the worst boss of 2019 is…

by Alison Green on December 19, 2019

We have a winner! 16,049 votes are in, and the worst boss of the year is the manager who told an employee coworkers were complaining about the look of her post-mastectomy breasts — with 44% of the vote.

The six runners-up, who managed to be pretty terrible themselves:

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    1. EPLawyer*

      It takes real effort to come out as worst boss of the year, considering all the contenders. Kudos for those who go the extra mile to really suck.

  3. Kimmy Schmidt*

    I feel such a bizarre sense of camaraderie with the 16000+ other individuals who read through all this awfulness and came together to collectively WHAT over everything.

        2. Flyleaf*

          The Consumerist web site used to award a gold plated piece of poo to the “worst company in America.” Maybe something similar?

    2. Third or Nothing!*

      Can it be a statuette that has clearly had a single mastectomy? We can model it after my mom. Or my grandmother.

      3. Snuck*

        A gold painted Barbie with only one boob and mussed up hair… Give me five seconds and I’ll hand Mr 6 a pair of scissors and something out of the toy box :P

        Sigh.

    5. Three owls in a trench coat*

      In addition to these excellent suggestions, may I propose a plate of cheap ass rolls that have been decorated to look like boobs.

      1. Third or Nothing!*

        Don’t you be disrespecting the winners! You bring those good rolls! Hawaiian or nothing!

        2. Snuck*

          +2

          (The best thing about these end of year mash ups is the in jokes and the shared memory of so much dysfunction!)

  5. Jennifer*

    I tried to get a win for pee pee boss. We couldn’t get it done. But remember, if the winner cannot fulfill his duties, the first runner up will assume the title.

      2. Working Hypothesis*

        I had a hard time with this one — they’re all pretty impressively awful — but I had to go with the boss who required twice-daily group therapy. It’s not just that they did it; I reread the whole letter and it’s all the horrific little details (questionnaires that go to your manager about whether you’ve ever been sexually abused?) that made it so impressively terrible. But Pee Boss was the second. The mastectomy thing was a truly dreadful thing to say, no question — I just get personally more creeped out by the long-lasting policies or processes, myself.

        It’s a good (bad) crop of candidates this year, as we usually seem to get… it’s slightly depressing how reliably we end up with a really appalling collection of choices for this award!

        1. Snuck*

          I struggled to vote too… I wanted to do a first / second / third (like Australian polling, with preference deals hahahah).

          I went with the mastectomy first… but the video camera second (in my mind)… it’s interesting how the level of dysfunction we’ve witnessed ourselves plays out in our minds…

    2. Quill*

      He is 100# the runner up but Mastectomy Boss won because it combined so many different kinds of WTF into one prosthetic boob shaped package.

      3. Veronica Mars*

        Yeah, I mean, I get that pee-pee boss is gross. But he wasn’t… actively expending serious effort to be horrible to other people. It was driven by laziness / mental issue, not outright vileness.

        1. Pay No Attention To The Man Behind The Curtain*

          Exactly. He wasn’t like peeing on people as a show of dominance/punishment or anything — he was just grossly thoughtless. Mastectomy boss was maliciously vindictive and awful specifically to someone who was already going through a horrible experience.

        2. StrangerThanFiction*

          Yeah, pee-in-the-sink boss is kind of a one-trick pony – you can avoid his special brand of not-as-we-know-itery by not going near the room where he dumps his stuff. A manager with real aspirations for the award would be expected to demonstrate the skill to invade your entire working day, with bonus points for not allowing you to leave it behind when you go home.
          I must admit, my favourite was be-grateful, wear-my-clothes boss, but that was at least partly because of a couple of comments on the original post, which quite rightly didn’t assume the gender of the OP when it wasn’t specified. The picture of a male worker parading in front of the (specified as female) boss wearing her discarded clothes, detached my already over-WTFed brain from its moorings and plopped it into a vat of freshly-steaming batshit.
          On the whole, I agree with the general verdict, but given the above, I still think the wear-my-clothes boss has potential do do the full Stephen King and be a future winner to the surprise of all who weren’t paying attention this time round.

          1. Immunocompromised. Voted for Pee Boss.*

            Ah, but that’s the question about Pee Boss: is he really a one-trick pony? Where else in the office might he be pouring bodily fluids, unbeknownst to the rest of the employees?

            It would haunt my dreams.

    3. Seeking Second Childhood*

      It was the updates that did it for me — that whole *company* dug itself deeper and deeper over time to win this boss his award.
      Alison, if OP gets co-workers together in January 2020 to ask pee boss to stop doing what he’s doing and he doubles down and gets even more offensive, is he eligible for re-nomination next year?

        1. Elizabeth West*

          I agree with many bells down’s comment on the update that everyone in OP’s office get yeeted into the sun.

    4. Laura H.*

      I am such an eight year old when I appreciate the juxtaposition of “pee pee boss” and “duties”.

      I’ll show myself out!

  7. Quill*

    You know, I think that the reason Mastectomy Boss won is because it combined the themes of so many of the others: Medical shittiness & descrimination (See: ‘boss who tells coworkers you’re lying about your health condition), Sexism (‘boss who requires women to wear perfect makeup’), and bizzare gaslighting (‘twice daily group therapy at work’ and ‘say you’re grateful!’)

      1. Detective Amy Santiago*

        Agreed. I am still completely and utterly baffled at the fact that the situation got worse. I am a creative person and I could not have imagined that happening.

      4. Nic*

        Agreed. I think the update cinched it.

        Especially given that Gratitude boss combined a lot of the same factors (minus the cancer/misogyny but plus a toe-curling level of sadism in forcing the LW to grovel for her job after missing one day of work because she was taken to hospital after an accident) as Mastectomy Boss, and yet she only came in third behind the Pee In Sink Boss which also had a recent update.

        1. Elenna*

          Yeah, I voted for gratitude boss because I forgot about that update! And also because the level of sadism/gaslighting was so terrible (seriously, LW was in a serious accident and the boss made her *beg for her job*) and it was LWs first job, so one has to wonder what kind of terrible norms she was internalizing…

      5. ampersand*

        Ooooh I missed this update. I’ll go back and read it…and be prepared to get angry all over again, from the sound of it.

        Makes sense now that mastectomy boss won! I didn’t get around to voting in time, in part because I wasn’t sure which boss was the worst. It was a tie in my mind between mastectomy boss and compulsory twice-daily therapy, which is so so egregious.

        Off to read/be angry!

        1. ampersand*

          Welp, y’all weren’t kidding. That update was INFURIATING! The poor LW. For all our problems as a country, that crap would not fly in the US. I hope she later has a happy update full of schadenfreude-y goodness.

    3. Phony Genius*

      And that one looked more like it would qualify as “worst employer,” as there was some than one person involved, not just the immediate boss. Maybe we need separate categories for individuals and companies/organizations.

    5. cmcinnyc*

      Yes. This one managed to touch all the bases and bring it home. But that takes nothing away from the specific awfulness of our losers. They are ALL losers, every one.

  8. Audrey Puffins*

    If we come together, we can achieve ANYTHING. Now, let’s send the mastectomy boss OP all our energy in the hopes that she gets an incredible employment lawyer and some fantastic justice in the new year!

    2. Not Australian*

      Absotively, posilutely. I don’t think I have ever been quite as invested in wanting a positive (and hopefully devastating) outcome for an OP as I am in this instance; the injustice – and the downright unnecessary cruelty – involved just seemed so egregious.

  9. Daphne Moon*

    I was so torn between the winner and the boss who made the employee beg for her job. In the end I had to go with what was so flagrantly illegal.
    To the employee who had to beg/wear the boss’s clothes/etc.: please update us!

    1. OtterB*

      I voted for the boss who made the employee wear her clothes because (not highlighted in the headline Review of Awfulness) she made the employee beg to have her job taken down from a job search site WHEN THE EMPLOYEE CAME TO WORK THE DAY AFTER HAVING BROKEN TWO RIBS IN AN ACCIDENT.

      Although there were a depressing number of qualified candidates this year. (Or should that be dysqualified?)

      1. Nic*

        I voted for her too. The others were awful bosses putting their employees in terrible and sometime illegal positions … but that one was an emotional terrorist of a pantomime villain, who was one step away from abducting puppies to make clothes!

    2. Brett*

      I really hope we get a positive update some day from the OP in that one. She sounded much more hopelessly trapped than the other letter writers, especially with the 1099 bombshell that her boss dropped on her (disqualifying her from collecting unemployment if she gets fired). The OP should have been sending both the IRS and state unemployment agency after her boss for that one.

    3. Aquawoman*

      But they BOTH had flagrantly illegal aspects to them! Mastectomy boss had all of the clearly ADA-violating nonsense and gratitude boss misclassified an employee as a contractor.

  10. Grey*

    Worst Boss of 2013 contest had 1,975 votes. This year it’s up to 16,049. Goes to show how popular this site has become.

    1. StellaBella*

      I was thinking this the other day in terms of site metrics at a glance – some of the letters and comments had less than say 100-200 comments (looking back at 2014 letters or 2013, for example), and the traffic has just ballooned! CONGRATS Alison on the terrific growth and managing it all!

  11. This Gand*

    I feel like my biggest accomplishment of 2019 may be that I successfully predicted on January 7th 2019 that we were a week into the year and this year’s competition was already effectively over.

  12. MuseumChick*

    I think the fact that the boss who watches you by video call while you work only got 4% of the vote shows how utterly egregious this year’s pool of bad bosses was.

    1. Quill*

      That’s because everything else was multiple factors of awful! (We also didn’t get an update on this one…)

    2. Kes*

      To me that’s the remote version of omnipresent micromanagers which is a somewhat more common theme though – as creepy and orwellian as it is, the others stood out as more unusually bad

    3. cmcinnyc*

      If we get an update that Spy Boss went on a round of medical gaslighting and demanded that LW wear makeup to work from home, we can petition for a re-nomination in 2020.

  13. The Guacamolier*

    But we all know it was really the boss who only celebrates the employee with the leap year birthday every 4 years. (While every other employee gets their birthday off with pay.)

      1. EPLawyer*

        You win.

        Yeah, not only was that person clueless, but they wrote back and DOUBLE DOWN on why they were completely justified in going to the letter of the calendar.

        1. whingedrinking*

          If that person wrote in again and said, “One of my employees is angry that I denied them parental leave, but they’re just *adopting* a kid, they’re not really becoming parents”, I wouldn’t be at all surprised.

  14. HailRobonia*

    I wish we could send this boss a prize. What do you think would be fitting? Maybe a plaque that says “it’s better to be missing a boob than to be missing a brain”?

    2. MuseumChick*

      How an AAM Certificate? Make it all fanacy and have it say “By the Powers Invested by the Internet the Illustrious Alison Green Herby Confirms you as the Worst Boss of 2019.”

  15. LGC*

    …if ever there was a year where “congratulations, you all suck” applies, this is it.

    (My vote was for Clothes Boss, because she also berated the LW for falling and breaking her ribs. But Mastectomy Boss – or, because I like alliteration and I’m a 12 year old boy, Boob Boss) is a WORTHY winner because the entire company reenacted the bird phobia letter with a side of discrimination.)

  18. Lady Phoenix*

    It was a simple matter for me.

    Yes, pee boss is awful and making a health hazard (see the WTFIWWY episode “Let It Snow” where they talk about why pee is gross). Make up is sexist and needs a good boot to the arse. The one who demanded OP be her clone is… weird.

    But the Masectomy boss did something inhuman, degrading, and EFFIN ILLEGAL TO THE HIGHEST DEGREE. I am still wishing poxes on the conpany’s houses and a slew of dragon fire on their bodies.

    I hope in the second update, OP delivers some divine retribution.

  19. ResuMAYDAY*

    Did we ever get an update on the boss who made her employee wear her clothes, and beg for her job after landing in the hospital?

    1. Anony Pony*

      This is what I am looking for, as well but I didn’t find one when searching the past updates since June. I hope they see this and gives us one!

  20. The IT Plebe*

    You know, this site has been around for awhile and it’s 2019…if it’s possible (and totally understandable if it’s not!) I’d love to do a Worst Boss of the Decade vote. All the comments talking about previous Worst Bosses has me wondering who’d be Worst of the Worst.

    1. The IT Plebe*

      Forgot to mention (although it might be obvious) that the contenders would be all the previous Worst Boss of the Year winners…assuming you started this in 2009.

      1. Heidi*

        Tournament of Champions! Mastectomy boss vs. making you go to couples therapy with your dad boss. Who will win this head-to-head battle of the all-stars?

      1. Ferret*

        Eh I feel like Chemo boss and Grave Note boss could give him a run for his money. And possibly Couples Therapy with Dad boss although the happier update means I feel somewhat less strongly even if it doesn’t change the wrongness of the original behaviour

        Liver boss was clearly awful (and actually fired a pregnant woman who didn’t get tested if I remember correctly) but there was at least a clear way of getting out of it (by letting the testers know you were being coerced) and might possibly be able to claim temporary insanity due to grief – not that that justifies the behaviour but if we have to rank the pile of awfulness we need to start somewhere…

    3. Kes*

      I agree, that would be amazing. I was just going back through past years’ and there are some strong contenders (chemo boss, liver boss, grave note boss). The only challenge would be deciding who to put in since some years had multiple especially bad ones (looking at you, 2016) but you don’t want to flood the poll with too many options.

  22. Freddled Gruntbuggly*

    Yes, please; was preparing to post this same request, difficult as it may be to choose Worst of of the Worst, amongst so many appalling examples vying for the nadir of behavior.

  23. I'm that person*

    I would like to call up the “winner” and say, “Congratulations, more and twice as many people think that you are a worse boss than I guy who pees in a cup and pours and in a sink.”

  24. redflagday701*

    I’m kind of surprised that Pee in a Cup Boss came in second! He’s gross as hell, but still not terrible-terrible to me — especially in terms of abuse of power, which seems like a key factor in this contest — as any of the others.

    1. DirectorofThings*

      I agree. It was almost impossibly gross and weird, but does not create the kind of all-encompassing employee misery that exists when a boss is manipulative and terrible. Still gross and still not something I would want to tolerate, but less worse than the worst bosses/companies on here. So many losers!

    2. Close Bracket*

      I feel like Pee Boss *was* abusing his power, in the sense that bosshood and other forms of power lead to an entitlement mentality where the boss believes normal rules don’t apply to them. I mean, I don’t have my copy of the social contract on hand to look up the appropriate section, but I’m pretty sure confining your eliminatory functions to the bathroom is a normal rule.

    3. whingedrinking*

      I think it’s the sheer egregiousness of Pee Boss. It’d be like if one of your coworkers came to work naked one day.

  25. whistle*

    Maybe all the nominees can get together for therapy twice a day to talk it all out. We can dictate the clothes they need to wear and ensure the only available bathroom is the sink. And of course we get to watch via webcam.

    1. Wren*

      I’m not sure that “get” to watch is the right phrasing here. I feel like “are forced to” watch would be more accurate. Not shaming your kink, just sayin’.

  26. Rivakonneva*

    The old TV show Laugh-In used to give the Flying Fickle Finger of Fate Award to various politicians and businesses that really screwed people/did outrageously stupied and ill-conceived things/etc.

    Maybe we could bring that back for Mastectomy Boss with a specific finger raised in his ‘honor’. :)

  27. The Other Alice*

    I was rooting for Sink Pee Boss but I think last week’s update really cemented Mastectomy Boss’s lead. He was also winner(*) of Most Infuriating Update and of I Really Hope There Is An Update To The Update Where He Gets Sued And Fired And Bitten By Many Mosquitoes.

    (* in my heart)

  28. RB*

    Is there also a favorite letter of the year? I can’t remember if we usually do that. I vote for the Hawaiian Rolls letter.

  30. Sharon H*

    I really want the woman undergoing breast reconstruction to say to her co-workers and boss who find her lopsided top inconvenient: guess what, breast cancer is inconvenient, get over it. To that I will add, grow up.

  31. MJ*

    As bad as these are, I’m betting we’ll have the first contender for 2020 in January – and it will be as bad if not worse than these.

  32. BananaSalamander*

    I’ve been following this site for a while and this is definitely the hardest decision we’ve had to make on this. The bosses this year were so, so, so, so bad. Yikes!

  33. whingedrinking*

    I just realized that this site has a tag which reads simply “jerks”, and I’m so here for it.

  34. Beatrice Cup*

    That post mastectomy comments one was worse than I expected. Like I was expecting that it was a female manager thinking she was entitled to comment on another woman’s breasts because they’re “all girls here,” but no, it seems like it was the sort of immature men who don’t want to be reminded that women’s parts aren’t all sexy all the time. Our genitals bleed and carry babies. Our boobs feed babies. Sometimes our boobs try to kill us. And here is someone who’s been through a painful experience and they want her to pretend everything’s OK for their comfort. That would be like if a man got kicked in the balls and the female bystanders reaction was hey can you please hide your pain and stop reacting because it’s not sexy to me to see a man crying.

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