On December 14, 2016, President-elect Donald Trump crammed a handful of America’s most recognizable moguls into a conference room on the 25th floor of his Manhattan headquarters. The group included Amazon’s Jeff Bezos, Tesla’s Elon Musk, and Apple’s Tim Cook. Despite having just won the most powerful position on the planet, Trump assumed a sycophantic pose.
“There’s nobody like you in the world!” Trump exclaimed. “In the world!”
He wanted them to know: “I’m here to help you folks do well.”
At that early date, Trump was a somewhat unknown quantity, at least as far as these billionaires were concerned. They couldn’t be sure if he was actually aligned with their interests, given his support of tariffs, hostility toward immigration, and fulminations against globalism. Besides, it was an especially inflamed moment in American politics, and the executives had reason to fear that their workforces, not to mention their customers, might furiously protest an intimate working relationship with Trump. So after the meeting adjourned, Trump’s offer of an alliance was left dangling.
If Trump prevails on November 5, a version of the partnership he hinted at eight years ago will finally emerge, and in a far more robust form than he could have ever imagined at the time. That’s because many of the wealthiest Americans have reached the cold conclusion that the opportunities presented by Trump outweigh whatever social opprobrium might follow an embrace.
There’s a word for this type of cozy arrangement: oligarchy. The term conjures the corrupt illiberal system that governs Vladimir Putin’s Russia. But like fascism or democracy, the concept varies from country to country, a product of its native political culture and sources of wealth.
The Trumpist oligarchy that is taking shape is far different from the post-Soviet strain. What makes it distinct is that Trump is entering into a partnership with the most powerful technologists in the world. But the core problem of oligarchy is the same. The symbiotic relationship between a corrupt leader and a business elite always entails the trading of favors. The regime does the bidding of the billionaires and, in turn, the billionaires do the bidding of the regime. Power grows ever more concentrated as the owners and the corrupt leaders conspire to protect their mutual hold on it. In short order, this arrangement has the potential to deliver a double blow to the American system: It could undermine capitalism and erode democracy all at once.
Perhaps it will soon be possible to look back on the first Trump term with nostalgia. Back in those days, there was rampant corruption, but it was relatively small-time. Jared Kushner and the Trump kids traded on the family name. In the mix were old friends of the president like Tom Barrack, who allegedly attempted to parlay his presidential friendship to win clients in the Middle East. Supplicants usually ingratiated themselves with Trump by buying units in his buildings and hosting events at his resorts. When the Air-Conditioning, Heating, and Refrigeration Institute wanted the administration’s help, it spent more than $700,000 on an event at a Trump golf resort. In a second term, that brand of blatant transactionalism will reappear, and likely get much worse, because it’s now clear that there are no consequences for engaging in it.
The biggest difference between Trump I and Trump II is that he would return to office at a uniquely perilous moment in the history of American government. Never before has the state been such a lucrative profit center for private business. And not since the Gilded Age has it been so vulnerable to corrupt manipulation.
In part, this is because of a bipartisan shift in ideology. Over the past decade, both political parties have come to embrace what’s called “industrial policy.” That is, to varying degrees, Republicans and Democrats agree that the government should play the role of investment bank, spending billions to subsidize sectors of the economy vital to the national interest—and to protect those domestic firms from foreign competition with tariffs.
At the same time, the federal government has become a massive consumer of technology, in the form of cloud computing and artificial intelligence and rockets, that it can’t efficiently produce itself. From 2019 to 2022, according to a study by Brown University’s Watson Institute for International and Public Affairs, the Pentagon and intelligence community spent at least $53 billion on contracts with Big Technology firms.
All that government spending comes at a time when the bureaucracy that oversees such expenditures is especially precarious. Over the summer, the Supreme Court issued a decision gutting the power of federal agencies. Trump would likely strike another grievous blow against it, extending his power to fire civil servants to purge a tier of experts, lawyers, and clerks hired to be neutral arbiters of the national interest so that he can replace them with his cronies.
Without that accountability, the vast sums the government spends can be more easily funneled to favorite firms; regulation can be more easily manipulated to punish rivals of those firms. Those billionaires with access to the government will have something close to unchallenged control of the economy’s commanding heights.
None of this would exactly resemble Putin’s oligarchy, which largely consists of old chums from the KGB and his childhood friends from St. Petersburg. Russia is an aristocracy of apparatchiks, whose primary goal is to protect ill-gotten wealth amassed during the country’s chaotic transition from communism, a mission that has required brutality and suppression.
But Trump’s and Putin’s oligarchs share one important similarity. The Big Tech billionaires attracted to Trump would hope to protect their monopolies by providing essential services that make them indispensable to the government and the nation. This indispensability will also—so the theory goes—insulate them from antitrust enforcement. It’s far harder to make the case for breaking up a monopoly when that monopoly supplies the Pentagon with communications technologies and runs cloud-computing services for intelligence agencies.
But there’s a distinct twist to the aims of the Big Tech oligarchs: They don’t simply want to insulate themselves from regulators and courts. Ultimately, they want to exploit their relationship with the government in order to supplant it. They want to be the ones who gain control of programs and systems that were once the purview of the state. Their alliance with Trump is, at bottom, a power grab.
Take space exploration. Musk and Bezos don’t just want the government to subsidize their rockets and supply the funds that will further grow their aerospace firms. They want to become the architects of human life in the heavens, to design celestial colonies, to shape the future of space. Then there are the tech billionaires promoting cryptocurrency. They don’t simply want to remove regulatory restraints on the industry. In their vision, their companies will replace the U.S. Treasury. And some of these businesses hope to fend off the regulation of artificial intelligence, so that they can exert more invisible control over the flow of information and commerce.
The central activity of an oligarchical system is the mutual scratching of backs. The head of state helps spread the lucre, but also collects a fee for his services. In Russia and Ukraine, presidents received actual monetary fees in the form of kickbacks. Oligarchs laundered money on their behalf, shifting cash into offshore accounts and buying them ornate villas. In essence, oligarchs serve as errand boys. If they own media, then they use their outlets to subtly make the case for their patron; they hire editors more inclined to spout the party line and to steer coverage in a preferred direction.
It’s hard to imagine transplanting Russian oligarchy to these shores, given the American rule of law and the higher standards of American capitalism. But it’s possible to glimpse how the CEOs have begun to play the game—the way Musk has used X to relentlessly extol Trump, or how Bezos canceled The Washington Post’s endorsement of Harris and hired an alumnus of Rupert Murdoch’s empire to serve as publisher.
Every oligarchical system writes its own informal rules, arriving at its own set of furtive understandings. In contrast to Putin, Trump is aligning with genuinely creative entrepreneurs. Yet that doesn’t make the American model better—just uniquely dangerous. Trump’s transactionalism will be tethered to people driven by greed, but also by messianic fervor, and the result will be like nothing you’ve ever seen.
