Jeff Bezos sat down with President Donald Trump at a private dinner in December 2024 and delivered a blunt verdict on The Washington Post: the paper was the worst bet he had ever made, and the people running its business side refused to follow his direction. The remarks, first reported by the Daily Caller citing a New York Post account of a forthcoming book, paint a picture of a media owner who had grown openly hostile toward the institution he purchased in 2013, and who found an unlikely confidant in the president his newsroom spent years trying to destroy.
"The people there are terrible," Bezos told Trump, according to the book. "They don't listen. My other companies, they listen."
Trump, for his part, had his own complaints. "This Washington Post is really unfair. You've got to take better care," the president told Bezos, per the same account. The two men arrived at the table with different grievances, one financial, one political, and apparently left with common ground.
The exchange comes from "Regime Change: Inside the Imperial Presidency of Donald Trump," a forthcoming book by New York Times reporters Jonathan Swan and Maggie Haberman. The New York Post published excerpts on June 17, 2026, and the details landed with force in a media industry already watching the Post bleed money and staff.
The Washington Post lost more than $100 million in 2024. That figure alone would rattle any owner. But Bezos's frustration, as reported, went beyond the balance sheet. He told Trump that the paper's business operations ignored the guidance he gave, a complaint that stands in sharp contrast to the obedience he expects, and apparently receives, at Amazon and his other ventures.
Trump recalled that Bezos said he had "lost half his friends" over the investment. Bezos disputed that framing, telling people that confidants had actually pushed him to sell the paper. Either way, the picture is the same: a billionaire who regrets buying a newspaper and a president who believes that newspaper treated him unfairly. They agreed on at least that much.
The December 2024 dinner was not an isolated gesture. The Washington Examiner reported that Bezos attended Trump's inauguration in January 2025 and had begun cultivating a relationship with the president the previous summer, even privately urging Trump to pick Doug Burgum as his running mate. Trump publicly praised Bezos afterward, calling him "a good guy" and noting, "I didn't really know him in the first term."
That shift, from adversary to dinner companion, was not lost on anyone in Washington. Bezos had already made waves in October 2024 when he published an op-ed in The Washington Post defending the paper's decision to skip a presidential endorsement for the first time since 1988. "Presidential endorsements do nothing to tip the scales of an election," Bezos wrote. The newsroom revolted. Subscribers canceled. But Bezos held firm.
The endorsement decision now looks like the opening act. What came next was far more consequential.
In February, Bezos cut roughly one-third of the Post's staff. Fox News reported that the cuts eliminated the paper's sports section, its books coverage, and several foreign bureaus, the kind of reductions that signal not a trim but a fundamental rethinking of what the paper exists to do.
Days after the layoffs, Publisher Will Lewis exited. The Post is now run by Jeff D'Onofrio, a former Tumblr and Google executive with no legacy-media pedigree, as acting chief.
Bezos also redirected the Post's opinion section toward personal liberties and free markets, a move that prompted the resignation of opinion editor David Shipley, as the New York Times reported in February 2025. The new editorial direction was explicit enough that former senior opinion editor Amanda Katz condemned it publicly. Newsmax reported Katz's assessment: "It no longer presents a variety of opinion but a propaganda push to benefit the owner."
That accusation says more about the accuser than the accused. For decades, the Post's opinion pages tilted reliably leftward. When Bezos steered them toward free markets, the old guard called it propaganda. The complaint is not that the pages became ideological, they always were. The complaint is that they stopped being ideological in the approved direction.
Bezos has been publicly crediting Trump with good ideas and calling the president more disciplined in his second term, a posture that would have been unthinkable during Trump's first four years.
Trump himself confirmed the evolving dynamic. He told reporters the two had dinner together the same night Bezos announced the opinion-page overhaul. "Unbelievable. I had dinner with Jeff Bezos last night," Trump said, per Newsmax's account.
Bezos is not the only tech titan who crossed the aisle. The Associated Press reported that at Trump's inauguration, top executives including Mark Zuckerberg, Sundar Pichai, Tim Cook, and TikTok's Shou Zi Chew were given prime seats traditionally reserved for family and honored guests. Elon Musk had already provided more than $200 million in assistance to Trump's campaign.
Trump was characteristically direct about the shift. "They did desert him. They were all with him, every one of them, and now they are all with me," the president said, referring to the tech leaders' previous alignment with Joe Biden. He added: "They're not going to get anything from me. I don't need money, but I do want the nation to do well, and they're smart people and they create a lot of jobs."
The migration of Silicon Valley money and influence toward Trump has drawn fierce criticism from the left, including Democratic candidates who have pledged to target Bezos over billionaire tax policy. But the backlash has not slowed the trend.
Bezos, for his part, has been willing to engage across political lines on policy questions as well. He recently backed a government efficiency push even after clashing publicly with a progressive mayor over tax proposals, a pattern that suggests his political positioning is driven more by pragmatism than ideology.
The most striking detail in the reported dinner exchange is not Bezos's frustration with the Post's finances. Losing $100 million is painful, but Bezos can absorb it. What stands out is the contempt for the institution's culture.
"They don't listen. My other companies, they listen." That is not the language of a patient owner waiting for a turnaround. It is the language of a man who has concluded that the organization's problems are its people, and that the people are not going to change on their own.
The staff cuts, the opinion-page overhaul, the publisher's departure, and the installation of a tech-industry outsider as acting chief all follow logically from that diagnosis. Bezos treated the Post the way he would treat an underperforming division at Amazon: he replaced leadership, cut headcount, and redirected the mission.
Trump's side of the conversation is revealing in a different way. The president recalled his own evolution on Bezos: "He said they write stories about him. And I didn't believe him the first time, first term. And I hated him for it. And then I believed him." That is Trump acknowledging that the Post's hostility was not just aimed at Republicans. It was aimed at its own owner, the man paying the bills.
Several details remain unclear. The specific venue of the December 2024 dinner has not been disclosed. It is not known who else, if anyone, attended. The publication date and publisher of the Swan-Haberman book have not been announced. And while the Daily Caller's account, citing the New York Post, attributes Bezos's "terrible" remark to the Post's business operations, the original quote does not draw that distinction on its face.
The Post's current financial position beyond the 2024 loss figure is also unknown. Whether the staff cuts and editorial changes have stabilized the paper's finances, or accelerated its decline, remains to be seen.
What is clear is that the man who owns The Washington Post sat across the table from the president his newsroom spent years opposing, and the two of them agreed: the paper's own people were the problem.
When the owner of a storied newspaper privately tells the president that his staff "are terrible" and "don't listen," that is not a management complaint. It is a verdict. And the layoffs, resignations, and editorial reversals that followed suggest Bezos meant every word.
