MANDEL NGAN/AFP via Getty Images; Erin Schaff/Getty Images
- Jeff Bezos used to test the Echo Show by asking Alexa to play videos making fun of Donald Trump.
- Bezos and Trump have long been at odds, stemming from Bezos' ownership of the Washington Post.
- Trump also criticized Amazon over matters like the USPS and its attempt to win the JEDI contract.
- See more stories on Insider's business page.
Amazon CEO Jeff Bezos and former President Donald Trump have never exactly seen eye-to-eye. And while Trump's animosity toward Bezos was more public, it appears that Bezos, too, poked fun at Trump behind closed doors.
Brad Stone's new book, "Amazon Unbound: Jeff Bezos and the Invention of a Global Empire," chronicles much of Amazon's last decade, including Amazon's shift into new product categories, like the Amazon Echo. Bezos was the mastermind behind the creation of the Echo and its built-in virtual assistant, Alexa, and was hands-on in the testing process for new devices – including the Echo Show, Amazon's first Echo with a video screen, in 2016.
According to Stone, Bezos demoed a prototype Echo Show on multiple occasions and would ask Alexa to play videos that mocked Trump: "Alexa, show me the video, 'Donald Trump says "China,'" and "Alexa, play Stephen Colbert's monologue from last night."
A vice president who was at the demos told Stone that Bezos would then "laugh like there's no tomorrow."
'I'm an inexperienced trash talker but I'm willing to learn. :)'
Bezos' and Trump's animus toward one another extends at least a year earlier, to the winter of 2015, when Trump began tweeting about the Washington Post, which Bezos purchased for $250 million in 2013. Trump tweeted that Bezos only owned the paper to keep "taxes down at his no profit company, @amazon," adding in a follow-up tweet that the Post is a tax shelter. (There's no evidence to support these claims, and Bezos' ownership of the post is separate from his role at Amazon.)
According to Stone, Bezos emailed his senior vice president of corporate affairs, Jay Carney, later that morning with the subject line: "Trump trash talk."
"Feel like I should have a witty retort. Don't want to let it go past," Bezos wrote, according to emails obtained by Stone. "Useful opportunity (patriotic duty) to do my part to deflate this guy who would be a scary prez. I'm an inexperienced trash talker but I'm willing to learn. :)"
Carney recommended that Bezos say nothing back, but Bezos still wanted to engage with Trump, eventually responding with a tweet that offered to reserve Trump a seat on a Blue Origin rocket, also owned by Bezos, and included the hashtag "#sendDonaldtospace."
A spokesperson for Amazon declined to comment on Bezos and Trump's relationship.
Trump and Bezos clashed several more times during Trump's presidency
The squabble would play a role behind the scenes during several high-profile incidents in Bezos' personal and professional lives.
In January 2019, Bezos announced his divorce from his wife of 25 years, MacKenzie - soon after, his affair with TV host and helicopter pilot Lauren Sanchez was outed by the National Enquirer. The ensuing tabloid scandal led to speculation that there were political motivations behind publishing the story: David Pecker, then the publisher of Enquirer-owner AMI, is a longtime Trump ally.
Trump's antipathy toward Bezos would impact Amazon's business dealings as well. Trump alleged in 2018 that Amazon was hurting the US Postal Service by not paying it enough to deliver packages, a claim he repeated several times over the years. Amazon produces billions in revenue for USPS, according to documents that leaked last year.
Trump later became involved in the competition between Amazon, Oracle, Microsoft, and others to secure a lucrative Department of Defense contract known as JEDI. Trump spoke publicly about complaints he was hearing about Amazon, and Trump's son, Donald Trump Jr., called Amazon "shady and potentially corrupt" in a tweet about the situation.
Microsoft ultimately won the $10 billion contract in 2019, and Amazon has publicly stated that it believes Trump's "repeated public and behind-the-scenes attacks" against Amazon and Bezos are the reason it wasn't awarded the contract.
Amazon later challenged the decision in federal court, and the ongoing litigation may now result in the Pentagon pulling the contract altogether.