In October 2019, Amazon sued the Pentagon, alleging that President Donald Trump had blocked the company from securing a $10 billion cloud-computing contract because of his animus toward The Washington Post and its owner Jeff Bezos—whom the US president derided as “Jeff Bozo.”
At the time, the dispute was just one example of the near-constant skirmishes between Trump’s White House and corporate America. But the episode left an enduring mark on Bezos, the Amazon founder and the world’s second-richest person.
Over the past year, Bezos has executed a sharp public reversal in his relationship with Trump—whom he previously criticised as a “threat to democracy”—that has surprised even longtime associates and has stunned the Post’s newsroom.
On inauguration day, Bezos stood dutifully beside other tech billionaires as Trump was sworn in. The ceremony, which was supported by a $1 million donation from Amazon, was streamed live on Prime Video. The platform has also paid $40 million for a Melania Trump documentary—nearly tripling the bid from rival studio Disney, though Amazon’s offer was for a limited series rather than a one-off program. Roughly $28 million of that sum will go directly in the first lady’s pocket, according to multiple people familiar with the matter.
Amazon recently paid to air old episodes of The Apprentice, Trump’s 2004-2017 reality TV show, on Prime Video—another way to send both money and flattery to the president. At The Washington Post, Bezos killed an editorial board endorsement of Kamala Harris and ordered the Post’s opinion section to only run articles about “personal liberties and free markets,” pledging never to publish views contrary to these principles.
Bezos’ empire includes a stake in the world’s largest ecommerce platform and cloud computing provider, and ownership of rocket maker Blue Origin and one of America’s most influential newspapers.
According to six people who have worked closely with him across Amazon, Blue Origin, and The Washington Post, the decisions are part of a marked shift in Bezos’ strategy toward Trump. These people painted a picture of a shrewd capitalist, making practical calculations to protect his businesses.
But they also believe Bezos is operating with a dose of fear about Trump, as well as resentment toward what he considers to be the Democrats’ “vilification” of Big Tech during the Biden administration.
Several of these people pointed to Amazon’s loss of that $10 billion contract for the Joint Enterprise Defense Infrastructure project (Jedi)—the knockout punch of Bezos’ ugly battle with Trump during his first term—as a watershed moment.
“There was a joke at the time that it didn’t cost Jeff Bezos $250 million to buy the Post, it cost him $10 billion,” the newspaper’s former editor Marty Baron tells the Financial Times.
A person who met Bezos days after the Pentagon blow says he was “deeply hurt” by the ordeal. “He sat there going: ‘This is not right.’”
For Bezos there are enormous financial risks to Trump 2.0. His business interests are vulnerable to the tax and tariff debates in Washington, and hold tens of billions of dollars in government contracts spanning national security and space. They are also subject to significant oversight and pressure from regulators.
Perhaps most important to Bezos is the future of Blue Origin, his passion project that aims to make space travel accessible, as the company vies to win US government contracts—often in competition with Elon Musk’s SpaceX.
Blue Origin is gaining momentum, successfully launching a heavy rocket into orbit in January and winning a contract to help send humans to the moon in 2029. But Bezos is still a distant second to Musk—whose company SpaceX has 450 orbital launches under its belt—and his rival’s proximity to Trump presents another danger considering the two billionaires’ frosty relationship.
A couple of weeks after November’s election, Musk posted on X that Bezos was “telling everyone that [Trump] would lose for sure, so they should sell all their Tesla and SpaceX stock,” forcing Bezos to reply “100% not true.”
One longtime adviser cautions: “He cares most about Blue Origin. His chance of being the player he wants to become in space could be destroyed” if the world’s richest man and most powerful politician united against him. “The growth trajectory for the entire enterprise depends on the federal contract... otherwise Blue is dead in the water.”
People close to Bezos dispute the idea that he is trying to get in the Trump’s administration’s good books to protect his business interests. “Jeff doesn’t make decisions out of fear or shape his actions to appease anyone,” says one. “The idea that any move he makes is some calculated attempt to gain favor is not only false, it misunderstands who he is entirely.”
A detached beginning
In the first two decades of Amazon’s life, Bezos distinguished himself by being largely detached from politics, even as the ecommerce company expanded to become one of the largest in the country—and transformed whole areas of the economy in the process.
“You want to know why Jeff has changed? It is part practicality driven by fear, mixed with a little opportunism,” says the adviser. “Jeff got frustrated with what he felt was demonization of tech by Democrats. It bugged him. Jeff felt like Biden went out of his way to get him and Amazon.”
Bezos has long been sympathetic to libertarian political views, according to people close to him, the result of having spent a lot of time as a child with his grandfather in Texas. “He likes tough Texas ranchers... he wants people to be independent and fix their own problems,” says a former Blue Origin executive.
But the close associate pushes back on the notion that Bezos has genuinely shifted politically toward Trump. “I don’t think he is showing his true colors, [this is] not the Jeff I know. I just don’t believe he suddenly thinks Trump is the answer.”
“He may not be all in [on Trump], but he’s not stupid,” says another former senior executive at Blue Origin. “It’s a matter of preservation.”
Baron views the heel-turn as largely a business matter. “Am I to believe that the company that is the source of his wealth, and [the one that] is the focus of his passion, are totally irrelevant to him in all of this? Honestly I’m just not that naive,” says Baron, who steered the Post through the first Trump administration and the Bezos acquisition as editor from 2012 to 2021.
Now age 61, Bezos has changed physically too, Baron and others note, having bulked up to the physique of a bodybuilder. His personal life also transformed when he became tabloid fodder in 2019, divorcing his wife of 25 years after an affair was exposed in the National Enquirer. He is due to remarry this summer to former television anchor Lauren Sanchez.
Bezos’ stark turn toward Trump might be in the best interests of the companies he founded. But it has alarmed the editorial staff at The Washington Post, fueling an exodus of talent and reportedly hundreds of thousands of subscribers from the newspaper that famously broke the Watergate scandal in the 1970s.
David Maraniss, a Pulitzer Prize-winning editor who has worked at the Post for 50 years, recently pledged to “never” write for the newspaper while Bezos is owner. Maraniss tells the FT that the mood at the paper is “dire, anxious, uncertain, angry, bereft.”
“I’m almost at the point where I just wish they could change the name of the paper, because it’s not The Washington Post any more.”
Trump, meanwhile, approves. “I’ve gotten to know him, and I think he’s trying to do a real job... with The Washington Post, and that wasn’t happening before,” Trump said in a television interview on Sunday.
Growth and engagement
As Bezos’ business empire has grown, so have its links with the government.
Amazon and Blue Origin hold more than $20 billion in outstanding federal contracts, including the lunar mission and a $10 billion contract between the National Security Agency and its cloud arm, Amazon Web Services.
In the aftermath of the 2019 Jedi decision, Amazon filed its lawsuit alleging that the contract award to Microsoft had taken place due to “improper pressure” from Trump. The Post’s coverage had placed Bezos in Trump’s “crosshairs,” the lawsuit alleged, and cited an article that claimed the president had discussed ways to “fuck with him [Bezos].”
“The lawsuit was hyperbolic, but it was grounded in Jeff’s thoughts,” says a person familiar with the matter.
Although the government reopened bidding, it later axed the project under Biden. A subsequent multibillion-dollar cloud contract was split between Amazon, Microsoft, Google, and Oracle.
“In the first administration Jeff was battling with Trump because Trump was coming after him, not because he was some super-progressive,” says a person familiar with Bezos’ decision making. “At the time he believed in the mission of the Post and said the damage to Amazon was worth the cost.
“But now Trump is back, that attitude is a casualty of the danger presented,” the person adds.
Bezos and his Big Tech peers are also seeking a de-escalation of the Biden-era regulatory crackdown led by their bête noire Lina Khan, former chair of the Federal Trade Commission. In 2017, when studying at Yale Law School, Khan wrote an article titled “Amazon’s Antitrust Paradox” criticizing “predatory pricing” and calling for the ecommerce giant to be broken up.
Six years later, as head of the FTC, she sued the company for running a monopoly that seeks to “inflate prices, degrade quality, and stifle innovation.” The landmark case is scheduled for trial in October 2026.
“What Bezos and other tech titans have at stake is the FTC, and whether the [new] government is going after them for being monopolies,” says Todd Harrison, a senior fellow at the American Enterprise Institute think-tank. “The deference to Trump is about preventing direct legal action.”
Bezos fears that the government might seek to make an example of Amazon rather than its tech rivals such as Google and Microsoft, according to two people familiar with the matter. However, Khan’s replacement as FTC chair, Andrew Ferguson, has so far shown no sign of easing scrutiny of Big Tech.
“With Trump it’s less about what he can take away so much as where he might apply the pressure,” says one former Blue Origin executive.
Another close associate says that any move by Trump to deprioritize lunar missions in favor of Musk’s aspirations to reach Mars would have a significant impact on the company’s viability and success.
“It is what he has always dreamt of,” the associate says. “Nothing will hurt Jeff financially—Blue is a money loser. It is more the opportunity to be involved.”
Even during the periods when he has been sparring with Trump, Bezos was careful to meet the president whenever requested and found redeeming qualities. He would praise Trump’s “savvy” and tell aides that “he is smarter than you think,” dismissing much of his behavior as “bombastic theatre,” one associate remembers.
In a December interview after Trump’s victory Bezos described him as a changed man: “calmer than he was the first time—more confident, more settled.”
Bezos has also been careful to cultivate social and financial ties with his family.
In January 2020, he hosted an inauguration after-party of the exclusive Alfalfa Club at his mansion in DC’s Kalorama neighbourhood, inviting non-members Jared Kushner and Ivanka Trump as well as Trump adviser Kellyanne Conway. Ivanka Trump and Kushner also attended Bezos’ holiday party at a sushi restaurant in Aspen late last year.
A person close to Bezos admits that the deal for the Melania Trump documentary “is patently ridiculous, but is very pragmatic.” The person adds: “He is doing a deal, offering money to buy the Trump family’s affection and flattering the president. If you think about it in terms of costs versus benefit, it is pretty low. It’s a smart investment.”
Amazon says it signed the deal for the Melania Trump documentary “for one reason and one reason only—because we think customers are going to love it.”
