President Donald Trump has been a vocal critic of Amazon in general and of CEO Jeff Bezos in particular - as well as The Washington Post, the Bezos-owned newspaper that has published much reporting critical of the president.
That history is at the center of reports indicating that Trump's opposition to Amazon went as far as the bidding process for the Pentagon's $10 billion Joint Enterprise Defense Infrastructure contract, which the Amazon Web Services cloud-computing division was the favorite to win but did not.
Trump reportedly wanted to "scuttle" the JEDI bidding process earlier this year over concerns that Amazon would get the deal. Even before that, a coming book says Trump last year ordered former Defense Secretary James Mattis to "screw Amazon" out of the contract. Indeed, back in August, Sen. Mark Warner, the Virginia Democrat, raised concerns that Trump was seeking to use his power to punish the media.
So when the Department of Defense announced Friday that Microsoft had scored the JEDI contract, the immediate reaction of many observers was to assume that the huge upset over AWS had everything to do with Trump.
Several industry experts and Wall Street analysts, however, say they believe that any Trump factor in the JEDI decision was overrated and that all signs point to Microsoft having won the deal on its own merits as a heavy hitter in cloud computing.
"I hesitate to say that Trump was the reason behind Amazon not winning this," James Bach, a federal spending analyst at Bloomberg LP, told Business Insider. "Microsoft was more than capable of winning this without any kind of influence."
At the same time, Bach said, it's definitely "atypical" for a president to get involved with this kind of government procurement contract.
Daniel Newman, the founding partner and principal analyst at Futurum Research, told Business Insider that Trump's involvement with the deal did cast questions over the final result.
"You have two very, very sound companies, and then you have all these extraneous factors like Trump," Newman said, adding: "It's really disappointing that we couldn't see an award made strictly based upon what solution offered the best technology to meet the needs."
Still, several of the experts we spoke with said Microsoft, with its Azure cloud platform, was more than up to the task of helping the Pentagon modernize its IT infrastructure.
"They had not only infrastructure that could take on Amazon's but they also had experience working in this legacy IT environment, so it makes sense that the DOD might choose Microsoft for that, because Microsoft has this ability to do the next-gen IT migration and at the same time help them manage and rationalize their legacy footprint," Bach said.
While Microsoft lacked the necessary capabilities to qualify for JEDI at the outset of the bidding process, experts said the company had made great strides in closing its technology gap with Amazon Web Services while making itself more attractive to customers in regulated industries like the public sector.
"MSFT has worked hard to appeal to late adopting industries, such as government, healthcare, financial institutions," Oppenheimer analysts said in a note to clients on Sunday. "MSFT has been prudent in gaining compliance/governance certifications and improving security to win over these late adopters."
Regardless of whether Trump played a role in the JEDI procurement process, some experts said politics might still have factored into the decision to award it to Microsoft.
Putting aside Trump's personal stance, Amazon has come under fire from key Democrats like Sen. Elizabeth Warren, a presidential candidate who has said tech titans like Amazon wield too much power and should be broken up.
"Politics likely played a key role as AMZN has been under government scrutiny from both the left and right," the Oppenheimer analysts said of the JEDI deal.
Additionally, Amazon's relationships with the Department of Defense have been somewhat strained after the company spent much of the past year fending off a lawsuit from Oracle over the JEDI award process, Christopher Cornillie, a federal technology market analyst at Bloomberg Government, told Business Insider.
That court battle, he said, "made everyone aware of how aggressively Amazon was pursuing federal contracts."
He continued: "They spent millions a year on lobbying and strategically hired a number of former government officials they believed would give them an edge in upcoming procurements. This was on display with JEDI."
It's unlikely that the JEDI story ends here for Amazon.
Amazon on Friday was " still evaluating options," a person familiar told Business Insider. The Wedbush analyst Daniel Ives said in a note to clients on Friday that his firm "fully" expected Amazon "and others" to challenge the JEDI decision in court.
Oddly enough, however, at least one expert thinks the shadow of Trump over the JEDI deal may actually end up helping Amazon Web Services in the long run. At least some arms of the government might feel a need to show that they're willing to choose the best technology, no matter where it comes from.
"That could mean that any government project that Amazon pursues might be similarly affected by Trump's dislike," Charles King, the president and principal analyst of Pund-IT, told Business Insider. "But it might also lead other agencies to treat Amazon leniently in order to demonstrate that they aren't being inappropriately swayed by the president."
Another silver lining, King said, is that even the possibility that there was a political motive for giving JEDI to Microsoft might actually "lend weight to whatever efforts that AWS might make to reverse or appeal the contract being awarded to Microsoft."
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