5 CEOs Caught Being Petty As Hell

5 Casey Bloys

Casey Bloys might not have the name recognition of some of the other CEOs on this list, but you’re certainly aware of his company, HBO. At least, until they decided to set that storied name aflame in order to launch whatever exactly “Max” is, and make parents across the country think someone hacked into their Roku. Bloys was made CEO in October 2022, but only a few months earlier, he’d been taking some extremely small battles into his own hands.

Some people deal better with criticism than others. It’s never fun to be told precisely in which ways you are lacking. If you’re on the internet reading the work of CRITICS, though, what exactly did you think you were going to get? Nevertheless, online criticism of HBO programming apparently cut straight to the quick of Casey Bloys, and he officially recruited employees to create burner accounts to strike back at online critics. It all came out in a wrongful termination lawsuit by one of the employees forced to make these burner accounts, all of which was apparently worth the catharsis of two-like, limp online zingers from clearly fake online “herbalists.”

4 James Dolan

If you’re someone who bristles at public criticism, possibly the worst thing you could do is own a terrible sports team, especially one in a major media market. If you own a beloved team like the New York Knicks, that is based in a city with enough journalists that most pigeon shits don’t go uncovered, you’re going to hear about how they’re doing. Watching a storied franchise collectively lay a fat one down the middle of the most famous venue in basketball during home games isn’t a path to New York royalty.

Nevertheless, owner James Dolan, who has likely just arrived at this article from Google, seems to think the idea of fans wanting their team to win some games is childish and unreasonable. One punishment Dolan is fond of doling out is a ban from his venues, like the one bequeathed to a fan who yelled at him to “sell the team.” He took it a step too far, however, when he started using facial-recognition software to enforce his little take-your-ball-and-go-home declarations. Because keeping the mean guys out is definitely worth sparking a civil rights lawsuit.

3 Steve Jobs

Look, I love my phone as much as the next guy, and I’ll admit to a bit of dismay when a green bubble gets added to my group chat. On a pure evaluation of business and technological innovation, it’s undeniable that Steve Jobs is one of the most impactful people in history. It’s also increasingly undeniable that the guy was a massive dick.

There are arguments to be made about the need for CEOs to be unsentimental (READ: be a dick, business-style). For example, for the good of the business, sometimes you need to fire people, regardless of your personal relationship or how it will affect them. Doing that in an auditorium, in front of all their employees, with a little verbal abuse to carry them out the door? No real stock price advantage to it, just cruelty. Which is exactly what Jobs did to the creator of MobileMe, asking the crowd, “Can anyone tell me what MobileMe is supposed to do?” and following their response with, “Then why the fuck doesn’t it do that” before delivering the public dismissal/blood sacrifice.

2 Elon Musk

Fifty-two-year-old memelord Elon Musk is a common target on this website, and of mine. Water-carriers will imply that this makes me a hater and/or an estrogen-flooded soy enjoyer, which is just fine by me. If he wants to continue to slam his forehead against the glass of the internet humor sphere by posting funny pictures that are two JPEG artifacts away from a Facebook Minion meme, I’ll continue to run his pants up the online flagpole.

Before we go further, let me reiterate that the man is 52. I want to make sure that information is adequately suffused through both paragraphs. With that in mind, the man has made it his nonstop mission to prove that he has the personal skills of a 13-year-old refusing to process their parents’ divorce. It turns out that his desperate need to be considered funny, one that would have simply left him some niche internet forum’s problem if not for his bankroll, frequently spills over into his business. Most laughably, this resulted in him reportedly firing a Twitter engineer who explained that his tweets weren’t getting very many impressions because people didn’t find them particularly interesting.

1 Dan Snyder

Possibly the only person who can hold a candle to Elon Musk’s professional pettiness is a man I am unfortunately thoroughly familiar with as a D.C. native. That is, of course, the thankfully no longer owner of the Washington Commanders nee Football Team nee Native American Slurs, Daniel Snyder. A despicable sort of man who sat back and watched his fortune grow by owning perhaps the most effort-free ticket to increasing wealth — a professional football team, one he originally purchased with the proceeds of a communications company that it turned out might not have been based on sterling business practices in the first place.

Whatever he was the head of, his life is a low-stakes rampage against anyone he believes has wronged him. The Washington City Paper outlined a literal alphabet of petty offenses made by Snyder, an article he quickly settled any doubts about by suing them over. A couple of his greatest hits: He allegedly threatened to send a flat-screen TV to receiver Laveranues Coles’ home after Coles refused to give up a contractual bonus to facilitate a trade, telling him he’d be “better off watching the games there.” He sued a 72-year-old grandmother when she couldn’t pay for her season tickets because of the 2008 housing crisis. A local favorite tale was when Snyder, a man who, let it be clear, has never coached football on any level, reportedly decided to let defensive coordinator Mike Nolan know he thought his schemes were “too vanilla” by repeatedly leaving tubs of vanilla ice cream to melt on his desk.

Eli Yudin is a stand-up comedian in Brooklyn. You can follow him on Twitter and Instagram at @eliyudin and listen to his podcast, What A Time to Be Alive, about the five weirdest news stories of the week, on Apple Podcasts, Spotify or wherever else you get your podcasts.