Jeff Bezos told Donald Trump over dinner in December 2024 that the Washington Post was his worst investment and that the people there were terrible, a blunt private judgment that came before he approved a sweeping February downsizing at the paper. The cuts eliminated roughly a third of the workforce, along with all staff photographers and the sports section.
The exchange matters now because it recasts later newsroom cuts as the end point of a view Bezos had already made clear in private. In the dinner conversation, he said the paper did not listen and added that his other companies did. Trump, for his part, said the Post was really unfair and told Bezos he had to take better care.
Bezos had lost more than $100 million that year, and about two months after the dinner he ordered the paper’s opinion pages to promote two pillars: personal liberties and free markets. The shift landed after subscribers peeled off in protest when the Washington Post withheld its endorsement from Kamala Harris, turning a long-simmering ownership fight into a business problem that could be counted in cancellations.
Trump later said in an interview for the book that he hated Bezos during his first term because he believed, wrongly, that Bezos controlled what the newspaper wrote. He said he heard that the paper wrote stories about him, did not believe it at first, and only later accepted that Bezos was not the one making every editorial call. That gap between Trump’s suspicion and Bezos’s insistence that his frustration was with the business side, not the newsroom itself, is the sharpest friction in the account.
The excerpt comes from Regime Change: Inside the Imperial Presidency of Donald Trump, by Jonathan Swan and Maggie Haberman of. It places Bezos’s candor inside a broader push by Big Tech figures to smooth relations with the incoming president, while the Washington Post was already in turmoil from the endorsement fight and the cuts that followed. Will Lewis, the paper’s former publisher and CEO, was removed after the mass firings, and Jeff D’Onofrio stepped in and said he was going to fight like hell for this institution.
D’Onofrio has also approved new content and licensing deals aimed at bringing in revenue from OpenAI, Apple News+ and Alexa+, a sign that the paper’s next phase is being built around new money as much as old newsroom craft. What is still unresolved is how far that repair job can go after a February cut that took out a third of the staff and left the Post trying to rebuild while its owner keeps pushing it toward a different business model.
