At the end of a day that had seen President Donald Trump spend plenty of time on Twitter, Trump had one final flurry of tweets to lob at a familiar target: Amazon (AMZN) CEO and Washington Post-owner Jeff Bezos.
“So many stories about me in the @washingtonpost are Fake News,” Trump tweeted. “They are as bad as ratings challenged @CNN. Lobbyist for Amazon and taxes?”
Clarifying the rhetorical question posed at end of his previous tweet, Trump added: “Is Fake News Washington Post being used as a lobbyist weapon against Congress to keep Politicians from looking into Amazon no-tax monopoly?”
Bezos has at various times over the last couple years been a target of Trump’s ire. Through his personal investment vehicle, Bezos Expeditions, the Amazon CEO purchased The Washington Post for $250 million in 2013.
And while Bezos, unlike his tech CEO peer Mark Zuckerberg of Facebook (FB), has displayed no signs of political ambitions, his wealth and influence in American business and culture is perhaps only eclipsed by the influence enjoyed by the office of the presidency.
With Trump’s approval rating currently sitting near 40% and some reports showing more than half of U.S. households are subscribers to Amazon’s Prime membership service, the view of Bezos among the American public is likely more favorable than the current president.
And if there’s one thing we know about Trump, it’s that Bezos’ popularity gap — perceived or otherwise — will annoy him to no end. (Trump, for example, is still re-litigating the election because, despite his winning the Electoral College in a landslide, he lost the popular vote to Hillary Clinton.)
Trump’s most recent tweets are part of a running criticism Trump has made of The Washington Post and the paper’s billionaire owner. Trump’s recent characterization of The Post as “Amazon Washington Post” also implies that Bezos is ordering the paper to pursue unfavorable coverage of the administration.
The Post famously broke the existence of the Billy Bush tape in which Trump used lewd language to describe interactions with women.
The president has also often sought to tie-in Bezos’ position at the top of Amazon with his ownership of the Post.
These businesses, however, are unrelated — Amazon is a public company Bezos has a large ownership stake in and also runs; The Washington Post is wholly-owned by Bezos’ personal investment fund and he does not have a day-to-day operational role at the paper.
Amazon is known in the business world for pursuing a strategy of emphasizing free cash flow it can reinvest in its businesses over growing profits at all costs. In 2015, Trump insinuated Bezos was also losing money at The Post on purpose to avoid taxes.
That Amazon for years operated at a loss and that Bezos personally owns The Washington Post have no bearing on each other.
But Trump’s distaste for The Post’s reporting and its billionaire owner makes clear that the president sees Bezos as a threat, and perhaps the biggest threat outside of clear political rivals.
#AmazonWashingtonPost
Over the weekend, Trump tweeted, “A new INTELLIGENCE LEAK from the Amazon Washington Post, this time against A.G. Jeff Sessions. These illegal leaks, like Comey’s, must stop!”
This tweet followed one sent in late June by Trump which said, “The #AmazonWashingtonPost, sometimes referred to as the guardian of Amazon not paying internet taxes (which they should) is FAKE NEWS!”
That outburst led to a number of follow-up questions — What are internet taxes? Has anyone ever used the hashtag AmazonWashingtonPost? And could Trump actually look to step-up regulatory oversight of an online retailer like Amazon?
On the regulatory front, Trump’s clear distaste for both The Post and its owner presents a potentially interesting showdown between the regulators and Amazon.
Earlier this month, Yahoo Finance’s Dan Roberts outlined how Amazon could potentially face increasing scrutiny from regulators as it enters more and more markets. The company, for example, announced it would buy Whole Foods for about $14 billion, its biggest acquisition ever and its first major step into the grocery space.
Roberts noted, however, that while Amazon’s influence is huge across a number of markets — media, retail, web services, shipping — it doesn’t have an unfair majority in any of them. In other words, despite Amazon’s vast size it doesn’t have a monopoly standing that would offer customers a worse deal.
On the Whole Foods front, Yahoo Finance’s Erin Fuchs reported that Amazon will likely get approval for the deal, even if the FTC finds the company deceived customers about pricing discounts.
Moreover, the business community has viewed the Trump administration’s pledge to cut regulation as perhaps the most concrete good the president can do for the economy. Using the weight of government to pressure Amazon would be in conflict with the stated aims of a White House focused on helping American business as much as anything else.
Bezos and Trump go way back
Trump’s history with Bezos — who along with other tech leaders has met with Trump both at The White House and Trump Tower — goes back to his time as a candidate in a crowded GOP field.
In December 2015, when Trump was one of 14 candidates in the GOP presidential primary — a field that still officially included the likes of Senator Lindsey Graham (R-SC), former New York governor George Pataki, and former HP CEO Carly Fiorina — he for the first time took aim at the Post and its owner.
“The @washingtonpost, which loses a fortune, is owned by @JeffBezos for purposes of keeping taxes down at his no profit company, @amazon,” Trump tweeted.
Just a few minutes later, Trump added in a follow-on tweet that, “The @washingtonpost loses money (a deduction) and gives owner @JeffBezos power to screw public on low taxation of @Amazon! Big tax shelter.”
(Earlier in 2015, before entering the presidential race, Trump tweeted a link to a story critical of the Post’s coverage of Trump. In May of 2015, also before entering the race, Trump called then-Washington Post editor and current CNN personality Chris Cillizza a “moron.”)
Bezos later that same day tweeted, “Finally trashed by @realDonaldTrump. Will still reserve him a seat on the Blue Origin rocket. #sendDonaldtospace.” (Blue Origin, like the Washington Post, is a rocket company owned by Bezos through his Bezos Expeditions investment fund.)
In January 2016, Trump tweeted that, “The tax scam Washington Post does among the most inaccurate stories of all.”
If history is any guide, then, it seems unlikely Trump will ever get past whatever it is about Bezos — his newspaper, his retail company, his fortune — that bothers the president so much.
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Myles Udland is a writer at Yahoo Finance. Follow him on Twitter @MylesUdland
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