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Crossed Wires: Which billionaires have not bent the knee to Trump?

As tech titans trade their blue capes for red ones in the shadow of Trump’s tumultuous reign, a few brave souls cling to their liberal values, indicating that some billionaires still dare to dream of a progressive future—albeit with a healthy dose of caution.
Crossed Wires: Which billionaires have not bent the knee to Trump? SA’s G20 themes of equality, inclusiveness and sustainability seem diametrically opposed to the philosophy of US President Donald Trump, seen here at a Nato summit in The Hague last month. (Photo: Remko de Waal / EPA)

Bezos of Amazon, Musk of X/Tesla, Zuckerberg of Meta and Andreessen of Andreessen Horowitz have all shed blue cloaks since Trump’s ascendance and donned bright red ones. Some others have shifted more quietly and pragmatically, perhaps making some allowance for the new winds of politics and a vengeful president.

These are not normal times, of course. The current president is slashing and burning any entity that does not toe his thick red line, whether they are Harvard, CBS, NPR, Voice of America or Associated Press. Not to mention Canada, for God’s sake. It is unprecedented. A large pair of balls is required if you want to refuse to pay obeisance – there are real consequences, as we have seen.

It is with this in mind, and catalysed by the stunning success of self-declared socialist Zohran Mamdani in the New York Democratic mayoral candidate race last week, that I set out to find some tech bros who remain committed to good old liberal values and who continue to talk about climate change and renewables, as well as DEI and trans and immigrants’ rights, as though Maga had never happened.

It turns out that there are still quite a few – some more vocal and others keeping quiet. Perhaps these “woke” holdouts will feel the wind at their backs again in 2028. Politics is fickle and forgetful, and public perception apt to balance on the wobbly fence of economic good times.

No-man’s-land

Let’s dispense with those who have been careful to stay in no-man’s-land. Tim Cook of Apple has stayed partially out of the fray. He made the trek to Mar-a-Lago to dine with Trump early on, if only to say, “We are as happy to work with you as with all other presidents.” Then he got into a small spat with Trump about where to manufacture iPhones, which argument seems to have dissipated, probably because Trump was informed that iPhones simply cannot be manufactured in the US at a competitive cost.

How about Sergey Brin and Larry Page of Alphabet/Google? They are both longtime left-leaning centrists who have managed to stay out of the debate by saying little and keeping their personal opinions private.

Jensen Huang of Nvidia, on the other hand, has found himself in a bit of a pickle. In 2016, he was quoted as saying, “In general I prefer a more liberal government”, but now, at the head of what is possibly the US’s most politically sensitive technology, AI, he has to make nice with the administration that holds all the keys to sanctions and IP restrictions. Mind you, what with Nvidia’s dominance in AI hardware, the Trump administration has to make nice with Huang too, so Trump and Huang exist in a politely necessary co-dependent relationship. They are not bros.

Anti-Trump brigade

This brings us to the others – the ones who clearly do not like Trump and will not bend the knee, the ones whose moral compass has not changed. (I am not passing judgment here on whether that moral compass’s needle is pointed in the right direction, only that it seems not to have moved.)

These include, most notably, Mark Cuban. Cuban made his fortune in streaming in the late ’90s and has since diversified promiscuously. He is (like many self-made-billionaires-at-40) brash, opinionated and smart. He has accused Trump of being a “snake oil salesman”, of being scared of “strong, intelligent women”, of being “a threat” to the US and of having “fascist tendencies”. He has been critical of the Democrats, too, accusing them of “not being able to sell shit” but he has also remained steadfastly outspoken on core left-wing planks like DEI.

Then there is Reid Hoffman, co-founder of LinkedIn. His outspoken criticism of Trump caused him to consider leaving the US when Trump was re-elected (out of fear of retribution), but he has not done so and continues to actively support Democratic causes and candidates. And Reed Hastings, co-founder of Netflix, remains firmly “progressive” except for his controversial support of private over public schooling, which has put him at odds with traditional Democrats.

Finally, Satya Nadella of Microsoft. He is also seemingly untainted one way or the other, is unfailingly diplomatic and not given to political statements. But Microsoft’s contributions tell a different story – they are 4:1 in favour of the Democratic Party.

Billionaire influence

The narrative in its entirety tells an interesting story. These people have enormous influence and deep pockets. Where they lean has direct influence on the direction of US governance, not only via their monetary contributions, but in terms of the messages they implicitly whisper to their large customer bases.

So, why have some moved to the right, either publicly or privately? Mark Andreessen, in a recent podcast, described a meeting at the Biden White House with other tech executives and some of Biden’s team. The subject was AI regulation. At the conclusion of the meeting, the executives went downstairs and huddled in the parking lot. One of them said, “So I guess it’s Trump for us?” They all agreed, at least in Andreessen’s telling. For them, the issue was government regulation, nothing else.

It was not the money, or at least not completely. It was what Andreessen and the others saw as clumsy and constraining government interference in the sort of innovation they believed to be a national imperative.

It may be the case that some of these billionaires left their longtime political homes because Democratic policies pushed them away, but I suspect others moved to the right (and particularly toward Trump) because that’s where the money is. Perhaps also because no one wants to deal with Trump’s wrath. 

The only way we’ll know for sure is if and when a new Democratic president is elected and the Zuckerbergs and Bezoses come crawling back or not. Only then will we know whether they are motivated by money or principle. DM

Steven Boykey Sidley is a professor of practice at JBS, University of Johannesburg a partner at Bridge Capital and a columnist-at-large at Daily Maverick. His new book, It’s Mine: How the Crypto Industry is Redefining Ownership, is published by Maverick451 in SA and Legend Times Group in the UK/EU, available now.

Comments (3)

Lawrence Sisitka Jun 30, 2025, 08:56 AM

Everyone with any cojones worthy of the name needs to simply stand up for the best human values, and against the trash that Trump is hurling in every direction. How much more do people already obscenely rich need in order to behave like real caring people? We all need to stand up against the filth that passes for US governance these days. Even to the extent of letting the US sink in the trumpit of its own making. But power to Harvard and the others who won't be cowed by the cowardly bully.

MT Wessels Jun 30, 2025, 12:51 PM

Well put. Imagine being a billionaire - forking out $50m for a tawdry, botox-fueled wedding - but deciding you still need more money. Zuck, Besos, Thiel, Musk, the lot. These guys never really cared, it was simply hubris. So when Trump-the-useful-idiot promised to help them pay less tax and shirk greater-good oversight over their rapacious business models, they droppped the pretense, lickety-split. The world's citizens have more pressing needs than FBook, Tesla and Amazon.

William Stucke Jul 3, 2025, 07:12 PM

Perhaps you aren't aware that the primary reason that Trump and Musk are no longer "pals" is Musk's objections to Trump's "big, beautiful bill" that will reduce taxes on the rich, reduce services to the poor, and increased the USA's debt. The man may be lacking in social skills, but his core philosophy is pro-humananity. Trump, on the other hand, is simply pro-Trump.

kanu sukha Jun 30, 2025, 01:02 PM

At our peril, we forget that T.... is a multiple times convicted felon ( according to US legal standards - sic ) but has not yet served a single day in jail! Imagine the president of South Korea getting away with *hit like that ? Now he is going as far as 'pardoning' the ICC wanted criminal in the 51st state of the US - Israel ! Next it will be the recent cold blooded murderer of the two Dem reps (the enemy within) in parliament . The Dems with their Republican (light) policies ... exposed by Mamdani ... do not deserve to 'rule'. Their 'sidelining' of Bernie from running against Trump in his first term, is a stain they will never recover from unless a 'bunker buster' is dropped on them.

megapode Jun 30, 2025, 03:05 PM

Too many businesspersons are primarily concerned with the bottom line and an absence of regulation so that they can do what they like to grow that bottom line. Musk is not pulling out of California because he doesn't like wokeness. He is pulling out because they are limiting the number of rocket launches with the attendant safety measures, clean ups and road closures. He will go somewhere we has more freedom to launch as he likes.

Michael Cinna Jun 30, 2025, 04:49 PM

This article and author is an excellent example of the moral confusion of left-wing progressive politics and their perputual purity tests – as well as the theft of classical liberalism (“good ole liberal) and Libertarian philosophies that they have claimed for their own. DEI stands at the polar opposite of liberal political philosophy. Identitarian (intersectional) politics and looking for billionaires to back your flavor of politics is not liberalism. It’s just tribalism.

William Stucke Jul 1, 2025, 09:40 AM

An insightful comment, Michael. Thank you. There is this strange concept, popular in the media and in academia that Left is "nice" and Right is "nasty". And that Neoliberalism is "extra nasty". Being a Liberal is primarily about recognising the right of others to do as they wish, provided that they cause no harm to others. How can this be considered "nasty"? Moving away from the Centre in either direction progressively becomes about telling others what to do, woke or PC or . . .

Michael Cinna Jul 3, 2025, 02:50 PM

First, the Left/Right spectrum is kept alive by race and identitarian grifters. Its a useless and outdated tool for analysing political systems/philosophies. CLiberalism is fudnementally underpinned by the non-coercion principle and its consent culture in praxis. Not surprised about Academia - there's been multiple studies about the mono political culture of academia and the lack of diversification in political thought and culture. Universities are pumping out activists