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The 10 Most Horrible Bosses of All Time

Updated February 27, 2020 5.1k votes 1.7k voters 859.4k views10 items

We've all had a bad boss or two, one that makes us stay later than we want to, doesn't pay us enough or makes us do demeaning things like take out their trash when it's full. Bad bosses get a lot worse than that, though. From firing an employee who just donated a kidney to the boss to one that made staffers tattoo his birthday on their necks, to one who installed sniper towers and canons when workers asked for a raise, these are the worst, most horrible, bad bosses of all time.

Who are the worst bosses ever? If you think you've got it bad, just read a few of these and come into work tomorrow morning at peace with the fact that your bad boss isn't going to fire you over liking a Facebook page. All of the bad bosses you've ever had likely don't even compare to the worst bosses of all time. And if they do, maybe it's time you looked for a better place to work.

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  • 5

    Employee Fired for Liking a Facebook Page

    Library of Congress employee Peter TerVeer logged into his personal account, clicked the "Like" button on a Facebook page called 'Two Dads.' It's just what it sounds like - an LGBTQ+ page. 

    His manager John Mech, keeping tabs on TerVeer's personal Facebook use, took note of the new activity. Mech subsequently began giving TerVeer poor performance reviews and made some derogatory comments about his sexual orientation to other staff members. Things got so bad that TerVeer's therapist recommended that he take a leave of absence, which the Library of Congress agreed to.

    When TerVeer came back, however, he was sacked, and guess why? You got it: For missing 37 consecutive days of work.

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  • 6

    Boss Breaks Employee's Nose While Forcing Her to Kiss Another Worker

    What do you imagine goes on behind the shiny white doors of Vogue? You probably didn't imagine anything like this:

    In 1999, publisher Richard "Mad Dog" Beckman was out with employees when he decided he wanted to see two female employees smooch. He chose West Coast ad director Carol Matthews and Vogue international fashion director Emily Jahncke Davis. Beckman pushed the two women's faces together so hard, it broke Matthews's cheekbone. She ended up in need of extensive reconstructive surgery. Beckman apologized, but Matthews sued anyway. She settled out of court, and may have gotten close to her asking price of $10 million.

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  • 7

    Boss Uses Employee Credit Cards to Pay for Fuel for His Private Jet

    Lenny "Nails" Dykstra was a center-fielder for the New York Mets in the late-1980s and the Philadelphia Phillies throughout most of the '90s. Some years later, in 2008, he started a magazine called Player's Club about professional athletes and their expensive lifestyles. He even offered them financial advice.

    The problem was that Dykstra was still living one of those expensive lifestyles even though he was no longer an athlete. In 2008, his net worth was estimated at $58 million. In 2009, he filed for Chapter 11 bankruptcy, listing less than $50,000 in assets. He claimed to be a victim of mortgage fraud, lost a house to foreclosure, and was the subject of at least two dozen legal actions since 2007. 

    In addition to his myriad personal issues, he was a bad boss. Dykstra had a reputation for pestering employees at all hours of the night, even inviting prospective employees to dinner and stick them with the bill. But those were still small potatoes. The unluckiest employees were pressured into providing him credit card access with the promise they would be paid back with interest. "One of the dumbest decisions I ever made, giving him my American Express card information," said Kevin Coughlin, who left another job to become photo director for The Players Club.

    Coughlin said that Dykstra ran up tens of thousands of dollars on his card, including one $32,000 charge for a leased jet from Atlanta to Helena, Mont., where Dykstra’s son, Cutter, was playing minor league ball. Coughlin worked only 67 days for Dykstra, but it took months to recover the money.

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  • 8

    Boss Exploits Former Employee/Wife

    Shelley Lynn worked at McDonald's, which offers minimum wages, no benefits, and weak job protection. Lynn met Keith Handley in the early 1980s when she worked the counter at a McD's in Arroyo Grande, CA. At 29, she already had three children and had been divorced three times, so she was happy to meet franchise owner Handley. He was educated and older. And he stood by the manager when he fired Lynn for not putting ice away.

    After her termination, Handley began taking Lynn and her children to McDonald's every night. A relationship developed and Handley bought a house for Lynn and children in Las Vegas. However, as bills associated with the home mounted, Handley convinced Lynn to engage in sex work as a means of supporting her family. 

    At the end of 1986, Handley took Lynn to Chicken Ranch Brothel in Pahrump, NV, where she worked for the next six years. 

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