A New Pentagon Leader Will Shepherd Controversial JEDI Cloud Award Into Its Final Stretch

Brett Goldstein, a venture capitalist and former Chicago CIO, will replace Chris Lynch as director of Defense Digital Services. The team within the U.S. Digital Service is responsible for the $10 billion winner-take-all cloud computing contract that has embroiled technology heavyweights in a bitter feud.

The Pentagon official who has overseen the JEDI initiative's criteria formation and bidding process is stepping away from leading the team responsible for transforming military IT systems as the hotly contested cloud transformation award comes closer to fruition, the Department of Defense said Tuesday.

Chris Lynch, who started what he thought would be a short stint at the Department of Veterans Affairs almost four years ago, instead took the reins of Defense Digital Services, a team within the U.S. Digital Service established in 2015.

Lynch has shepherded many initiatives over his tenure at Defense Digital Services, but might be most associated with JEDI (Joint Enterprise Defense Infrastructure), which has embroiled technology heavyweights in a bitter feud over the winner-take-all $10 billion cloud computing contract.

[Related: 10 Things You Should Know About The DoD Cloud Strategy]

In a departing letter first reported by fedscoop, Lynch told staff: "JEDI is coming (the nerds have won my friends)."

"And yes, DDS will continue to drive JEDI forward today as we have since the start to better protect the young men and women who keep us safe," Lynch wrote.

Lynch's replacement, Brett Goldstein, will see the controversial procurement process through its final stretch, with a contract anticipated to be awarded no earlier than mid-July to Amazon Web Services or Microsoft Azure.

Goldstein grew OpenTable from its startup phase, then joined the Chicago Police Department after the Sept. 11 terrorist attacks. He eventually became the city's CIO.

Goldstein also co-founded a venture capital firm called Ekistic Ventures and served as an advisor to the U.S. Navy.

Acting Secretary of Defense Patrick Shanahan recruited Goldstein, to whom he will directly report.

"Although we will miss Chris, the unique startup culture he built and the talented team he recruited will continue to disrupt and transform technology at the DoD," Shanahan said in a statement.

Goldstein's "public and private sector knowledge, technical expertise, and commitment to improving government through technology will be invaluable to a range of critical missions across the department."

Goldstein will look to keep recruiting talent from the private sector, the DoD said in a statement.

Those kinds of hires are the source of one of the most contentious issues around JEDI.

In a lawsuit challenging the procurement process, Oracle honed in on two people in particular who helped lead the initiative.

Deap Ubhi served as JEDI project manager at Defense Digital Services after his recruitment from AWS in summer 2016. He returned to AWS as general manager in November 2017.

Anthony DeMartino, chief of staff for the Deputy Secretary of Defense, was a consultant for AWS before being tapped by the DoD.

"While engaged in the JEDI Cloud procurement, Ubhi held discussions with AWS regarding AWS buying one of Ubhi’s businesses, and had employment discussions with AWS," Oracle's complaint alleged.

Ubhi was involved in "highly technical" discussions with JEDI Cloud competitors, including Microsoft and Google, and "drove the single award decision," Oracle alleged. At the same time, Oracle alleged, Ubhi’s messages on Slack shared with other members of the Digital Defense Services team were "riddled with inappropriate comments about competitors, DoD personnel and others, raising significant questions about the propriety of this procurement."

The DoD countered in a memo that made clear Ubhi recused himself from JEDI in October 2017, when discussions with AWS started.

"His access to any JEDI Cloud materials was immediately revoked," the memo read.

DeMartino also advocated "procurement positions, including single source" and participated in JEDI Cloud meetings—in violation of conflict restrictions of the U.S. code, the code of federal regulations and his executive order ethics pledge, Oracle alleged in its filings to the court.

The DoD Standard Of Conduct Office had warned DeMartino not to get involved in any matter involving AWS without prior approval from the office, the complaint stated. But he allegedly ignored the warning and participated in JEDI Cloud discussions for over six months. When he did seek approval, Oracle alleged, the office "directed DeMartino to separate from the JEDI Cloud procurement."

"The procurement damage from DeMartino’s months of involvement had already occurred," Oracle alleged, asking for a full investigation of DeMartino’s involvement before the DoD awards the contract to any company.

Last month, the Pentagon requested Judge Eric Bruggink pause the case so it could further investigate some of the issues raised by Oracle.

The Pentagon recently concluded potential conflicts of interest didn't corrupt the JEDI contracting process, though an Inspector General investigation continues.

Bruggink lifted a stay in Oracle's suit against the federal government and AWS and calendared upcoming filing deadlines in the case.