Bezos Bends the Knee as Tech Billionaires Walk Trump Tightrope

On Monday morning, Punchbowl News reported that Amazon.com would start showing customers how much tariffs are adding to the price of each product. When questioned during a White House press briefing, White House press secretary Karoline Leavitt called the move "a hostile and political act."

Amazon.com later denied the plan, saying that it had been proposed by one of the company's teams but had not received approval. CNN then reported that President Trump personally called Jeff Bezos to complain about the report.

In an afternoon press conference, President Trump confirmed the call.

"Jeff Bezos is very nice," said Trump. "Terrific. He solved the problem very quickly. He did the right thing. Good guy."

Like other tech billionaires, including Mark Zuckerberg, Sundar Pichai, Elon Musk, and Peter Thiel, Bezos has pivoted toward Trump. Whether this is ideological alignment or self-interest is not always clear. The second Trump administration has proven itself quite punitive toward entities it views as adversarial, while Big Tech has demonstrated itself to be politically pliable when financial interests are at stake.

Musk and Thiel have received considerable income through federal contracts; Musk via Starlink and SpaceX contracts, as well as Tesla loans and subsidies, and Thiel through Palantir, which has quickly become a major player in the military-industrial complex, leveraging high-tech surveillance and AI products.

Zuckerberg’s Meta is currently being sued by the Federal Trade Commission, which alleges that it acquired Instagram solely to eliminate a competitor and deliberately made user experiences worse to favor its flagship product. While the FTC has largely been neutered under Trump, this case proceeded despite Meta’s $1 million donation to Trump’s inauguration and its questionable settlement of a $25 million lawsuit that the president had filed against the company, which was largely seen as a gift or even bribe to Trump. According to the Wall Street Journal's reporting, Zuckerberg offered to settle the antitrust case for a fraction of the $30 billion, at just over $450 million, confident that Trump would call off the dogs. The offer was rejected by the FTC.

Bezos has also had a frosty relationship with Trump, stemming from his ownership of The Washington Post, as the President is famously resentful of any outlet that does not shower him with unending praise. WAPO hemorrhaged subscribers after Bezos forced editors to scrap an endorsement of Democratic nominee Kamala Harris in 2024. Bezos then contributed $1 million to the inauguration through Amazon and sparked an even larger subscriber revolt when he announced on X, "We are going to be writing every day in support and defense of two pillars: personal liberties and free markets," alleging "that these viewpoints are underserved in the current market of ideas and news opinion," while noting that "viewpoints opposing those pillars will be left to be published by others." Opinions editor David Shipley resigned immediately.

While Amazon's retail operations remain the primary source of revenue, Amazon Web Services, a major provider of cloud services, generates a substantial amount of operating income and has a growing presence in government contracts. In 2019, AWS protested that it had lost a $10 billion contract with the Pentagon due to Trump’s animus toward Bezos. In 2021, it scored a $10 billion contract with the National Security Agency. Amazon has also expanded into government procurement through Amazon Business, offering bulk purchasing solutions to government agencies. So while the Trump trade war will certainly impact Amazon.com’s bottom line, there is more for Bezos to consider in his relationship with Trump.

Elon Musk, who was the most significant financial supporter of Trump’s 2024 campaign, has fared much better in terms of his companies’ relationship with the administration. As the head of DOGE, Musk was able to cripple regulatory agencies while facing at least $2.37 billion in legal exposure from federal investigations, litigation and regulatory oversight, according to a new report from Senate Democrats released on Monday. The report details a litany of conflicts of interest. Musk has also been accused of using his DOGE position to steer contracts toward Tesla and Starlink.

While the administration hasn’t hampered Musk's companies, his gutting of institutions and employees through DOGE, the Nazi sig heils during Trump’s inaguration, and his support for a right-wing extremist party in Germany have caused significant financial losses for Tesla, with critics dubbing it the Swasticar. As retaliation against Trump’s tariffs against Canada, Ontario Premier Doug Ford announced last month that the province would "rip up" its $100 million Internet contract with Starlink. Musk recently announced he would recede from his role at DOGE to spend more time with his companies. 

After DOGE proved incapable of delivering on its ambitious promises, Musk revised his savings goals from $1 trillion to $150 billion. At the same time, watchdogs have reported that he has only achieved a paltry $12.6 billion in verifiable savings, or, as former Secretary of Labor Robert Reich put it, 0.173% of the federal budget. While DOGE sputters, Trump is significantly expanding the deficit with a record military budget and a plan to make his previous tax cuts, which largely benefit the billionaire class, permanent, more than negating any savings achieved by Musk and company.