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The messegner video chat sexsight of Elon Musk, Jeff Bezos and Mark Zuckerberg sitting together at Donald Trump's inauguration — as they reportedly will do Monday — would be a shock for their 2016 selves.

Back then, these titans of the tech world were way to the left of Trump, whose political stances put him about as far to the right as Republicans get, then and now.

Musk, once a vocal Barack Obama supporter, voted for Trump's opponent Hillary Clinton in 2016. The Bezos of that year blasted candidate Trump for "eroding democracy." Zuckerberg didn't make an endorsement, but the issues he put his money behind at the time — social justice, inequality, easing the immigration process — put him squarely on the Democratic side of the political line.

The most vocal tech world supporter of Trump in 2016, Paypal co-founder Peter Thiel, was seen as an outlier back then: Silicon Valley was solid blue. Now the outlier is Nvidia CEO Jensen Huang, who hasn't donated to Trump's inauguration fund and won't be attending.

All the other big names in tech will be there: Apple's Tim Cook, Google's Sundar Pichai, Microsoft's Satya Nadella, OpenAI's Sam Altman, and TikTok's Shou Chew, have all donated $1 million or more, and all save Altman will be in attendance.

What happened? It wasn't just that these men were made so much richer by a stock market rally following Trump's election in November. A similar rally happened in November 2016 as well, and it didn't make tech CEOs any less reluctant at a Trump Tower meeting with the president-elect. That was the roundtable where Thiel's smile stood out in a sea of grimaces.

The process of tech leaders learning to love Trump may have begun piecemeal during his first administration. But it only really kicked into high gear over the course of 2024, with a speed and ferocity that has left many observers' heads spinning. No wonder President Biden, in his farewell address, warned of a tech-led "oligarchy" that may threaten democracy itself.

To understand what happened, let's take a look at the three richest tech bros, who also happen to be the three wealthiest men in the world, and the journey they took from opposing Trump in 2023 to sitting together at his inauguration in 2025.

Elon Musk

Nowadays, of course, Musk is so central in Trump's camp that he is sometimes described as the incoming "co-president." He donated $250 million, spoke at Trump rallies, called himself "Dark MAGA," and clearly put more than a thumb on the scale for Trump on Twitter/X throughout the fall of 2024.

Musk's America PAC seized the @America account from its original owner, and even now faces a fresh lawsuit from Pennsylvania's Attorney General over that PAC's dubious $1 million lottery for swing state voters.

But it's important to remember that Musk wasn't always this far right, and his turn towards Trump came fairly recently. Yes, he joined Trump's business council in 2017, but he also quit when Trump withdrew the U.S. from the Paris Climate accords. Back then, the Bay Area-based Burning Man attendee was still happy to support Pride month.

Musk drifted rightwards during the pandemic years, when he moved Tesla HQ to Texas and, according to reports, began feuding with his trans daughter. The drift seems to have accelerated when he bought Twitter in 2022, started tweeting about the "woke mind virus," and endorsed the GOP (unsuccessfully) in that year's midterm elections.

Even then, Musk was no Trump fan. In 2023 he helped launch Florida governor Ron DeSantis' presidential campaign in a disastrous Twitter Spaces. Musk's statement that Trump should "sail into the sunset" prompted a brief feud with the former president. "I could have said, "drop to your knees and beg," and he would have done it," Trump responded, recalling an Oval Office meeting in his first term.

Then came 2024, and three key events. First, DeSantis dropped out in January. Then on May 31, Donald Trump's conviction in a New York courtroom over hush money payments that possibly swung a close 2016 election his way. Musk fumed that the charges were "trivial" and politically motivated. By then, perhaps not coincidentally, Trump was already talking to Musk about a possible advisory role — and we were starting to learn just how many federal agencies were investigating Musk.

But the deal was sealed in July when Trump survived a shooting in Butler, Pennsylvania. Musk "fully endorsed" Trump on Twitter that day, then made his first appearance with Trump on his return to Butler in October.

By then, Trump had already promised Musk his Department of Government Efficiency, or DOGE, the advisory group that Musk is set to lead along with fellow billionaire Vivek Ramaswamy. The latest reports on DOGE say that Musk will have an office inside the White House itself.

Notably, Musk did not have to drop to his knees and beg for any of this. Which leads us to wonder: who is really on whose leash here?

Jeff Bezos

In the 2016 election, Amazon founder Jeff Bezos was one of Trump's most outspoken critics in the tech world. A month after Trump entered the White House, Bezos' Washington Postunveiled its pointed new slogan, echoing its owner's warnings: "Democracy dies in darkness." Bezos and the Post's coverage continued to earn Trump's ire.

Two years later, in an equally pithy Medium post, Bezos attacked Trump ally David Pecker, head of the company that owns the National Enquirer, for what Bezos said was blackmail over nude photos of the billionaire.

But a curious thing had started to happen by then. With his growing wealth, which spiked in the late 2010s, plus his new marriage and new yacht, Bezos started to develop a serious case of Rich Guy Brain. By 2022, his tone on social media had changed entirely, becoming much more Musk-like. No longer was Bezos skewering his Trumpian opponents for literally threatening to expose his ass; instead, he was discussing compliments on his ass.

Finally came the moment that Bezos' opposition broke. His top lieutenant at thePosttold staffers there would be no presidential endorsement in 2024 — which, if democracy was still at risk, seemed a curious case of fence-sitting. (Indeed, the Post staff had prepared a Kamala Harris endorsement that was effectively spiked.)

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More than 200,000 Postsubscribers cancelled their subscription in disgust. Still, Bezos seemed unmoved. This time he penned a piece explaining that newspaper endorsements didn't matter. It was, he said, a complete coincidence that Trump was visiting his space company Blue Origin the same day.

After the election, Bezos continued his shift towards Trump. In a December interview he said the incoming president was "calmer" and had "grown a lot over the last eight years." Time will tell whether that's true, or whether Bezos has simply shifted to the side of Dark MAGA.

Mark Zuckerberg

Unlike Musk and Bezos, who moved Trumpwards all at once, the Facebook founder seems to have slalomed back and forth in his attempts to placate Republicans in Washington since Trump first took office.

Prior to Trump's first election, Zuckerberg was easily the most liberal of this Big Tech trio. As a New York Timesinvestigation during election season noted, he helped found Fwd.us, an advocacy group dedicated to giving undocumented immigrants a path to citizenship. The Zuckerberg-Chan initiative spent nearly half a trillion dollars on causes such as legalizing drugs, reducing the number of people in U.S. prisons, and promoting universal healthcare.

But then in the immediate aftermath of the 2016 election, Zuckerberg quickly tossed aside claims that unchecked fake news on Facebook had contributed to Trump's victory. He later regretted that stance, but not enough to avoid being dubbed Misinformer of the Year in 2017 by the watchdog group Media Matters for America.

Zuckerberg's response to Trump's first election was twofold: he minimized the presence of news posts in Facebook feeds, which unintentionally contributed to a widespread crash in readership for media entities. And he set up a fact-checking service, which often earned the ire of conservative groups. The fact-checking service was nuked in January 2025, pleasing the incoming Trump administration.

Often wanting to appear amenable to conservative concerns about the news feed and which stories get promoted, Zuckerberg made repeated changes to the algorithm that boosted pro-GOP voices. When internal data showed right-wing news sites like the Daily Caller were getting more interactions on Facebook than anyone else, Zuckerberg nixed the release of that data.

The more amenable he is, however, the more conservative voices (including Musk) complain — an old tactic called "playing the ref." Now Zuckerberg has morphed again, apologizing even for his donation to election integrity groups in 2020. Most recently, he told Joe Rogan that corporate America needs more "masculine energy."

What that means for the social media giant remains to be seen, but America is certainly about to get a lot more oligarch energy from Zuck and his fellow tech bros.