In 2016, Jeff Bezos worried aloud that Donald Trump, then an underdog presidential candidate, could “erode” American democracy.

Speaking at a Vanity Fair summit in October that year, Bezos said Trump’s campaign tactics threatened the country’s commitment to freedom of speech and showed his inability to be scrutinized, something Bezos said was crucial for those running for the country’s highest office. Bezos pointed to Trump’s statements that he may not concede if he lost and that, if he won, he would “lock up” his opponent, Hillary Clinton.

With pledges to fight climate change and fund preschools, Bezos was deemed by some critics to be a “woke” capitalist, even as Amazon employees pushed the executive to do more for the environment and Amazon’s workers.

Now, as Trump returns to the White House, the tech mogul has changed his tune in a shift that could have far-reaching consequences for the businesses attached to his name: Amazon, Bezos’ rocket company Blue Origin and The Washington Post, which Bezos bought in 2013.

Bezos is following the same playbook as many tech executives— including Microsoft’s Satya Nadella, Google’s Sundar Pichai, Meta’s Mark Zuckerberg and Apple’s Tim Cook — hoping to gain favor and avoid backlash from the incoming administration with phone calls, visits and donations, business professors and industry-watchers told The Seattle Times.

That connection to the White House may be particularly important for Bezos and Amazon, which felt the impact of Trump’s disdain during his first administration.

Trump often criticized coverage in The Washington Post, attacking Bezos personally for critical reporting, and accused Amazon of failing to pay enough taxes. In 2019, Amazon accused the government of unfairly cutting it out of a lucrative defense contract because of Trump’s bias.

Tech executives learned a lot from Trump’s first term, said Adam Kovacevich, founder of the tech policy coalition Chamber of Progress. The best way to connect with the president is to bond over a shared enemy. Trump responds more to personal relationships than those who are cozying up to his aides and others in his orbit.

And, most of all, he likes to be wooed.

Kovacevich, who believes Bezos’ relationship with Trump didn’t stand apart from the president’s connection to any other executive, said “Trump really is flattered by attention from big company CEOs.”

“What you see right now is each company trying to build a CEO-level direct line of contact to Trump,” he said.

At a New York Times event last month, Bezos said he was “optimistic” about a second Trump presidency. In July, Bezos praised Trump's behavior after an assassination attempt at a campaign rally, publicly congratulated him on an “extraordinary political comeback” in November, and visited Trump’s Florida resort in December.

Amazon, where Bezos still serves as executive chairman, donated $1 million to Trump’s inauguration fund and will stream the Monday event on its Prime Video service. It also recently announced it would distribute an upcoming documentary on soon-to-be first lady Melania Trump.

Amazon CEO Andy Jassy, who took over after Bezos stepped down in 2021, congratulated Trump on a “hard-fought victory” after the election in November. Neither Jassy nor Bezos posted similar congratulations following Biden’s 2020 election. Executives from Blue Origin met with Trump in October.

Then there’s The Washington Post. The paper declined to endorse a candidate in last year’s presidential election, bucking decades of tradition and prompting some staffers to resign. The paper’s editorial staff had reportedly planned to endorse Trump’s opponent, Vice President Kamala Harris.

In January, Washington Post cartoonist Ann Telnaes resigned after the paper rejected her drawing of media executives and tech moguls, including Bezos, bowing before Trump.

The Washington Post’s publisher and Bezos have said those decisions were not political. In an October message defending the paper’s decision, Bezos wrote: “You can see my wealth and business interests as a bulwark against intimidation, or you can see them as a web of conflicting interests. Only my own principles can tip the balance from one to the other.”

While some experts view Bezos’ recent actions as par for the course — it’s normal for executives to curry favors from politicians, no matter who is in charge at The White House — others say the changing dynamic between Trump, Bezos and The Washington Post raises concerns about the freedom of the press.

“Bezos, I’m sure, has some interest in accurate journalism, but his primary interest is economic,” said Marjorie Hershey, a political science professor at Indiana University Bloomington who studies media and elections.

“Because of that, he and a whole lot of other people have apparently decided they’ve got to live through the next four years with Trump so they better not get on his bad side,” Hershey continued. “They’ve essentially capitulated before the battle starts.”

From contrarian to the norm

Having launched Amazon from a Bellevue, Washington, garage in 1994, Bezos is now the second richest person in the world. He ranks behind only Elon Musk, the CEO of Tesla, owner of social media platform X, founder of Blue Origin’s rocket rival SpaceX, and, currently, Trump’s right-hand man.

Robert Lalka, a professor at Tulane University whose book “The Venture Alchemists” documents the rise of Big Tech, said it’s important to put Bezos’ behavior in context of those around him, especially Musk, who spent hundreds of millions of dollars backing Trump and other Republicans in 2024.

Lalka recalled a 2016 interview where Bezos was asked about a $1.25 million donation by venture capitalist Peter Thiel to Trump’s campaign. Thiel, who co-founded PayPal and has provided funding to dozens of startups including LinkedIn and Yelp, was among the few venture capitalists and tech executives to wholeheartedly endorse the presidential candidate in his first campaign, Lalka said.

Bezos, on the other hand, said in 2016, “Peter Thiel is a contrarian. … You just have to remember that contrarians are usually wrong.”

Fast forward eight years and Thiel’s donation pales in comparison to the millions of dollars other tech stalwarts have contributed to Trump while Bezos and other executives have ramped up support for Trump, Lalka said.

“It’s a new era,” he continued. “There’s a lot more going on in terms of trying to make sure you’re in the good graces of the administration.”

Thomas Gilbert, a business professor at the University of Washington, said the change in stance toward the president-elect is all about minimizing surprises for corporate executives — even in an administration prone to volatility.

If Bezos goes to dinner at Trump’s Mar-a-Lago resort, he can then make a call to Amazon’s current CEO or executives at Blue Origin and say ‘“here’s what’s coming and how we should think about,” Gilbert said. “It’s learning from the chaos of the first administration.”

What’s at stake?

While Bezos’ charm offensive may be the Big Tech norm, his philanthropic efforts and stated commitments have often been at odds with Trump's.

Internally, Amazon employees are worried about the former CEO’s turn toward Trump, said Eliza Pan, spokesperson for the worker-led advocacy group Amazon Employees for Climate Justice. Some fear Amazon will “backslide” on prior commitments that now don’t align with Trump’s stated agenda, said Pan, a former Amazon employee.

Amazon Employees for Climate Justice has already accused the company of quietly backing off of some of its climate pledge commitments. And, last week, Amazon halted some of its diversity, equity and inclusion programs, following the lead of several corporations as Republicans increasingly criticize such initiatives.

Amazon has previously said it is “unwavering” in its climate pledge commitment, and said last week it is still working to “foster a more truly inclusive culture.”

Bezos pledged $10 billion through his Earth Fund to fight climate change and Amazon has committed to reach net-zero carbon emissions by 2040. Trump has called climate change a “hoax.”

Bezos and his ex-wife MacKenzie Scott donated millions to organizations helping undocumented immigrants, including one group focused on helping people who are part of the Deferred Action for Childhood Arrivals, or DACA, program. DACA protects undocumented immigrants who came to the United States as children. Trump tried to end the program.

In 2016, Trump said Amazon had a “huge antitrust problem,” and launched an investigation into the company, which continued under President Joe Biden’s term and ultimately resulted in a sprawling antitrust lawsuit. Amazon said it does not act as a monopoly in the e-commerce world.

But for Bezos, government contracts, business-friendly policies and profits are at stake.

“Anytime there’s a change in power, or a change in direction … that’s cause for concern. There’s a lot of ways the government can impact Amazon’s way of doing business and their bottom line,” said Jeffrey Shulman, another business professor at the University of Washington.

Among the most impactful, Shulman said, are changes to corporate tax policy, regulations around artificial intelligence and labor law. Trump could also alter the course of the ongoing antitrust lawsuit against Amazon as he shakes up the Federal Trade Commission, though it’s not clear how far the Trump administration will go. Both outgoing FTC Chair Lina Khan and incoming Chair Andrew Ferguson have said there is bipartisan interest in continuing Big Tech scrutiny.

Blue Origin, meanwhile, is competing with Musk’s SpaceX for government contracts, giving the company’s executive extra incentive to cozy up to the president-elect, said Gilbert, from UW. Bezos is probably thinking, Gilbert said, “I need to not be left in the dust here.”

Trump has promised to impose steep tariffs on foreign goods that could increase costs for Amazon and Blue Origin but many analysts expect Amazon and other large corporations will benefit from Trump’s pro-business, anti-regulation agenda.

Bezos said in December he’s looking forward to it.

Trump “seems to have a lot of energy around reducing regulation,” Bezos said in an interview at a New York Times event after the election. “If I can help him do that, I’m going to help him.”

Pan and Amazon Employees for Climate Justice worry that the last few weeks are a sign of more changes to come.

Even before Trump was inaugurated, "all of this (was) happening,” Pan said. “It’s not just partisan. It’s about seeing that Silicon Valley just wants more power.”

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