A dinner between Donald Trump and Amazon founder Jeff Bezos is the latest development in their history, which has seen both men criticize each other publicly.

Bezos has spoken out against Donald Trump in the past — and vice versa. However, Bezos has changed his tune on the president-elect, saying he is feeling optimistic now about Trump’s return to the Oval Office.

Speaking at The New York Times’ DealBook Summit last week, Bezos said he’s “actually very optimistic” about another Trump term.

“What I’ve seen so far is he is calmer than he was the first time and more settled,” he said. “You’ve probably grown in the last eight years. He has too.”

Bezos said he’s also encouraged by Trump’s deregulation aims, which include his newly created Department of Government Efficiency, headed by Vivek Ramaswamy and Elon Musk, a Trump ally and major donor to his campaign.

“He seems to have a lot of energy around reducing regulation. If I can help do that, I’m going to help him,” Bezos said.

Trump, for his part, said in his recent “Meet the Press” interview that he and Bezos are “having dinner.”

Last month, Jeff Bezos congratulated Trump on “an extraordinary political comeback and decisive victory” in the 2024 presidential election, wishing the president-elect “all success in leading and uniting the America we all love.”

Following the assassination attempt on Trump at a Pennsylvania rally in July 2024, Bezos broke a hiatus of nearly nine months on X, formerly known as Twitter, to write, “Our former President showed tremendous grace and courage under literal fire tonight. So thankful for his safety and so sad for the victims and their families.”

The billionaire Amazon founder and Trump have been contentious at times. In 2016, Bezos said Trump’s wish to lock up Hillary Clinton or refuse to accept a loss in that election “erodes our democracy around the edges.”

“One of the things that makes this country as amazing as it is, we are allowed to criticize and scrutinize our elected leaders,” Bezos said at the time.

“An appropriate thing for a presidential candidate to do is say, ‘I am running for the highest office in the world, please scrutinize me,'” he continued. “That’s not what we’ve seen. To try and chill the media and threaten retribution and retaliation, which is what he’s done in a number of cases, it just isn’t appropriate.”

Following Trump’s election that year, Bezos was one of several tech leaders who met with the president-elect in a summit Bezos later described as “very productive.” Introducing himself in the meeting, Bezos added that he was “super excited about the possibilities this could be the innovation administration.”

Trump and Amazon

While campaigning for the 2016 presidential election, Trump said Amazon would have “such problems” if he became president.

In 2017, he tweeted that the company was “doing great damage to tax paying retailers” and that “towns, cities and states throughout the U.S. are being hurt.”

He repeated similar sentiments the following year, saying that Amazon was pushing smaller retailers out of business.

Trump has also said on multiple occasions that Amazon should be paying more for USPS deliveries.

“Why is the United States Post Office, which is losing many billions of dollars a year, while charging Amazon and others so little to deliver their packages, making Amazon richer and the Post Office dumber and poorer?” he tweeted in 2017. “Should be charging MUCH MORE!”

In 2019, Amazon filed a federal complaint challenging the Department of Defense’s decision to award Microsoft a $10 billion contract to move sensitive data to a cloud server rather than Amazon Web Services.

The company said in the complaint that Trump swayed the decision to “pursue his own personal and political ends” and to harm Bezos, “his perceived political enemy.” Amazon said Trump made “repeated public and behind-the-scenes attacks” about the company and Bezos, who was still CEO at the time.

In 2021, the DoD canceled the contract with Microsoft and announced a multi-vendor contract to seek proposals from Microsoft and AWS as “the only Cloud Service Providers (CSPs) capable of meeting the Department’s requirements.”

Trump and The Washington Post

Trump has repeatedly criticized The Washington Post, which Bezos owns.

In 2019, Trump bashed Bezos and the Post as he appeared to talk about Bezos’ divorce from MacKenzie Scott.

“So sorry to hear the news about Jeff Bozo being taken down by a competitor whose reporting, I understand, is far more accurate than the reporting in his lobbyist newspaper, the Amazon Washington Post,” Trump wrote on X. “Hopefully the paper will soon be placed in better & more responsible hands!”

For the first time in decades, the newspaper didn’t publish an endorsement of a presidential candidate in 2024. Bezos reportedly intervened to block an endorsement of Kamala Harris that had already been drafted.

Bezos later wrote an op-ed defending the newspaper’s decision to decline to endorse, saying endorsements “create a perception of bias” and “do nothing to tip the scales of an election.”