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The Deal With the Devil that Paved the Way for Trump’s Oligarchy

As Donald Trump prepares to usher in an oligarchic dark age, Democrats must reflect on how their own flirtation with plutocracy shattered their party’s chances

Billionaire businessman Mark Cuban arrives to speak at a campaign rally for Democratic presidential nominee Vice President Kamala Harris. Photo: Associated Press / Alamy

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If there was ever a moment that heralded America’s transition towards oligarchy, it was the 2010 Citizens United decision.

The Supreme Court’s decision opened the floodgates to billions of dollars in opaque funding flooding US politics and drowning out the already dwindling decision-making power of regular Americans. For the last several election cycles that have followed, we’ve watched as secretive plutocrats, special interest groups, and multinational corporations held sway in the dark. 

But in the 2024 election, for the first time, they didn’t even try to hide it. 

Elon Musk, the world’s richest man, spent hundreds of millions of dollars on the Trump campaign, even offering $1 million a day to swing-state voters. Somehow, absurdly, that was judged to be legal. Despite the fact that he’s a major recipient of federal contracts, Musk has been openly rewarded with a high-profile advisory role on restructuring the federal budget. At a certain point, it ceases to be merely a conflict of interest. It becomes oligarchy.

Another mega-billionaire Trump donor, Miriam Adelson, reportedly conditioned her generous donations on foreign policy commitments. She wanted support for an illegal Israeli annexation of the West Bank. It looks likely she’ll get what she paid for. Other donations, from bankers, asset-managers like Blackstone and Blackrock, tobacco companies, the fossil fuel industry and others, are highly likely to have strings attached. 

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But Democrats, too, have had their priorities warped by oligarchic influence. One of Harris’ key inner circle campaign advisors (and her brother-in-law) was Uber executive Tony West. West successfully urged the campaign to ditch early messaging attacking big business and Wall Street for their greed. The greed which we now know, empirically, is linked to inflation, because he was trying to court technology and finance magnates to the cause. 

Per West’s advice, in came the “cool” billionaire surrogates. One such campaigner, Mark Cuban, publicly bragged that he had played a role in axing a Harris spokeswoman for the cardinal sin of supporting a wealth tax. A tax that, of course, he would have had to pay. 

Others waged an internal war on the Biden administration’s Federal Trade Commission (FTC). Lina Khan, progressive darling and Gen-Z’s beloved FTC head, has led on an antitrust crusade in America since 2021. Under her tenure, the FTC has used long-ignored antitrust laws to fight corporate consolidation, protect consumers from illegal activity and corporate abuse, and take big tech companies to task. 

At the time, Nicole Gill, Co-Founder and Executive Director of Accountable Tech, emphasised to Byline Times the crucial role Lina Khan was playing in the battle against online disinformation: 

“Lina Khan has proved to be a powerhouse, taking on Big Tech monopolies while corporate accountability measures have stalled in Congress. She has used the tools at her disposal to take action, while legislators have struggled to keep up with the latest threats posed by the industry – making her a key figure at the federal level to ensure we are keeping Big Tech’s power in check. Khan’s continued tenure at the FTC is crucial not only to break up Big Tech’s undue power and influence over our lives, but to the antitrust movement writ large.”

But for mega-donors and fundraising surrogates including Reid Hoffman and Barry Diller, Khan’s FTC was bad for business. Hoffman attacked Khan directly, calling her “a person who is not helping America.” Despite his claim to separate his expert advice from his role as a political donor, Hoffman sits on the board of Microsoft – a corporation actively under litigation from the FTC. Diller, who called Khan a “dope,” was also facing multiple FTC investigations into his holding company, IAC. 

Cuban, Hoffman and Diller are not Elon Musks. Their influence is far less consequential, and as far as we are aware they were not promised Government posts. But in an election that was fundamentally a referendum on the status quo, it signalled that no party in America was willing to go after big business or billionaires. Despite electing Trump, resolving entrenched inequality is something all Americans, inluding Republicans, care deeply about.

More fundamentally, these decisions locked the Democratic base – the regular people – out of the campaign. As New York Times reporter Astead Herndon, who spent months on the campaign trail, put it: “Republicans work from the premise of supporting and appeasing their base, and making the rest of their people go along with it. Democrats don’t work from that premise. They work from appeasing the others and making their base go along with it.”

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The result is that “they just blocked people out.” Herndon offers his advice: “If you make decisions removed from the public, at some point, that’s going to catch up to you. This is still a thing that is driven from the bottom-up.”

Usamah Andrabi, Communications Director of the Justice Democrats –a campaign group dedicated to campaign finance reform, ending billionaire politics, and electing working-class Democrats, including Alexandria Ocasio-Cortez and others – agrees with that diagnosis. 

“What we are seeing right now is a Democratic party that runs top down, both from its leadership as well as from a class perspective,” Andrabi told Byline Times. This election saw a particular lack of internal party democracy, given the short time frame after Biden’s withdrawal and the lack of a primary contest. 

“I think we cannot be a party that serves the needs of billionaires and serves the needs of working class people, because those interests are against each other. These tech billionaire folks do not have the interests of working class people or everyday people in mind. They have their own interests, and they have a very specific belief about how we should advance the economy. It means advancing their profits. That was very clear,” Andrabi said. 

As Trump’s populist masquerade inevitably falls apart, resentments over inequality will return to the fore. Mass deportations aren’t going to solve anyone’s problems, and the infamous tariff plan will likely just fuel further economic resentment. The Democrats will have a decision to make: return to their roots as the party of the people and stand up to the politics of oligarchy, or try once more to operate within an imaginary middle ground between proto-fascism and democracy. 

They already have something to work with: Biden’s support of unions, his Build Back Better agenda (which was withdrawn in 2022 at the behest of moderate Democrat Joe Manchin), his antitrust initiative under Lina Khan, and his successful infrastructure investments. “That first half of the [Biden] presidency represented what a different Democratic party could look like,” Andrabi said. 

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But Biden pulled back, and his promised “bridge to a new generation” never manifested. “I think Kamala Harris had a real opportunity to say, you know, respect to President Biden, but these are a few of the things that I would do differently,” Andrabi added. She actively chose not to differentiate herself. 

“Instead, we left a lane for Republicans to be that alternative, which we know is not real.