The Washington Post has been a mess for years, and even its own owner knows it.
Now the man who owns it went to Mar-a-Lago and said so to the one person on earth who hates the paper most.
And what Trump did next behind Bezos’ back is something the Amazon billionaire probably wishes he never found out about.
The Dinner Nobody at the Post Wanted to Hear About
In December 2024, just weeks after President Donald Trump won his second term, Jeff Bezos traveled to Mar-a-Lago for a private dinner with the incoming president. According to the forthcoming book Regime Change: Inside the Imperial Presidency of Donald Trump, written by New York Times reporters Maggie Haberman and Jonathan Swan, Bezos spent part of that dinner unloading on the newspaper he has owned since 2013.
Bezos complained to Trump that The Washington Post was “the worst investment I’ve ever made.”
The authors quoted Bezos as saying of the business side of the Post, “The people there are terrible. They don’t listen. My other companies, they listen.”
Trump, who spent years calling the paper “failing” and an enemy of the people, was not exactly a sympathetic ear chosen at random. Trump told Bezos, “This Washington Post is really unfair. You’ve got to take better care.” The two men were, by all accounts, commiserating over a paper that neither of them seemed to think much of.
Haberman called it “wild” to find out about the two complaining together over dinner, saying both men probably had “different reasons” for hating on the paper, but that they were united in their disdain.
Trump Came Around on One Thing
For years, Trump assumed Bezos was personally directing the Post’s coverage against him. That changed. At first, Trump hadn’t believed Bezos when the billionaire told him that he couldn’t control the Post’s coverage. As proof, Bezos told Trump that the newspaper’s reporters would write negative stories about him, too.
Trump eventually accepted that explanation. “He said they write stories about him. And I didn’t believe him the first time, first term. And I hated him for it,” Trump said. “And then I believed him.”
The book said Trump claimed Bezos told him that buying the Post had cost him friendships, though the authors wrote that Bezos later said people close to him had urged him to sell the newspaper.
The Groveling That Amused Elon Musk
Here is where the story gets a little richer. While Bezos was apparently trying to build goodwill with Trump by trashing his own newspaper, Trump was telling other people about it and laughing.
“You would not believe the texts I got from these tech guys,” Trump told associates, according to the book. “I’ve got to show you.” “Think of where these guys were in 2016,” Trump reportedly told Elon Musk. “They hated me. They were doing everything they could to knock me down. And look at them now.” “First-class groveling,” Musk replied.
Haberman and Swan told the show that despite the dinner where they both bashed the Washington Post, there were other times Trump mocked Bezos and Meta CEO Mark Zuckerberg for “sucking up” to him. Swan said Tesla boss Elon Musk especially got a kick out of the “first class groveling” from his tech rivals.
Bezos was not alone in this. The drive by tech billionaires to ingratiate themselves with Donald Trump as he returned to the White House was hardly subtle. At the inauguration, figures including Amazon’s Jeff Bezos, Apple’s Tim Cook, Meta’s Mark Zuckerberg and Google’s Sundar Pichai were there, standing behind Trump as he was sworn in in the Capitol Rotunda. Haberman and Swan write that Trump relished the spectacle of the tech titans “kissing my ass.”
What Bezos Was Actually After
The book makes clear this was not just a social call. In July of last year, Bezos met with the president in the Oval Office where he pitched opening up lucrative federal contracts to his space exploration firm Blue Origin in hopes of competing with Musk’s SpaceX. Trump told Bezos he would take the idea under consideration, but it ultimately went nowhere.
So Bezos dumped on his own reporters, tried to get a piece of federal space contracts, and came away with nothing except a president who was mocking him to Elon Musk. While Bezos may have believed he was currying favor with Trump, he ended up trashing his own newspaper to a president who was ridiculing him behind his back, earning little respect in return for the effort.
The Post, for its part, has been in a rough stretch by any measure. The Post laid off one-third of its staff in February 2026, eliminating its sports section, books coverage and several foreign bureaus. “We can’t be everything to everyone,” executive editor Matt Murray told staff in a note. Will Lewis, the paper’s former publisher and CEO, stepped down days after the layoffs.
The Washington Post faced subscriber backlash after withholding its 2024 presidential endorsement, followed by changes to its opinion section and sweeping staff cuts under Bezos’ ownership.
Bezos did revamp the opinion section, reorienting it around what he described as two guiding principles. “We are going to be writing every day in support and defense of two pillars: personal liberties and free markets,” Bezos wrote in a note to staff. Whether that shift came from genuine conviction or from a calculation about how to stay on the right side of the incoming administration is a question the book leaves readers to answer for themselves.
What the Book Actually Is
Maggie Haberman and Jonathan Swan’s Regime Change: Inside the Imperial Presidency of Donald Trump is based on more than 1,000 interviews conducted over three years. The 496-page book, published by Simon & Schuster, covers a presidency the authors describe as unconstrained by the limits that defined Trump’s first term, with coverage spanning military operations, Justice Department decisions, and his administration’s approach to foreign policy.
The Bezos-Trump dinner is one piece of a much larger picture the book assembles. But it is one of the more revealing pieces, because it captures something that tends to get lost in all the coverage of Trump’s complicated relationships with the media: the people who run these institutions often hold their own employees in pretty low regard, and sometimes they say so to others.
Bezos bought the Post in 2013 for $250 million. He has watched it lose subscribers, burn through leadership, and bleed credibility on multiple fronts. Going to Mar-a-Lago to tell the president it was his worst investment may have felt like diplomacy. It read, at least to the people in that room, like something else entirely.
Operating as an anti-Trump political operation alienated regular Americans.
Haberman and Swan’s book promotion comes as they are making the media rounds to discuss their reporting. The Washington Post declined to comment on the book’s contents.
Sources: Mediaite; Status News; Fox News Digital; Deadline; Variety; Poynter