at my company did that, I would have grabbed the cup out of their hand, thrown it in their face and called it my resignation letter.

    1. Tom (no, not that one)*

      Sounds reasonable – but as we learn on AAM – a toxic environment can warp ones perspective.

      1. Tom (no, not that one)*

        Side note – i don`t think that was the worst boss.
        Just the dirtiest, messiest boss with the biggest ‘YUCK’ factor i`ve encountered.

  67. Chocolate Teapot*

    I voted for the terrible Mastectomy boss, but there are several other awful candidates.

    The make-up one. If the boss wants the women to wear high heels and cosmetics, then there should be an allowance for it. Slightly off topic, but I once watched a Fly-on-the-wall documentary about training airline cabin crew, and one of the trainees was let go before the end because she kept forgetting to reapply lipstick.

  68. k*

    Every year my dilemma is choosing between worst individual boss person and worst company. I think Pee boss, whether he has unaddressed mental health issues or just gets off on a weird power trip, is a result of a company that lacks any structure for holding him accountable for his behavior, and probably work quality too. I think there were multiple people that let down the LW who had a mastectomy, the whole company is culpable and that useless union, too. If I was picking worst COMPANY, it would be the mastectomy one hands down. But I’m going super literal and picking the worst individual person, which has to be the small business “be grateful for my abuse” tyrant.

  69. CountryLass*

    They are all terrible, but I went for the one who made her employee BEG to keep her job, and yelled at her for not calling work before she got rushed to hospital. I mean, WTAF??

    The (current) top one of the post-surgery breasts is atrocious, and I did seriously consider that one, but something about being forced to wear her cast-offs and constantly say how grateful they are just reminds me of abuse stories.

  70. Tom (no, not that one)*

    Okay, seriously – this is an almost impossible choice.
    Is there some kind of school of management that teaches ‘negative attention is great’?

    Is ‘abuse your employees’ some mandatory training for managers these days?

    Frankly – as i could only choose one – i`m now shaking with anger at the evil of some of these (alleged) humans.

    My choice is the masectomy post – as besides abusive, callous, insensitive, coldhearted, it struck a chord as I lost a good friend to cancer, and we (my wife and myself) have some breast cancer survivors in our circle of friends.
    But, the ‘beg for your job’ one was a very very close second (think about 0.000001% smaller) – but as you cannot vote for 2 or more…

    I would really like to know about WHY these “managers” act the way they do – though I may not like the answers.
    Because, a normal functional responsible person wouldn`t do/say the things that the letterwriters describe, right?

    To all the victims – I wish you a better 2020 (though, with some managers – this isn`t hard).

  71. Carlie*

    I had to go with the “you should be grateful” boss because as bad as the others were, at “least” they were bad in a single, specific type of situation. Grateful boss was terrible across the board in all aspects of employment and outside into the employee’s personal life and choices.

  72. The answer is (probably) 42*

    I see that some of these have updates that haven’t been linked in the original post yet (like pee boss), but I cand find for some of them. Did we ever get an update on any of these besides for pee boss and mastectomy boss?

    Voting results aside, I want to hear if all these LWs are ok!

  73. kib*

    I don’t get why the boobs boss is winning by so much when the “boss who makes you wear her clothes, eat her food, and say you’re grateful for your job” is so much worse. Like that person went to the ER and then had to beg for their jobs posting to be taking Dow ! And had to wear her bosses clothes!!

  74. Fox in a Box*

    I voted for the pee guy because it felt like the worst impact on the office as a whole, but mastectomy boss is definitely the worst impact on a single person :(

  75. Rob aka Mediancat*

    I picked the boss who makes her employee wear her clothes and say she’s grateful, because honestly, she seems like the worst BOSS out of the group of them — the post-mastectomy boss is the worst human being, but based on the update that whole culture sounds horrendous, and the boss seems to have been merely a symptom rather than the issue themselves.

    The first one is someone where I would prefer any boss short of the Joker.

  76. Anonymous from Seattle*

    Wow, no way to vote for the boss that laid me off because they thought I was incompetent when I had an ongoing health condition that worsened my mental health condition? Thanks Deloitte.

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