Jeff Bezos Called the Washington Post His Worst Investment Before Authorizing Major Staff Cuts

Amazon founder Jeff Bezos characterized the Washington Post as his worst investment during a December 2024 dinner conversation with President-elect Donald Trump, according to excerpts from a forthcoming book by New York Times journalists Jonathan Swan and Maggie Haberman. The candid remarks preceded Bezos's authorization of substantial workforce reductions at the newspaper months later. The revelation underscores tensions between major technology figures and traditional media outlets as political leadership transitions.

During the December dinner, Bezos expressed frustration with the publication's business operations, stating that personnel there were unresponsive to his direction. "The people there are terrible. They don't listen. My other companies, they listen," Bezos told Trump, according to the book excerpt titled "Regime Change: Inside the Imperial Presidency of Donald Trump," scheduled for release in June. His criticism focused specifically on the business side of the organization, which had generated losses exceeding $100 million that year.

Trump, who had previously criticized the Post's coverage during his first administration, found common ground with Bezos during the encounter. Trump told Bezos: "This Washington Post is really unfair. You've got to take better care." However, the two men harbored different grievances about the publication. Trump blamed the newspaper for unfavorable reporting, while Bezos's concerns centered on management responsiveness and financial performance rather than editorial direction.

In February, approximately two months after the dinner conversation, Bezos authorized a major restructuring of the newsroom that eliminated roughly one-third of the workforce. The cuts included the elimination of all staff photographers and the sports section, representing one of the most significant reductions in the publication's recent history. The sweeping reduction followed months of subscriber departures after the newspaper declined to endorse a presidential candidate during the 2024 election cycle.

Prior to the layoffs, Bezos had directed the Post's opinion section to emphasize "two pillars: personal liberties and free markets." The departure of Will Lewis, the newspaper's publisher and CEO who had received a $3 million annual salary, followed shortly after the staff reductions, though the circumstances surrounding his exit remain partially undisclosed.