Jeff Bezos Told Trump This Was His Worst Investment...and It's Hardly a Surprise

Matt Vespa | June 19, 2026 6:55 AM

There are no secrets in Washington, and there certainly aren’t any for billionaires whose lives are constantly under scrutiny. Their investments are also watched from afar, and for Amazon founder Jeff Bezos, there’s one he’d rather ditch yesterday. He reportedly told President Trump that buying The Washington Post was a huge mistake and that the people working there are downright terrible. Another thing Bezos mentioned was that the staff there don’t listen either. The publication was facing some financial struggles long before Bezos bought the paper (via NY Post):

Amazon founder Jeff Bezos called the Washington Post his worst investment in a conversation with President Trump months before gutting the newsroom, according to a new book by New York Times journalists Jonathan Swan and Maggie Haberman.
“The people there are terrible,” Bezos told Trump over dinner in December 2024, according to an excerpt obtained by The Post ahead of the June 23 release of “Regime Change: Inside the Imperial Presidency of Donald Trump.“
“They don’t listen. My other companies, they listen,” Bezos said, focusing his ire at the business side of the publication after losing more than $100 million that year.
About two months after the dinner, Bezos ordered the Washington Post’s opinion pages to promote “two pillars: personal liberties and free markets” — as subscribers peeled off in protest of the paper withholding its endorsement from Democratic presidential nominee Kamala Harris.
Bezos this February authorized the sweeping downsizing of the celebrated Watergate paper, eliminating roughly a third of its workforce, including all staff photographers and the sports section.