Historians will debate the unique legacy of President Donald Trump for centuries. For the data center sector, his impact is a little clearer: It will be felt in his accidental destruction of one of the world's largest cloud contracts.

To be fair to Trump, JEDI was always a bad idea. From the start of procurement process, proponents were never able to fully explain why the Joint Enterprise Defense Infrastructure contract would go to one company.

Surely, critics said, putting nearly the entirety of the world's largest military's IT needs into the hands of one company was misguided? Instead, they said, the Department of Defense should use the best cloud providers for different parts, and avoid vendor lock in.

Loose lips sink contracts

JEDI That's No Moon.png
– Sebastian Moss/Disney

In 2018, the DoD played down such concerns, claiming the 10-year contract had a review after two years - although it is highly unusual for the department to change providers during these reviews, and would have required a lot of work.

Then there's the fact that JEDI seemed to be written just for Amazon. There's some potentially innocent reasons for this: AWS has been the market leader since the start of the cloud race, has provided cloud services to groups like the CIA since 2013, and knows how to work with the military. It stands to reason that it could check all the boxes on any cloud procurement process.

Others saw nefarious hands at work. Oracle filed a protest with the Government Accountability Office in 2018 arguing that the contract was “designed around a particular cloud service," and was soon followed by IBM.

A Washington contract investigator, RosettiStarr, began sending journalists dossiers claiming that Sally Donnelly, a former outside consultant to Amazon, was using her position at the Pentagon to favor the company. Its backer was never revealed.

Then Oracle said that a former project manager for the contract, Deap Ubhi, had worked for Amazon prior to his time at the DoD, and then went to work for them afterwards. He also considered selling a business to AWS, and allegedly exchanged derogatory messages with his colleagues about competitors and DoD members considering other vendors than AWS.

The company later also targeted Anthony DeMartino, the chief of staff for the Deputy Secretary of Defense. The company claims that he was involved in discussions about the contract for a period of six months, touting a single vendor approach, whilst simultaneously providing consultancy services to AWS.

Oracle has filed multiple lawsuits, protests, and appeals. So far, investigations by the DoD and General Accountability Office have said that there were errors in the procurement process, but that none of the people with conflicts of interest impacted the process in any meaningful way.

Behind the scenes, Oracle was engaging in an aggressive shadow war, drafting its vast lobbyist army, as well as turning to 'thought leaders,' thinktanks, and off-the-record conversations to try to convince lawmakers and journalists that something fishy was going on.

When Oracle lost the first of its many court cases, Senator Marco Rubio penned an open letter attacking the contract and how it looked like it would go to AWS. Rubio received $4m in campaign donations from Oracle founder Larry Ellison in 2016 alone.

Then there's Trump. He had been told about Oracle's concerns by co-CEO and Trump transition team member Safra Catz over dinner in 2018, and spoke to Rubio about it following the letter.

Throughout the process, reports swirled that he might cancel the contract, and he called for an investigation into it. Trump was “obsessed with Amazon," five sources told Axios.

We didn't need an anonymous source to see that: Trump repeatedly tweeted falsehoods about how Amazon cheats the post office, and said that Amazon used the Washington Post to lower its tax bill (the company doesn't pay much tax, but that's not why).

The Post, which covered his foibles aggressively, is wholly owned by Jeff Bezos, Amazon founder and then-CEO. Trump made it clear he was not a fan of the paper, nor of the man

"[Trump] gets obsessed with something, and now he’s obsessed with Bezos," a source told Vanity Fair at the time. "Trump is like, how can I f**k with him?”

In a major lobbying coup, Oracle managed to get a document claiming a wide-reaching conspiracy by Amazon and the DoD to Trump's desk. It contained a flow chart titled "A Conspiracy to Create a Ten Year DoD Cloud Monopoly," that suggests that senior military officials were potentially influenced by money.

The chart includes images of two secretaries of Defense, Ash Carter (pictured alongside President Obama) and James Mattis, along with representations of dollar signs, arrows and a heart linking the various figure.

“I’m getting tremendous complaints about the contract with the Pentagon and with Amazon," Trump told reporters at the time.

"They’re saying it wasn’t competitively bid... Some of the greatest companies in the world are complaining about it, having to do with Amazon and the Department of Defense, and I will be asking them to look at it very closely to see what’s going on."

That same week, he retweeted a Fox News segment called 'The Bezos Bailout.' Host Steve Hilton said: "President Trump is demanding more information on the JEDI contract and is considering intervening - quite right too. Draining the swamp means stopping this contract... It's not just appropriate, but vital that the President kills this contract...

"Mr President, if you want to keep draining the swamp, don't let the Bezos bailout fill it back up."

Amazon responded by expanding its lobbyist team, hiring Jeff Miller, one the bundlers that helped Trump campaign raise funds for its reelection effort.

At the time, his company, Miller Strategies, employed two alumni of the Trump administration - Ashley Gunn, a former special assistant to the president, and Jonathan Hiler, a prior Director of Legislative Affairs for Vice President Mike Pence.

These lobbyists spent their time pushing back against criticism of JEDI, efforts to cancel the contract, and claims that it shouldn't be single source.

Then Microsoft won.

Change of plan!

Suddenly, surprised Amazon lobbyists and PR people shifted tactic: JEDI had to be stopped.

The company now claims that it lost out because of "blatant political interference" from Trump, pointing to a claim by Guy Snodgrass, a speechwriter for former Defense Secretary Jim Mattis, that said Trump called the secretary telling him to "screw Amazon" out of the deal.

"The stakes are high," Amazon said at the time. "The question is whether the President of the United States should be allowed to use the budget of DoD to pursue his own personal and political ends."

By 2020, Amazon had successfully won an injunction on the contract - meaning that the DoD could not start using Microsoft Azure's JEDI until the whole case is concluded.

That case is still ongoing, and - prior to JEDI's death - Amazon was seeking to depose senior White House officials, including potentially Trump.

Such a lengthy, and embarrassing, case risked delaying the military's digital transformation to the point it was becoming a security risk. As time dragged on, killing JEDI became inevitable.

It is hard to know how much Trump's public and private animosity towards Bezos played in it losing JEDI. An investigation by the Department of Defense Inspector General cleared the military's decision - but that doesn't mean much, as it was not able to fully investigate White House interference "because of the assertion of a 'presidential communications privilege.'"

What is clear, however, is that such a large and controversial contract was always going to face some legal challenges.

But with the President publicly talking about a procurement process and trashing one of the applicants, it was inevitable that he would create enough fodder for Amazon lawyers to keep a case going for years.

JEDI was doomed from the minute it got on Trump's radar.

Ironically, that might prove a boon for Amazon. It had lost out on JEDI entirely, but now it can compete again for the reworked Joint Warfighter Cloud Capability, a multicloud procurement process featuring just AWS and Microsoft Azure.

Sometimes it pays to have enemies.

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