Jeff Bezos reportedly told President Trump that the Washington Post was his worst investment, according to a book by New York Times journalists Jonathan Swan and Maggie Haberman titled, “Regime Change: Inside the Imperial Presidency of Donald Trump.”

Bezos told Trump that the people at the Washington Post were “terrible” and refused to listen. “They don’t listen. My other companies, they listen,” Bezos told Trump during a December 2024 dinner, according to the book. Bezos was reportedly frustrated after the publication lost more than $100 million in 2025.

Around two months after the dinner, Bezos ordered the Post to move in a new direction, promoting the pillars of personal liberties and free markets. Bezos also withheld the endorsement of Kamala Harris, prompting backlash from subscribers of outlet, according to the book. 

Trump and Bezos have a tumultuous past, with Trump saying in an interview for the book that he “hated” Bezos during his first term under the belief that the billionaire directly controlled what the paper printed. Now, the pair have a much more congenial relationship, with Bezos being among the billionaires who attended the president’s inauguration.

Bezos’ newly found, cozier relationship was described by Swan and Haberman as part of a larger push by Big Tech to cozy up to the president.

The report comes after the Washington Post fired a third of its workforce in February. The move was dubbed “a strategic reset” to ensure competitiveness in the age of artificial intelligence. The publication completely dismantled its sports desk and drastically shrank its international desk.

The cuts marked one of the most significant restructurings in the newspaper’s modern history and underscored the financial pressures facing legacy media organizations. The changes also fueled concerns among journalists and media observers about the future direction of the publication under Bezos’ ownership and whether its editorial identity would continue to evolve amid mounting economic challenges.