Jeff Bezos and Donald Trump were once adversaries, with Bezos even suing the Pentagon in 2019, alleging that Trump's animosity toward The Washington Post cost Amazon a $10 billion contract. But recently, Bezos has made a sharp public reversal, cozying up to Trump in ways that have shocked his close associates and the Post’s newsroom. This includes killing the Post's endorsement of Kamala Harris, backing content that aligns with Trump's views, and even investing in a Melania Trump documentary. While some insiders argue Bezos is simply protecting his business empire—especially his space venture, Blue Origin—others believe he’s acting out of frustration with the Democrats’ regulatory stance against Big Tech. As one adviser put it: “You want to know why Jeff has changed? It is part practicality driven by fear, mixed with a little opportunism.” Whatever the reason, his pivot has fueled internal turmoil at The Washington Post, with veteran journalists leaving in protest and Trump himself expressing approval of Bezos' recent actions.

Key Points:

• From Adversary to Ally: Bezos initially fought with Trump, even suing over a lost $10 billion government contract, but has now taken a friendlier stance.
• Strategic Business Calculations: Some believe Bezos is aligning with Trump to protect Amazon, Blue Origin, and his other ventures from government pressure.
• Frustration with Democrats: Bezos reportedly resents the Biden administration’s strict regulations on Big Tech, which may have influenced his shift.
• Amazon’s Pro-Trump Moves: Amazon has funded a Melania Trump documentary, streamed episodes of The Apprentice, and donated $1 million to Trump’s inauguration.
• Washington Post Turmoil: Bezos has interfered with editorial decisions, killing a Kamala Harris endorsement and shifting the paper’s focus, which has led to high-profile resignations.
• Trump’s Approval: The former president has acknowledged Bezos’ transformation, saying he now sees The Washington Post as being run properly.
• Blue Origin’s High Stakes: Bezos' space venture competes with Elon Musk’s SpaceX for lucrative government contracts, making good relations with Trump crucial for its survival.
• A Smart Financial Move?: One associate described Bezos' strategy as “offering money to buy the Trump family’s affection,” calling it a calculated investment.

Bezos' pivot from political foe to strategic ally of Trump reflects the immense stakes involved in modern business and politics. Whether it's about survival or shifting ideology, one thing is certain—Bezos is playing a high-stakes game that has upended both his newspaper and his broader corporate empire.
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