Bezos responded with measured firmness. Trump’s threats were “not an appropriate way for a presidential candidate to behave,” he told Baron in a public interview. Throughout the first term, Bezos remained an admirable if inscrutable owner.
The newsroom rewarded his restraint. It broke the news about Trump’s Access Hollywood tape and continued reporting aggressively, exposing lie upon lie, grift upon grift. Bezos never tried to alter coverage, even when it came at a cost to Amazon. He followed the example of the Post’s legendary publisher Katharine Graham, who stood up to pressure from the Nixon administration through both the Pentagon Papers showdown and Watergate.
Trump didn’t succeed in punishing Bezos on postal rates, taxes, or antitrust. Where he was able to hurt him was on Amazon’s bid to build JEDI, the Joint Enterprise Defense Infrastructure, a winner-take‑all $10 billion contract to move all of the Defense Department’s data to a centralized cloud. The program was supposed to allow the Pentagon to communicate more effectively with battlefields and to make greater use of AI. In July 2019, Trump said he might intervene in the decision. A few months later, the award went to Microsoft Azure over Amazon Web Services, which was widely seen as the market leader in cloud computing and the technical favorite.
People joked that buying the Post hadn’t cost Bezos $250 million—it had cost him $10.25 billion.
In early 2019, the midlife reinvention that had made Bezos so visibly swole collided with tabloid politics. On January 9, he and MacKenzie announced their divorce after twenty‑five years of marriage—hours before the National Enquirer published details of Bezos’s relationship with Lauren Sánchez.
The divorce that followed was orderly and unusually civil by plutocrat standards. In April 2019, MacKenzie Scott received 25 percent of the couple’s Amazon shares (and granted Jeff voting control over them). She took no stake in Blue Origin or the Post. She promptly committed herself to large‑scale philanthropy, pledging to give all of her money away.
Jeff wanted to spend more of his. He commissioned a 417‑foot sailing yacht that would be the largest in the world. He called it the Koru, a Māori term for an uncoiling fern, with the symbolic meaning of new life and growth. The ship’s figurehead, a voluptuous goddess with feathery wings, appeared to depict a blend of a Norse deity and his pneumatic fiancée.
While Bezos was remaking his personal life, Elon Musk was opportunistically aligning himself with power. In May 2024, Musk met with Trump in Palm Beach and reportedly discussed an advisory role in his future administration. Then, minutes after a would‑be assassin’s bullet grazed Trump’s ear at a Pennsylvania rally, Musk endorsed him outright and began donating immense sums to his campaign.
After Trump won the election, Musk—now in the catbird seat—moved to protect his position by advising Trump that Bezos was not his friend.
Facing this array of risks, Bezos began doing what nearly every other tech leader was doing: making nice with the Trump Family.
