Why Are All the Billionaires Around Trump Such Losers?
May 5, 2025
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To the extent that the various creeps surrounding Mad King Donald have a coherent program of social change, it looks something like this: 1) Decapitate the institutions of elite American culture, 2) install skeezy billionaire apparatchiks to lead them, and 3) wait for American life to be transformed in their own image.
Substantial philosophical backing exists for this theory of change. The belief that a relatively narrow class of intellectuals manages the social order—and that their worldview trickles down through the rest of society—can be found lurking in the writings of 19th-century capitalist James Mill, 20th-century Marxist Antonio Gramsci, and neoliberal icon Friedrich Hayek, to name just three.
Instead of the populist revolution described by contemporary conservative commentators like Batya Ungar-Sargon and Sohrab Ahmari, the billionaires who’ve attached themselves to Trump basically want to swap one group of cultural elites for another, and they see politics as their way in. Many of today’s elite institutions are weak (Columbia University, lol) and integrated in various ways with the federal government. Through (frequently illegal) funding cuts and mass layoffs, Trump and Elon Musk are not so much shrinking government as weakening cultural institutions to allow for an easier leadership swap.
Silicon Valley billionaires just figured out that their own thirst for power can sound pretty populist if you yell about elite failures and mumble about your plan to do something about it. But where populists want to level inequalities between the rich and the rest, the Trump creeps just want to be the guy sitting in the fancy chair telling everyone what to do.
The situation is grim, the dangerous phase is only beginning, and a great many people will be hurt before things improve. But in the meantime, the Trump brigade is testing a genuinely fascinating philosophical problem: Can you hijack a nation’s culture with a crew made up entirely of losers?
Just look at these guys! Never has so much money surrounded so little rizz. Jeff Bezos, the world’s most prosperous shopkeeper, has been living out a painfully predictable midlife crisis for the better part of a decade. After cheating on his wife with a washed-up local TV anchor (also married), he divorced the mother of his children, lifted a bunch of weights, and designed a spaceship that looks like a penis.
I want to emphasize that last part. Spaceships are almost definitionally cool, and—it’s OK to admit it—everybody enjoys a good dick joke now and then. This should be a pretty safe place to start upping your cultural influence, a comfortable buy-game early in the season. And yet the hilariously lame Blue Origin Flight 11 demonstrates that Bezos has instead achieved the extraordinary feat of making space travel uncool. Sending his fiancée to space with Katy Perry on the latest Blue Origin flight sealed the deal. Instead of showing everyone how cool they all were by associating themselves with space travel, they generated an entire theater of public discussion about how antisocial the whole thing was. Look at little earth, and all the little people! And look at us! We are so rich!
It’s not just space. Tell the muscular men in your life that they look like Jeff Bezos and see how it goes. Or talk to someone who works at the Washington Post, a place that definitely used to be cool. The Pentagon Papers, Woodward and Bernstein—very cool. Bezos, alas, has so thoroughly tainted the place with his anti-rizz that the Post can’t find anyone willing to serve as editor in chief—once among the most prestigious and still one of the most lucrative jobs in American journalism. The institution is decapitated, and now nobody wants it.
The intellectual point here is that it’s hard to sell things that nobody wants to buy, even when you’re running the show. Elon Musk, Peter Thiel, Jeff Bezos, and Mark Zuckerberg can manipulate our intellectually compromised president all they want with gazillion-dollar parties and dark money maneuvers, but what does their vision for the future actually look like? Does anyone want to live there?
Mark Zuckerberg used to run a company called Facebook, until it became so uncool that he had to change its name to Meta. The company began as a clone of various social media sites floating around post-Y2k, made distinct by the deliberate application of Ivy League exclusivity. Facebook was initially a very special Friendster for Harvard students only, a circle which then widened to the Ivy Leagues, then to fancy public universities, and eventually to everybody. But the original reason to log onto Facebook was that it offered you the chance to participate in something Harvardish. It’s an example of cultural transformation from the top, in which people eager for their own piece of exclusivity get their information from a platform managed by Harvardians, and help Harvardism spread through digital life.
If you believe The Social Network—Zuckerberg has said the movie “made up stuff that was hurtful”—he didn’t even come up with the Ivy League–exclusivity trick himself. That was the brainchild of the Winklevoss twins, billionaires who spend their free time covering Journey and Sublime songs (Iame!). Soon after Zuck won a legal battle with the Winklevii over who really created Facebook, he went on an impressive losing streak.
He famously blew $100 million trying to revamp Newark, New Jersey’s public schools, only to get a bunch of schools closed. Blindsided by Instagram, Snapchat, and TikTok, Zuck responded by purchasing Instagram and turning it into TikTok. He lined up a ton of corporate sponsors to go in with him on a massive crypto project called Libra, but the whole thing crashed before launch. (The Winklevii, by contrast, did eventually get rich on crypto.) Zuck then spent more than $20 billionessentially trying to turn Zoom meetings into cartoons. It was called “the metaverse,” and everyone has forgotten about it because it never happened. He then went to war with Apple in the race to corner the market for face-mounted video game consoles. Now he’s into creating A.I. friends for lonely people. Nothing screams digital cool like fake robot friends.
You can go on like this with just about everybody lining up to line Trump’s pockets these days, but we will conclude with perhaps the most reviled man in America, Elon Musk, the richest loser in history. After being forced out at PayPal by Peter Thiel, Musk invested in an electric vehicle startup called Tesla and pushed out both of its co-founders.
Tesla has always been more story than substance—the vehicles are technologically obsolete overseas—and his vast personal fortune is largely the product of stock market hype and accounting quirks. Over the course of 2020, Tesla became a wildly overvalued company, its stock surging from $86 a share to $650, much of which was a result of the technical operations of index funds. When Tesla was listed in the S&P 500 during the pandemic, every investor with money in the index fund found themselves automatically purchasing a lot of Tesla stock. The company’s price rose 33 percent on the announcement that it would be listed in the S&P 500 alone. Musk’s net worth skyrocketed, and he moved on to converting Twitter into a playground for Nazis.
Aristotle tells us that the man who is beyond society is either a beast or a god. But the 21st century has revealed a third option: the loser oligarch. To be a billionaire is to enjoy wealth so vast that you cannot identify with the other humans around you, to cycle between craving the approval of a public you can no longer understand and contempt for that same public that does not approve. At a New York Times event 18 months ago, Musk insisted that “it’s a weakness to want to be liked.” He would know.
According to Trump administration insiders who spoke to Rolling Stone, Musk is “annoying,” not funny, and desperate to be funny—a description that clicks for anyone who remembers him ruining a Dave Chappelle show two years ago. “Elon just thinks he’s smarter than everyone else in the room and acts like it, even when it’s clear he doesn’t know what he’s talking about,” one insider told the magazine. He is not a futuretech visionary, he is a failed clown.
Sometimes these guys do have a certain weird charm. Sam Bankman-Fried convinced a lot of people that he was a major economy-technology brainiac by skipping haircuts and insulting the concept of books. A lot of people really wanted to eat that up! But not forever.
That’s the dirty secret about the Silicon Valley guys: They have become outsiders to society, but they have always been embedded in elite culture. They’re the Ivy Leaguers who made the most money off the internet, the central clearinghouse of 21st-century culture. They’re not replacing the current slate of corrupt elites—they are the corrupt elites, and everyone hates the world they’ve made. They didn’t know what they were assembling when they put together their digital monstrosities, and they can’t fix what they made because they don’t even know what it’s for. But deluded by the aura of wealth, aggrieved social conservatives have turned to the very people who built the digital culture nobody likes—the vast, godless, isolating, stress-inducing, pornographic juggernaut—to win back social prestige for faith and family.
“A lot of these technologists hoped that the centrist path was a viable one, because it would permit them in theory to change the culture without having to expose themselves to the risk of becoming partisans,” far-right social conservative political operative Chris Rufo told Semafor. Now, he insists, “the smartest people in tech” have become “explicitly political” and pro-Trump.
It’s an outrageous joke in every direction. Whatever else these guys might do, they can’t make what they’re doing cool. Just ask Katy Perry.
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