A LABOR DAY LOOK AT TRUMP'S OLIGARCHY
Picture this: it’s Labor Day, a time to fire up the grill, crack open a cold one, and celebrate the backbone of America—the workers who keep the country humming. But in Chicago, the vibe’s less “hot dogs and apple pie” and more “pitchforks and protest signs.” The Windy City’s Labor Day rally, dubbed “Workers Over Billionaires,” isn’t just a catchy slogan; it’s a battle cry against what many see as a creeping, gilded menace: an oligarchy, headlined by Donald Trump’s billionaire-packed administration, that’s threatening to turn democracy into a VIP lounge for the ultra-rich. So, grab a seat (preferably not one at Trump’s cabinet table), and let’s unpack this oligarchic circus, its historical roots, its global cousins, and why it’s got workers from Chicago to Guam ready to march.
What’s an Oligarchy, Anyway?
An oligarchy, for those who skipped Civics 101, is when a small, elite group—usually dripping with wealth, power, or both—calls the shots in a government. Think of it as a country club where the entry fee is a billion dollars and the dress code is “influence peddling.” It’s not just rich people existing; it’s rich people running the show, bending policy to their will, and treating the rest of us like the help. The term comes from the Greek “oligos” (few) and “arkhein” (to rule), and it’s been a political boogeyman since Aristotle griped about it in ancient Athens. Today, it’s less about togas and more about tailored suits and Super PACs.
Oligarchies aren’t just a theoretical vibe. They thrive where wealth concentrates and democratic guardrails weaken. Russia’s a textbook case: post-Soviet privatization turned a handful of insiders into billionaires who now cozy up to the Kremlin, shaping policy to keep their yachts afloat. Think Vladimir Putin’s pals like Roman Abramovich, who parlayed state assets into oligarchic empires. In Saudi Arabia, the royal family and their billionaire buddies control oil wealth and political power, with dissenters politely invited to disappear. Even China’s hybrid system has its princelings and tycoons who blur the line between business and government. Historically, oligarchies have popped up everywhere from Renaissance Venice, where merchant families ran the city like a corporate boardroom, to the Gilded Age U.S., where robber barons like Rockefeller and Carnegie held sway over politics with wallets bigger than their egos.
Trump’s Billionaire Bonanza: The Awful Oligarchy
Fast-forward to 2025, and America’s staring down its own oligarchic moment. Donald Trump’s second term has ushered in what critics call the wealthiest administration in U.S. history, with at least 13 billionaires tapped for key roles, their combined net worth topping $460 billion. That’s not pocket change; it’s enough to buy a small country or, apparently, a cabinet seat. These aren’t just rich folks with opinions; they’re donors, allies, and insiders who’ve funneled millions into Trump’s 2024 campaign, raising eyebrows about whether democracy’s been swapped for a pay-to-play system. As The New Republic put it, “The far bigger menace is the monstrous growth in wealth concentration over five decades that made a Trump presidency possible—and maybe inevitable.Who are these gilded players? Let’s meet the starting lineup of Trump’s “Awful Oligarchy,” a baker’s dozen of billionaires who’ve traded campaign checks for cabinet clout:
1.Elon Musk ($400B+ net worth): The Tesla and SpaceX czar, now chairing the Department of Government Efficiency (DOGE), pumped over $130M into Trump’s campaign, including $119M through his America PAC. Musk’s slashing federal spending with the zeal of a kid with a new chainsaw, but his government contracts raise conflict-of-interest flags.
2. Vivek Ramaswamy ($1B+): The biotech bro-turned-MAGA star co-heads DOGE with Musk. He loaned his 2024 campaign $26M, so he’s no stranger to buying influence.
3. Linda McMahon ($3B+ via her husband): The ex-WWE exec, now Education Secretary, donated $16M to Trump’s cause. Her agency’s on the GOP’s chopping block, which is awkward.
4. Howard Lutnick ($1.5B): The Cantor Fitzgerald CEO, tapped for Commerce, gave $14M. He’s poised to lead Trump’s trade wars, which could fatten his financial empire.
5. Charles Kushner (est. $1B+): Trump’s pick for Ambassador to France, this real estate mogul’s got a rap sheet (pardoned by Trump) and deep ties to the Trump family.
6. Jared Isaacman (est. $1B+): The private spaceflight pioneer, now NASA administrator, brings his SpaceX connections to the table, aligning with Trump’s privatization push.
7. Doug Burgum ($1.1B): The North Dakota governor, now Interior Secretary, made his fortune in software and is tasked with “Drill, baby, drill.”[]
8. Mehmet Oz (est. $100M+): Dr. Oz, of TV fame, joins as a health policy advisor, though his wealth pales next to the heavy hitters.[]
9. Scott Bessent (est. $1B): Nominated for Treasury, this hedge fund titan’s ready to steer fiscal policy toward tax cuts for the rich.
10. David Sacks ($1B+): The PayPal Mafia member, now in a tech advisory role, hosted Trump on his podcast and brings Silicon Valley swagger.
11. Others include lesser-known billionaires like John Catsimatidis, Bernie Marcus, and Woody Johnson, each with their own slice of influence and Trump loyalty.
Then there’s the “Terrible Ten” among the 26 billionaire donors who shelled out over $1M each to get Trump elected, per Forbes. Timothy Mellon ($76.5M) leads the pack, followed by Miriam Adelson ($5.8M, with plans for up to $90M), Diane Hendricks ($6.3M), and Harold Hamm ($5M+). Others like the Uihleins, Charles Koch, and the Wilks brothers round out a roster that reads like a Forbes 400 reunion. Their industries—oil, casinos, finance, real estate—scream “old money meets new hustle,” and their donations scream “we expect a return.”
What Do They Want?
So, what’s the endgame for these billionaires? It’s not just about photo ops at Mar-a-Lago. These donors and appointees are eyeing policies that fatten their wallets and cement their power. Musk wants deregulation for his empire of Tesla, SpaceX, and X, plus juicy government contracts. Hamm and the Wilks brothers are all-in on fossil fuels, cheering Trump’s “drill everywhere” mantra. Adelson’s pushing for pro-Israel policies, like moving the U.S. embassy to Jerusalem (achieved in Trump’s first term). McMahon and Lutnick want tax cuts and a gutted federal government, freeing up markets for their businesses. The throughline? Less oversight, lower taxes, and a government that bends to their bottom line. As David Sirota told Democracy Now!, “These people are not giving money simply out of the goodness of their hearts. They want things. They have policy demands.”
This isn’t just about policy; it’s about power. The Citizens United decision (2010) unleashed a flood of dark money, letting billionaires like these buy influence without breaking a sweat. Super PACs and 501(c)(4)s became their playground, with 99.1% of 2024’s super PAC cash coming from the top 1% of donors. Trump’s campaign leaned hard on this, with 44% of his funds from just 10 donors. It’s not democracy; it’s an auction.
The Historical Echoes
This isn’t America’s first brush with oligarchy. The Gilded Age saw tycoons like Andrew Mellon—who, fun fact, used the IRS to kneecap rivals—wield outsized influence. His grandson Timothy Mellon’s $76.5M for Trump shows the family’s still at it. The 1920s tax cuts let fortunes like Mellon’s balloon, much like Trump’s 2017 tax cuts doubled billionaire wealth to $6 trillion while the bottom half of Americans scraped by. Back then, workers fought back with unions and strikes; today, it’s protests like Chicago’s.
Globally, history’s littered with oligarchic cautionary tales. Rome’s late Republic saw wealthy senators and generals like Crassus buy loyalty and power, paving the way for autocracy. Russia’s 1990s “loans-for-sh
These 26 Billionaires Have Each Given More Than $1 Million to Elect Trump https://www.forbes.com/sites/leokamin/2024/08/14/here-are-trumps-top-billionaire-donors/
Trump has tapped an unprecedented 13 billionaires for his administration. Here's who they are - ABC News https://abcnews.go.com/US/trump-tapped-unprecedented-13-billionaires-top-administration-roles/story?id=116872968
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Trump's planned assault on Chicago. Remembering the Ft. Hood 43 who refused to march on Chicago in '68. https://michaelklonsky.substack.com/p/trumps-planned-assault-on-chicago
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