By Joshua Chaffin and Joe Flint

The world's third-richest man does not often show deference. But Jeff Bezos, the Amazon founder and space pioneer, is a businessman, like any other, trying to make his way in the era of Donald Trump.

Bezos joined the caravan of billionaires and tech titans who trekked to Mar-a-Lago to pay their respects in the days after Trump's election victory. His turn came on an evening in mid-December, when Bezos and his fiancée, Lauren Sanchez, dined with Trump and Melania. At some point in the evening, Elon Musk joined the party.

It was a strange tableau: Bezos wedged between the world's most powerful man and the world's richest man. Trump had smeared him and sought to brutalize his businesses during his first term in the White House; Musk is his business rival and sneering antagonist in the contest of billionaire space explorers.

For Bezos, that dinner was but one of a series of recent Trump-friendly gestures that have turned heads and prompted onlookers to wonder just what game he is playing as he positions himself for the second chapter of MAGA rule. Is Bezos putting on a patient and calculating defense, like a student of Sun Tzu's "Art of War," or has he undergone a Trump-era political transformation? Does he have fixed politics or principles, or is he governed more by shifting levels of testosterone and ruthlessness?

These questions apply not only to Bezos but to a coterie of fellow tech lords who appear to have blown with the Trumpian wind, most notably, Meta founder Mark Zuckerberg. He delighted Trump with his recent decision to end moderation on Facebook while jettisoning DEI policies at his company. Outwardly, the chain-wearing Zuck appears to have undergone a MAGA bro makeover.

Yet Bezos's seeming shift may be more surprising. During Trump's first term, he held the line as the new owner of the Washington Post, the newspaper of Watergate fame that cast itself for a new generation of readers as a leader of The Resistance. The paper paired its aggressive coverage of Trump with a tagline that expressed its sense of mission: Democracy Dies In Darkness.

That commitment came into question, however, in late October, 11 days before the election, when Bezos suspended the Post's longstanding practice of endorsing presidential candidates. The move deprived Democrat Kamala Harris of the paper's blessing and was intended, Bezos said, to protect the Post's credibility. The timing was awkward, to say the least.

Then came a million-dollar contribution by Amazon to Trump's inauguration, as well as the streaming service's $40 million deal with First Lady Melania Trump for an authorized documentary. The fee was three times the offer of the next-highest bidder, according to reporting by this paper.

There were the fawning tweets that Bezos lavished on a victorious Trump and his pride of place alongside other tech leaders at the inauguration -- Zuckerberg, Musk, Apple's Tim Cook and Google's Sundar Pichai, among others. Their seating on the dais just behind Trump, and in front of the cabinet, could be read in two ways: a historic assemblage of new-age wealth and power giving their support to the new administration, or a hostage video of billionaires held captive by a menacing strongman.

This week brought another bombshell when Bezos announced that the Washington Post's opinion pages would be devoted, henceforth, to defending the principles of "personal liberty and free markets." The rightward swerve prompted the resignation of the section's editor, David Shipley. Critics have denounced the move as an effort to stifle liberal dissent and criticism of Trump, while others have pointed out that such views are plentiful in other publications.

"I was stunned," Martin Baron, who was Bezos's first editor at the Post, said of his reaction. He called the changes "deeply disturbing...and a betrayal of the history of the Post."

In his 2023 book, "Collision of Power," Baron described Bezos as admirably shielding his staff from Trump's fury, even when his own businesses came under threat. "Do not worry about me. Just do the work. And I've got your back," he recalled his boss urging the staff in a July 2018 meeting.

Now, Baron views Bezos as just another billionaire trying to curry favor with the new administration. "You don't want to be on the wrong side of a vengeful president. And the president of the United States is the most powerful person in the world. And so as wealthy and powerful as Jeff Bezos is, well, Trump is more powerful still." he said. "So he's looking at that and saying: 'I've got to live with this.'"

In 2016, Trump was surrounded by buffers who blunted his most aggressive impulses. Now he commands a pack of pitbulls, distinguished by their willingness to do the boss's bidding. In one widely circulated photo from the inauguration, a smiling Bezos is shadowed by Trump's nominee for FBI director, Kash Patel, an election denier who has threatened to "come after the people in the media who lied about American citizens, who helped Joe Biden rig presidential elections."

"They're afraid. [Trump's] capable of doing anything," said a consultant who has advised other billionaires on their reputations and political dealings. "They're just being smart businessmen at the end of the day."

Bezos's defenders acknowledge that the timing and optics may be unfortunate for his changes at the Post. But the single-minded genius who revolutionized online commerce -- in fact, all commerce -- has never worried too much about timing and messaging. His calls are based on deliberation and deeply-held beliefs. He thinks in decades, not presidential administrations.

In this analysis, Bezos's biggest mistake was to allow the Post to drift too far left in response to a post-2016 climate of anti-Trump hysteria. As Bezos suggested in a memo to staff this week, his new mandate for the opinion section did not reflect MAGA priorities so much as his own principles.

"I am of America and for America, and proud to be so," he wrote. "Our country did not get here by being typical. And a big part of America's success has been freedom in the economic realm and everywhere else. Freedom is ethical -- it minimizes coercion -- and practical -- it drives creativity, invention and prosperity."

As for the attendance of so many billionaires at the inauguration, it was as much a jab at Biden, whom they came to detest for his antibusiness rhetoric, as an embrace of Trump.

In business terms, it is possible that moderating the tone of the Post's news coverage and sharpening the character of its editorial pages will attract new readers by helping to distinguish it from the rival New York Times. Bezos's defenders suggest that refreshing the Post to suit a changing era may please Trump without being expressly for Trump. That remains to be seen.

In the meantime, friends are aghast at how Bezos's own journalists have turned on him. "He came in as a conquering hero, and now that he is making his opinion known, everybody is up in arms," said Ari Emanuel, the Hollywood executive. "He owns the paper. He gets to make the decisions."

The Post was always an odd fit for Bezos. In his telling, he initially rebuffed Donald Graham, scion of the publishing family, who approached him to buy the paper. "I was not looking for a newspaper. I had no intention of buying a newspaper," Bezos recalled during a 2018 talk at the Washington Economic Club.

But Graham persuaded him of the merits of preserving a vital, if struggling, American institution and shepherding it into the digital era. Bezos paid $250 million for it in 2013, when the notion of a Trump White House still seemed hallucinatory.

He was hailed as a savior from Seattle for a hidebound East Coast institution, a guy with deep pockets who could lend technical acumen. And he promised to take a hands-off approach to what was written. "The values of the Post do not need changing," Bezos told readers in a note. "The paper's duty will remain to its readers and not to the private interests of its owner."

As for his politics, they were not easily discerned. Many, like Baron, describe them as "pragmatic" -- a mishmash of conservative economics and liberal and libertarian social values.

During the Obama administration, Bezos attended an intimate dinner that included the president, other entrepreneurs and Jon Stewart, according to the comedian. Stewart later recounted the night on his podcast, describing how the conversation turned to Bezos's view that the future economy would be centered on servicing the wealthy.

"So I said, like, 'I think that's a recipe for revolution,'" Stewart recalled. Then, he continued, "a hush falls over and then you hear Obama from across the couch go, 'I agree with Jon.'"

One former executive who worked for Bezos noted that "the only political vibe I got from Jeff was that he was basically a free-market person who did not like taxes." All the "lefty stuff," this person said, "came after 2017 and only accelerated as he was with Lauren Sanchez." Bezos gave $100 million to the Obama Foundation in 2021 in honor of the late civil rights leader and Democratic Congressman, John Lewis.

If Bezos's politics are a mystery, his personal transformation has been jarring and intensely public. He was once seen as the family guy, reveling in his cheapskate image -- using an old door for a desk and driving an ancient Honda. It was a homespun brand that belied Amazon's rapid decimation of mom-and-pop retailers.

But that changed. In a 2017 photo from the Allen & Co. summit in Sun Valley, Idaho, a buff Bezos -- jacked arms bulging, eyes hidden by sunglasses -- looks less like an aging billionaire than a billionaire's menacing bodyguard. Or perhaps a James Bond villain. (Amazon recently clinched a deal to take creative control of Ian Fleming's legendary spy series. "Who'd you pick as the next Bond?" Bezos wrote on X, announcing the news).

It was during Trump's first term that he left his bookish wife, MacKenzie Scott, and began dating Sanchez, a glamorous and adventurous former television journalist, in what has been either a Technicolor midlife crisis or a triumph of self-actualization. If they are not sailing one of the world's biggest yachts or skydiving, they are palling around with Hollywood friends like Orlando Bloom and Katy Perry. (Just this week Blue Origin, his rocket company, announced that it would blast Sanchez and Perry into space this spring.) Bezos and his fiancée are living their best billionaire lives in full public view.

The full-figured Sanchez stole the show at Trump's recent inauguration by wearing a daring bustier that caused even the statues in the Capitol to blush. The boldness of the fashion choice wasn't lost on observers. "I think the Masters of the Universe were always unapologetic," one media consultant said. "But now they don't have to hide it."

But if Bezos's personal life was thriving during Trump's first term, his business was becoming complicated -- chiefly because of the Post. Trump became obsessed with the paper and its relentless coverage of a special prosecutor's investigation into his Russia dealings, his business conflicts and payments he made to a former adult film actress.

The paper, and its owner, came to occupy an obsessive place in Trump's mind, and he spoke about it incessantly. He would publicly deride the paper as the "Amazon Washington Post" -- a lobbying tool that Bezos supposedly wielded to benefit his businesses and shield them from scrutiny. It was more than just talk: Trump tried to unilaterally raise the post office's shipping rates, a move that would have damaged Amazon's business, but he was informed he did not have the power to do so.

"He's always perceived Bezos as a political enemy for one reason and one reason only -- and that was the coverage of the Washington Post," said Baron.

In 2019, the cost of crossing Trump and funding the Resistance became staggeringly clear to Bezos. Amazon lost out to rival Microsoft on a mammoth $10 billion cloud-computing contract issued by the Pentagon. It was a surprising decision since Amazon Web Services was the industry leader in cloud computing and was judged by many to have presented a stronger bid.

In a lawsuit, Amazon accused Trump of political payback. The contract was canceled two years later, after he left office, and eventually parceled out among Amazon, Microsoft, Oracle and Google.

"Bezos did not cave under those circumstances. He stood his ground. He didn't put pressure on us," Baron recalled, praising his then-boss's "integrity and spine."

This time around, the risks to Bezos appear far greater. Trump 2.0 is faster, more ruthless and more skilled at pulling the levers of government power. Amazon is vulnerable on many fronts -- from antitrust to contracts. Then there is Blue Origin, Bezos's boyhood passion.

Like Musk, Bezos dreamed in childhood of going to the stars. It was the topic of his high school valedictory address. In a new era of space exploration, he and Musk are pairing private-sector drive and agility with multibillion-dollar government contracts. Musk's SpaceX has taken a commanding lead in the new space race. Under his new best buddy Trump, it is too easy to imagine even more of the government's largess and regulatory favor shifting his way just as Blue Origin is taking off.

Given all the headaches the Post poses for Bezos and his other ambitions, it is curious to many that he has not simply unloaded it. Why bother with the aggravation of fixing a newspaper if your dream is to go to the moon?

Journalist Kara Swisher, a leading chronicler of this tech era, has been trying to assemble a consortium of billionaires to save the Post from Bezos. "I'm talking to everybody. Like, everybody," she said on a recent episode of her Pivot podcast. "I don't know why he owns it. I know a Jeff Bezos that's different than this, let me say, who loves the challenge. And the Jeff Bezos behaving here is not the Jeff Bezos I liked."

Selling the paper now, at a time when it is bleeding money and subscribers, would be a blemish on Bezos's business record. As an aide noted, he has never been one to walk away from challenging problems. There is always the risk that the paper could go to a far worse steward.

And so, for the foreseeable future, it seems the Bezos and the Washington Post are stuck with one another, each threatening the other's legacy. As Bezos said in happier days, during that 2018 talk: "I know that when I'm 90 it's going to be one of the things that I'm most proud of -- is that I took on the Washington Post and helped them through a very rough transition."

(END) Dow Jones Newswires

February 28, 2025 21:00 ET (02:00 GMT)

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