Amazon founder Jeff Bezos branded The Washington Post the worst bet of his career during a private meal with President Donald Trump weeks before he carved up the newsroom.

The billionaire vented on the paper at a December 2024 dinner, according to the New York Post, citing the forthcoming book “Regime Change: Inside the Imperial Presidency of Donald Trump,” authored by New York Times reporters Jonathan Swan and Maggie Haberman. “The people there are terrible,” Bezos told Trump, per the Post. He griped that the publication’s leadership ignored his guidance. “They don’t listen. My other companies, they listen,” he said.

Notably, The Washington Post has suffered significant financial difficulties in recent years — a point of contention for Bezos, especially with the business side of his newspaper property. In 2024, The Washington Post lost more than $100 million.

Trump used the same dinner to air his own complaints, the New York Post reported. “This Washington Post is really unfair. You’ve got to take better care,” he told Bezos. The two men landed on common ground despite different grievances. (RELATED: ‘Difficult Decisions Have Been Taken’: Washington Post’s CEO And Publisher Resign After Wide-Ranging Staff Reduction)

A murkier motive surfaced in Swan and Haberman’s casting of the conversation. “In Trump’s telling, Bezos told him he had lost half his friends over the investment,” the authors wrote, according to the New York Post. Bezos disputed that account to others, saying confidants had pushed him to sell rather than that friendships had collapsed.

Jeff Bezos told Trump the Washington Post was his worst investment before slashing staff: ‘People there are terrible’ https://t.co/IuoYGIth6g pic.twitter.com/jDfCTWmHSc

— New York Post (@nypost) June 17, 2026

Trump admitted he once loathed the Amazon chief over the paper’s coverage. “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 recalled in the New York Post. “And then I believed him.”

The dinner followed the Post’s decision to skip a 2024 endorsement, which Bezos defended in an October op-ed. “Presidential endorsements do nothing to tip the scales of an election,” he wrote. Opinion editor David Shipley resigned after Bezos redirected the section toward personal liberties and free markets, the New York Times reported.

Bezos gutted roughly a third of the staff in February, NPR reported. Publisher Will Lewis exited days later. Acting chief Jeff D’Onofrio, a former Tumblr and Google executive, now runs the paper, according to Axios.