Outsight Book Reader Diary

United States of Oligarchy: How America's Wealthiest Ally with Dictators, Weaken the U.S., and Destroy Democracy by Casey Michel
My rating: 4 of 5 stars

This richly detailed and thoroughly researched investigation paints a picture of the MAGA-era American oligarchs as Lex Luthor-like mega-villains. Consider the Trump dreams of Greenland and the oligarchs' fever dream of Praxis, a proposed city to which they can repair for global dominion.

This mess of power-mad techno-bros was enabled when Justice Anthony Kennedy authored the landmark 5-4 majority opinion in the 2010 Citizens United v. FEC decision, which ruled that the First Amendment prohibits the government from restricting independent political expenditures by corporations, labor unions, and other associations. In his opinion, Justice Kennedy argued that political speech is indispensable to a democracy and that the First Amendment does not allow Congress to limit this speech based on the speaker's corporate identity.

• Money as Speech: The court determined that political spending is a form of protected speech, meaning restrictions on independent expenditures equate to limiting free expression.
• Defining Corruption: Kennedy’s opinion narrowed the definition of corruption, stating that only quid pro quo corruption (direct exchanges of money for political favors) justified limiting political participation. Independent spending, he argued, does not inherently lead to corruption.
• The Marketplace of Ideas: Kennedy famously stated that "there is no such thing as too much speech". He maintained that the government cannot level the electoral playing field by silencing certain voices, but should instead let citizens evaluate messages in the marketplace of ideas. [1, 4]

To balance the ruling's allowance of unlimited independent spending, Kennedy relied heavily on the promise of transparency. He argued that instant, real-time disclosure of election spending over the internet would allow shareholders and voters to hold organizations accountable.
However, this assumption has been widely debated. The proliferation of "dark money"—where funds are channeled through non-profit organizations that are not legally required to disclose their donors—has largely obstructed the accountability and transparency that Justice Kennedy anticipated. Critics, and even some proponents of the ruling, argue that the expected transparency failed to materialize in the way he envisioned. Some of the analysis of the Kennedy opinion in this book:

...in perhaps the most myopic line written in the entire history of the Supreme Court, “The appearance of influence or access will not cause the electorate to lose faith in our democracy.” It was all a jumble of contradiction, a confused mess of sloppy logic and sloppier history. As analyst Matt Ford wrote, Kennedy’s reasoning was “a stark and somewhat blasphemous vision for the American republic.” Rather than an electorate of informed citizenry and republican virtue, Kennedy claimed that the constitutional framers had outlined a nation of pure transactionalism— one in which money would buy political favor, and vice versa.

So from the Kennedy-delivered Super PACs money gave birth to power which corrupted and engendered the monsters of corruption: the oligarchs. And where are we now with the skewed wealth? Frontmatter statistics:

Years in which the bottom 90 percent of America owned more than the top 1 percent: 1946– 2005
First year the four hundred richest Americans paid a lower tax rate than the bottom 50 percent of Americans: 2018

We are treated here to the evolution of the idea of and warning against oligarchism from classical Greece to American history:

Surveying the ruling class in Athens, Aristotle decided that the literal definition of oligarchy was too pat. To the philosopher, oligarchy was something more, beyond mere numbers and power. It was better understood as a system in which “men of property have the government in their hands.”

...

As Aristotle saw it, you could also define oligarchy by what it wasn’t. To Aristotle, the antithesis of oligarchy was clear: democracy. As the philosopher continued, “Democracy [is] the opposite, when the indigent, and not the men of property, are the rulers.” And yet, even then, Aristotle wasn’t finished. 40 The philosopher concluded that it wasn’t simply the number of rulers, or the acreage of property ownership, that defines an oligarchy. Rather, it was wealth— the amount of wealth associated with the oligarchs

...

The Founders “feared a . . . source of power that could damage their grand experiment in popular government: extraordinarily rich Americans whose aims did not align with democracy,” scholar George Thomas noted. 60 One early American official, Gouverneur Morris, worried that “the schemes of the rich” would take advantage of the passions of the people, resulting in “a violent aristocracy, or a more violent despotism.” As Morris described, oligarchic wealth “tends to corrupt the mind and to nourish its love of power, and to stimulate it to oppression.”

...

Sumner railed against the “slave oligarchy” trying to make the entirety of North America— and potentially far more— safe for slavery. “All who seek purity in the National Government must unite in this purpose,” Sumner thundered, “for only by the overthrow of this corrupt oligarchy, which, beginning in the denial of all human rights, necessarily shows itself in barbarism and corruption of all kinds, can a better order of things prevail.” For Sumner, the rise of an “Oligarchical Combination of slave masters, unknown to the Constitution, never anticipated by its founders, and existing in defiance of their example, has entered into and possessed the National Government, like an Evil Spirit.”

Hawaii is explored in depth as a case of the full range and impact of an American oligarchy

Lili‘uokalani’s oligarchic opponents whined that her proposals “reduced white influence”— a reality they would do everything, and use as many tools as possible, to oppose. But it wasn’t just opposition. As Dole’s lone biographer described, the oligarch and his coconspirators “began a campaign of attack upon every part of the [Hawaiian] government.”

...

Pushing through yet another constitution in 1894, these oligarchs restricted voting even further, limiting it to only the wealthiest, most propertied— and, needless to say, white— residents, with well over 90 percent of the islands now unable to have any say in the country’s politics. In the oligarchs’ minds, “The Hawaiians . . . and any other non-Teutonic members must be prevented from voting.” It was the equivalent of the mainland’s Jim Crow regime, set in the middle of the Pacific. 118 But it wasn’t just the voting restrictions. Any residual evidence of Hawaiian nationality— language, culture, identity— would have to be eliminated. As Helena Allen, who authored the only biography of Dole, wrote, “The Republic— an oligarchy— saw the last remnants of Hawaiian culture being changed.

...

With the final ascent of the oligarchy, Hawaii had effectively collapsed into a white supremacist police state. Any dissent, any opposition, any criticism would not be brooked.

I have a tendency to thank of Teddy Roosevelt as a macho racist proto-MAGA type. Here his more circumspect and progressive side is explored.

...he called for Americans to do everything they could to thwart a “civilization of a mere plutocracy.” It was a world that Roosevelt recognized intimately, given his upbringing. The “plutocrats”— the term Roosevelt used to describe the oligarchs— had already created a nation of “selfishness so appalling” that it could, if unchecked, usher in a “destruction hitherto unequaled.” It was language that seemed lifted from the socialists burgeoning throughout the era, but came from the mouth of a president attached to greater wealth than perhaps any before.

Some of the international reach and motivation of profiled oligarchs, like Zuck

...telling his staff that “everyone need[ ed] to tackle this intensively right away, if Facebook’s going to get into China anytime soon.” To that end, Zuckerberg laid out a three-year plan to have Facebook “fully operational” in China, from opening a sales office to partnering with a “senior Chinese leader” in order to build out a formal “partnership” with the Chinese government.

...and wannabe statesman Kushner

...even as a key player in the Trump administration, Kushner still had that albatross slung around his neck: that skyscraper at 666 Fifth Avenue, dragging Kushner’s corporate wealth like an anchor, down into the deepest red. There had been one moment, right before the election, when Kushner thought he’d found a lifeline. Joining his father, Kushner sought out a half-billion-dollar investment in the building from a leading figure in another Middle Eastern nation: Qatar. Connecting with Sheikh Hamad bin Jassim al-Thani, the former head of Qatar’s sovereign wealth fund (and a man also known by his own initials, HBJ), the Kushners thought they’d initially found success, with HBJ pledging $ 500 million on the condition that the Kushners could raise the rest of the needed financing elsewhere. Negotiations bled into 2017, well into the new Trump era— an era in which Jared Kushner was suddenly America’s chief diplomat, in practice if not in name. However, after revelations about a number of other potential investors in the building sparked public criticism, the Qataris pulled out— leaving the Kushners once more on the hook for spiraling debt payments. And then, the blockade began. In early June 2017, the Saudis, Emiratis, and a number of other regional regimes severed both diplomatic and economic ties with Qatar. Invasion hung in the air, with Saudi and Emirati troops massing across Qatar’s border. A tinderbox looked set to explode. Even more shocking than the blockade, however, was Washington’s response. Rather than act as the neutral arbiter many expected, the Trump administration immediately threw its weight behind the Saudi and Emirati moves— a stance led by none other than Kushner, who, according to CNN journalist Vicky Ward, “greenlit” the entire operation in the first place. “The Saudis would not have risked moving forward without permission from somebody,” one Tillerson aide said. The conclusion was inescapable: “That person must have been Jared.”

...

MBS knew, Kushner was a man who, if the political winds in America blew in a slightly different direction, could help take the Gulf tyrant to ever-greater heights. The Saudi panel screening investments advised against partnering with Affinity and Kushner. But MBS immediately overruled them. Kushner and Affinity would get Saudi funding— $ 2 billion to start, and potentially much more down the road. And MBS would once more have a partner in the US who he could steer in whichever direction he wanted.

...
Kushner’s influence has not only continued during Trump’s second term, but is arguably more impactful than ever. As Reuters reported in early 2025, Kushner “remains involved behind the scenes,” including by “advising on Trump’s Middle Eastern strategy, helping select appointees and guiding certain cabinet members through the transition.” 824 Specifically, Kushner is “very, very close” to Trump’s chief of staff, Susie Wiles, speaking to her “regularly.” 825 All told, according to Trump biographer Michael Wolff, Kushner has a “hidden hand” in Trump’s second administration— one you can see shadows and hints of, but one that hasn’t seen nearly enough attention, or nearly enough investigation. 826 Perhaps most pertinent, Kushner has been a direct adviser to the man who replaced him as the head of the Middle Eastern portfolio

Then, these network globally:

No one had forced figures like Bezos, Zuckerberg, or Pichai to build out their own links with tyrants around the world, gutting their pretenses about supporting liberal democracy...

The author also directly explored the bizarre Putinist-Far Right connection:

I’d arrived in Moldova to report on the annual conference of the World Congress of Families (WCF). The WCF was itself the foremost fundamentalist group anywhere in the world: a transnational organization dedicated to rolling back as many of the basic elements of liberal society— abortion access, same-sex marriage, even individual rights writ large— that it could find. It was, then as now, the leading bridge between hard-right American Evangelicals and fundamentalist counterparts in Russia, receiving funding from oligarchs on both sides

...

“Putin is an imperialist,” he said, wiping his mouth. “But what’s worse: Imperialism, which will kill your body, or the gender ideologies that the [West] pushes, which will kill your soul?”

...

He is also one of Russia’s most notorious oligarchs, a billionaire henchman for Putin, dedicated to obliterating democracy wherever and however he can, whether in Russia or elsewhere. Malofeev was one of the key figures behind Russia’s initial invasion of Ukraine in 2014, overseeing much of the post-invasion investment in occupied Ukraine— including, memorably, a theme park dedicated to Russian history.

...

The date was January 6, 2021. And the speaker was a man who would later be outed not only as one of the WCF’s recent keynote speakers, but as the author of Trump’s entire strategy to overturn the 2020 election and overthrow American democracy entirely: John Eastman.

...

as Russian journalists later discovered, the starting gun for the Kremlin’s invasion preparation rang out the day Ukraine went after Medvedchuk. “Three sources in the Russian president’s entourage confirmed that it was this story of the destruction of Medvedchuk’s [television channels] and the fact that [Ukraine] began to ‘harass’ him that became the last straw in Putin’s decision to prepare for a military operation,” Russia’s Verstka Media reported. As one of Putin’s acquaintances said, “[ Putin] took it as a personal attack,” viewing it as a Ukrainian escalation against him and his oligarchic proxies.

...

Most spectacular, American Ethane’s ownership group at one point even included Roman Abramovich, perhaps the most successful (and certainly most notorious) Russian oligarch of the bunch— a man who’d not only purchased the Chelsea Football Club, but who slid his illicit wealth into offshore vehicles around the world, slithering into the highest ranks of Western policy and cultural circles in the process.

...

The fact that a supposedly American firm like American Ethane was secretly controlled by a series of Russian oligarchs would have been problematic enough. Yet as with other American corporations, American Ethane had additionally tossed a raft of donations to US politicians far and wide: to the most powerful Republicans in states like Louisiana, to a fund overseen by House Majority Whip Steve Scalise, and even to the reelection campaign of Mike Johnson, who would soon become the Speaker of the House. The donations themselves weren’t titanic, coming in at only five figures, but they effectively illustrated how American corporations could turn into a sieve for foreign funds to drown American politics.

Of course, Musk, too.

Musk didn’t stop there, and quickly slid into outright genocidal apologia. “China’s repression of the Uyghurs,” Musk claimed, “had two sides.” Musk didn’t bother to describe what those “sides” were, or if, for instance, there were also “two sides” to previous genocides like the Holocaust. China may be committing horrific crimes, yes— but, as Musk saw it, perhaps the Uyghurs deserved it? Who were we to judge?

...

in early 2022, Musk immediately swooped in to aid Kyiv’s efforts against Russian troops. Both Musk and Ukrainian officials realized that Starlink— the Musk-led company arranging satellite coverage in far-flung reaches of the world— was perfectly placed to help Ukrainian troops converse across the battlefield. Musk even directly oversaw Starlink’s Ukrainian strategy, convening with company engineers for days on end, outlining ways the company could help circumvent Russian jamming. Soon, thousands of Starlink terminals flooded into Ukraine, with Musk transforming into the most impactful nongovernmental official of the early phases of the war. As one Ukrainian commander said, “Without Starlink, we would have been losing the war.”

...

rolling back Russian troops and proving the futility of such colonial expansion was clearly necessary. Ukraine was on the frontline of the fight for not only tangible topics like territory, but things far airier and far more important like freedom, democracy, and anti-imperialism writ large. For Musk, though, there was something more important yet: Armageddon. At least, that’s what later reporting revealed, trying to parse Musk’s thoughts during late 2022, when his views on the war— and on the rightness of Ukraine’s fight— flipped on their heads. In Musk’s mind, Ukraine’s successful parries against Russia were less signs of strategic success, and more risks that could lead directly to nuclear annihilation. As Ukraine’s pushback continued throughout 2022, Musk went into “crisis-drama mode,” with the oligarch suddenly starting to worry that Ukrainian success— and Starlink’s key role therein— could “lead to a nuclear war.” 698 Musk’s concerns didn’t arise in a vacuum. With his troops smothered and scattered, Putin had also begun rattling a nuclear saber, claiming that further Ukrainian advances would result in Moscow unleashing nuclear warfare on Kyiv...

...
Musk had spent much of the 2020s growing more and more reliant on Tesla’s success in China, both as a source of his personal wealth and his professional standing. To swipe an overused analogy, it was a bit of domino theory in effect: Musk’s political standing relied predominantly on his personal wealth, which relied predominantly on the health of the Tesla shares populating Musk’s portfolio, which relied predominantly on scaling up sales and production in China— all of which relied entirely on remaining in the good graces of Beijing itself. It’s not as if any of this was a secret, necessarily. As a Wall Street Journal headline blared after Trump’s election, China specifically saw Musk as a “conduit” to Trump.

Scholarly debate on the impact of such elitism:

One of the first to tackle the question head-on was Robert Andersen, a sociology professor</a> at the University of Toronto. Surveying dozens of countries, Andersen tried to answer one question: Did economic inequality really have a detrimental effect on democracy?

...democracy— Andersen discovered that “income inequality matters much more.” Overall wealth was still important, but the economic disparity within a country was far more pertinent to that nation’s support for democracy. Democracy, as he wrote, has “less support in countries with high income inequality.” The more unequal a nation, the less the support for democracy, full stop

Other scholars have confirmed as much in the years since. In 2024, South Korean scholar Sang Kyung Lee determined that “where inequality is more severe, citizens in liberal democracies are more attracted to authoritarian leaders.”

And those authoritarians consolidate power:

In 2022, The Washington Post reported that Ellison, who’d long bankrolled Republican politicians and causes, was directly involved with something else: conversations about how Donald Trump and his allies could overturn the 2020 election. It’s unclear what Ellison said regarding Trump’s attempted coup on January 6, 2021. But as The Post reported, Ellison’s participation was “the first known example of a technology industry titan joining powerful figures in conservative politics, media and law to strategize about Trump’s post-loss options.”

Adding it all up, we find there really is a bunch of crazy mega-rich scheming to own the world:

...thanks to Trump, it was a nonstarter. Where FARA had once been the lodestar for foreign lobbying legislation around the world, Bondi announced that it was now effectively dead— and all that information and transparency that Americans once had access to would be no more. 750 In another memo, Bondi declared that the Trump administration was also dissolving another prong of the US’s fight against kleptocracy: the FBI’s Foreign Influence Task Force. First created in 2017— during Trump’s first term, ironically— the group had quickly transformed into the US’s leading tool for tracking and tracing foreign influence campaigns around the country, dedicated to dismantling infiltration campaigns out of places like Russia, China, Iran, Venezuela, and more.

Next on the chopping block was the Kleptocracy Asset Recovery Initiative. Inaugurated in 2010, this was a body dedicated to freezing, seizing, and repatriating assets linked to dirty money networks around the world, who often plowed their illicit wealth directly into the US. While this task force was always fighting an uphill battle— the millions it returned hardly compared to the billions (or more) pilfered around the world— it nonetheless stood as a testament to the US’s public willingness to go after these networks. In Nigeria, in Malaysia, in Uzbekistan—
These are all a jumble of names and acronyms, neologisms unfamiliar to those outside Washington. But pulling back, one thing from Bondi’s memos was clear: In a single day, just a few weeks into Trump’s new administration, the US had eliminated or kneecapped its most successful and most prominent counter-kleptocracy tools. Years of progress had been undone.
Trump simply announced that there was a whole suite of legislation that folks no longer needed to worry about. He had created a new legal architecture by fiat, providing a public road map for as much white-collar crime as crooked regimes and corrupt oligarchs could want. And still, he wasn’t done. While he was busy dismantling legislation, he was also busy creating new ways to attract illicit wealth into the US. One of his new tools was the creation of a so-called “gold card” visa scheme. Sitting in the Oval Office, Trump hawked a “path to citizenship” for anyone who could pay $ 5 million. Anyone— any drug lord, any human rights abuser, any oligarch around the world— who could meet that fee could visit the US, setting them on a path to American citizenship.
Leaving aside all the raging concerns about the world Altman’s ChatGPT has helped create— the rampant copyright violations, the environmental damage, the collapse in students’ abilities to craft their own essays, and more— Altman’s willingness to back Praxis’s vision of a post-nation future raises questions about not only his own political leanings, but about his vision for the future of the United States itself.
According to a number of sources, a range of “Silicon Valley tech investors” have begun “promoting the frozen island as a site for a so-called freedom city, a libertarian utopia with minimal corporate regulation.” Aligning with Praxis’s vision for a network state in Greenland, Reuters reported that these oligarchic investors envisioned transforming Greenland into a paradise of scientific, even utopian, invention, building the island into a “hub for artificial intelligence, autonomous vehicles, space launches,

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