At a rally in Las Vegas in September, the reggaeton star Nicky Jam came onstage in a Make America Great Again hat and endorsed Donald Trump. “We need you. We need you back, right? We need you to be the president,” he said. But after a comedian at Trump’s rally at Madison Square Garden last month called Puerto Rico “a floating island of garbage,” the singer—whose father is Puerto Rican and who was raised partly on the island—had second thoughts.

“Never in my life did I think that a month later, a comedian was going to come to criticize my country and speak badly of my country, and therefore, I renounce any support for Donald Trump,” Nicky Jam said.

He had no right to be surprised. Trump himself had previously gone after Puerto Rico—he punished its leaders for criticizing him after Hurricane Maria, and sought to swap it for Greenland—but even if Nicky Jam had missed or forgotten that, he had to know who Trump was.

Nicky Jam was ahead of the curve. Since the election, Trump has moved swiftly to do things he’d said he’d do, and yet many people—especially his own supporters—seem stunned and dismayed. This is absurd. Surprise was perhaps merited in late 2016 and early 2017, when Trump was still an unknown quantity. But after four years as president, culminating in an attempt to erase an election he lost, Trump has demonstrated who he is. Somehow, the delusion of Trump à la carte—take the lib-owning, take the electoral wins, but pass on all of the unsavory stuff—persists.

In an article about how Trump’s transition is “shocking the Washington establishment,” Peter Baker of The New York Times writes: “Nine years after Mr. Trump began upsetting political norms, it may be easy to underestimate just how extraordinary all of this is.” He’s right that the aberrant nature of the picks may be overlooked, as I have warned, yet it is also true that the actual unpredictability of them is overestimated.

[From the January/February 2024 issue: Trump isn’t bluffing]

On K Street, Politico reports, health-care-industry lobbyists can’t believe that Trump has nominated Robert F. Kennedy Jr. to lead the Department of Health and Human Services. They were “expecting a more conventional pick,” even though Trump emphasized Kennedy’s “Make America Healthy Again” agenda late in the campaign, and even though Kennedy said that Trump had promised him control of HHS. To be sure, Kennedy is a shocking and disturbing pick, as Benjamin Mazer and my colleague Yasmin Tayag have recently written for The Atlantic, but his nomination should not come as a surprise—especially for people whose entire business proposition is being highly paid to advise clients on how Washington actually works. (The influence peddlers reportedly hope that senators will block Kennedy. The fact that they’re still waiting for someone else to solve their problems is further evidence of how little they’ve learned, years into the Trump era.)

Meanwhile, the New York Post, a key pillar of Rupert Murdoch’s right-wing media juggernaut, is similarly jittery about the Kennedy choice. Back when Kennedy was a thorn in President Joe Biden’s side, threatening to run against him in the Democratic primary, the Post’s editorial board was all too happy to elevate him. Now the board condemns his nomination and tells us that it came out of a meeting with him last year “thinking he’s nuts on a lot of fronts.” The columnist Michael Godwin, who beamed on November 9 that Trump’s victory “offers the promise of progress on so many fronts that it already feels like Morning in America again,” was back a week later to complain that “it’s not a close call to say” that Kennedy and Matt Gaetz, Trump’s pick for attorney general, are “unfit” for the roles.

The lobbyists and editorialists are in good company, or at least in some sort of company. On Capitol Hill, Republican senators say they are shocked by many of Trump’s Cabinet picks. Senator Susan Collins of Maine, who notoriously professed surprise when Justices Neil Gorsuch and Brett Kavanaugh voted to overturn Roe v. Wade, is “shocked” at the Gaetz nomination. Gaetz’s House Republican colleagues are “stunned and disgusted.”

Reactions to Pete Hegseth’s nomination as secretary of defense are less vitriolic, if no less baffled. “Wow,” Senator Lisa Murkowski of Alaska told NBC. “I’m just surprised, because the names that I’ve heard for secretary of defense have not included him.” Senator Bill Cassidy of Louisiana was even blunter. “Who?” he said. “I just don’t know anything about him.”

[David A. Graham: The Trump believability gap]

If this is true, the senators could perhaps do with some better staff work. Hegseth was a real possibility to lead the Department of Veterans Affairs in the first Trump administration; more to the point, he was a prominent figure on Fox News, which is a dominant force in the Republican Party, from whose ranks Trump has repeatedly drawn appointees.

Staffers at the affected agencies have also expressed shock and horror at the prospect of an Attorney General Gaetz, a Defense Secretary Hegseth, or a Director of National Intelligence Tulsi Gabbard.

Ordinary Americans may also be taken aback. As I reported last month, Trump critics were concerned about a “believability gap,” in which voters opposed some of Trump’s big policy ideas, sometimes quite strongly, but just didn’t trust that he would really do those things. Although they perhaps deserve more grace than the Republican officials and power brokers who are astonished, they also had ample warning about who Trump is and how he’d govern.

Throughout his presidential campaign, Trump vowed to deport undocumented immigrants en masse. He’s appointing officials such as Stephen Miller and Tom Homan who are committed to that, and yesterday morning, Trump confirmed on Truth Social a report that he would declare a national emergency and use the military to conduct mass deportations. And yet, when the roundups start in January, many people are somehow going to be taken by surprise.

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.

[Read: What Elon Musk really wants]

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.

[Read: Jeff Bezos is blaming the victim]

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.