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Amazon’s bid to build the Pentagon’s war cloud has been mired in accusations of favoritism since the beginning. But a new ProPublica investigation reveals how close Amazon and its CEO Jeff Bezos have been to the project since its inception.

It’s the latest sign that Amazon’s chances of landing the $10 billion contract could be in jeopardy as its cloud rival Microsoft continues to compete for the coveted project.

Background: Amazon and Microsoft are the last contenders for the $10 billion, 10-year contract to migrate the Pentagon’s data to the cloud. The project — known as Joint Enterprise Defense Infrastructure (JEDI) — is a massive overhaul of the Defense Department’s technology infrastructure that will allow different branches of the military share sensitive information in the cloud and incorporate artificial intelligence technology. The Pentagon was expected to announce a winner this summer but the timeline is delayed following new inquiries into Amazon’s role in the procurement process.

What’s new, according to ProPublica’s investigation:

  • The Pentagon called off an unorthodox swearing-in ceremony that would have given Bezos a spot on the military’s Defense Innovation Board in August 2017. Then-defense Secretary Jim Mattis was forced to cancel the event when an employee sounded the alarm over Bezos’ failure to complete the requisite background check.
  • Bezos and Mattis had a private meeting in lieu of the swearing-in ceremony in which the Amazon CEO made the case for migrating the Pentagon’s data to the cloud.
  • Bezos and Mattis met again in January 2018 at a Washington D.C. restaurant as DoD was finalizing the draft bid criteria for JEDI. They were joined by Mattis’ aid Sally Donnelly, a former outside strategist for Amazon, as well as an Amazon government-sales executive.
  • A similar relationship was established with former Google CEO Eric Schmidt, who was appointed to the Defense Innovation Board under President Barack Obama. Google won a $17 million subcontract to improve the military’s image recognition software following a trip in which Schmidt remarked on the outdated technology the military was using.

What Amazon and DoD say: Amazon did not immediately respond to GeekWire’s request for comment on the report. An Amazon spokesperson told ProPublica that the company did not know Bezos needed a security clearance to join the DoD board. Amazon said accusations of favoritism were misinformed or motivated by animus from companies, like Oracle, that were cut from the JEDI contest early on.

Update: DoD spokesperson Elissa Smith said, “Mr. Bezos’ choice pertaining to a security clearance is a personal matter and out of respect for his privacy, the department cannot comment, and would defer to Mr. Bezos.” She also noted Bezos was not nominated to the Defense Innovation Board “for a variety of reasons.”

In context: The tight relationship between the Pentagon and tech industry isn’t new. The Defense Department is part of Silicon Valley’s origin story. Defense contracts following World War II transformed the sleepy region into the center of the tech universe it is today.

Big picture: Amazon was once seen as a shoo-in for JEDI but the mounting accusations of favoritism could make its chances murkier. President Donald Trump, a frequent critic of Amazon and Bezos, told reporters last month he was “getting tremendous complaints about the contract with the Pentagon and with Amazon … they’re saying it wasn’t competitively bid.” A few weeks later, his new defense secretary, Mark Esper, launched a review of the procurement process, delaying the conclusion of the contest. If the review finds misconduct, it could bolster Microsoft’s chances of winning JEDI or DoD could change its parameters to allow multiple vendors to provide cloud services to the Pentagon.

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