Deap Ubhi is a restless guy. At 26, he quit his job in private equity in Northern California, where he had grown up and gone to college, and then moved to India to found Burrp!, a local search site similar to Yelp. He sold the company in 2009 and along with other alums became what they called the Burrp! mafia, seeding and growing other start-ups in India.
“Fast and is extremely straightforward,” one Indian entrepreneur wrote about Mr. Ubhi in an online reference. “Not for the faint of heart.”
After returning to the West Coast, he joined Amazon in 2014 to encourage start-ups to adopt the company’s cloud-computing products. But in less than two years, Mr. Ubhi left to start a company that provided technology to restaurants, inspired by his family’s experience running an Indian-Jamaican-Mexican fusion joint.
He then shifted his career in a new direction, taking his Silicon Valley mentality to the heart of the Washington bureaucracy. He joined a Pentagon effort to recruit techies, and turned the restaurant start-up into a side hustle. He wanted to use his skills not “to make a search engine more performant, or help a box of stuff get to a customer faster; but rather towards service of the American people,” Mr. Ubhi later wrote.
But that circuitous career has landed Mr. Ubhi, now 39, in the center of a Washington drama. The question of what roles he played inside the Pentagon, and when, is holding up one of the largest federal information technology contracts in history. It is a scuffle with an unusual mixture of tech industry rivalries, national politics and the obscure world of government procurement.
The project, a $10 billion deal to bring modern cloud computing to the Pentagon’s arsenal, drew the attention of the biggest tech companies from the moment it was announced in 2017. Amazon, Microsoft, Google, IBM and Oracle all wanted the prize.
But it had a hitch: The contract would go to only one cloud vendor, even though many big companies prefer to work with multiple cloud providers. Amazon, the runaway leader in cloud computing, appeared to be perhaps the only company capable of fulfilling the Pentagon’s huge demands. And that is where Mr. Ubhi’s connections to the company, where he now works again, have thrown a wrench into the process.
The software giant Oracle, which is widely considered ill equipped to land the deal, has aggressively criticized the one-vendor approach. As part of its opposition, the company is arguing in federal court that Mr. Ubhi’s ties to Amazon shaped the contract in the company’s favor.
Before the case was filed last year, the Pentagon found that Mr. Ubhi had no improper influence, and it continued evaluating the proposals despite Oracle’s lawsuit. But in late February, the government said it had received “new information” about Mr. Ubhi that it needed to investigate, essentially delaying the process.
A Pentagon spokeswoman, Elissa Smith, declined to say what new information about Mr. Ubhi had been brought to the department’s attention. The Pentagon had said that the winner of the contract was projected to be announced in April. But Ms. Smith said the inquiry into Mr. Ubhi was “expected to impact the award date.”
Mr. Ubhi, contacted through Amazon, declined to comment, as did the company.
Oracle also declined to comment. But in its lawsuit, Oracle has highlighted Mr. Ubhi’s outspoken enthusiasm for Amazon. In early 2017, he took to Twitter to thank Jeff Bezos, the Amazon founder, for opposing President Trump’s travel ban. “Once an Amazonian, always an Amazonian,” he wrote.
The comments touch on an issue floating around discussions about the contract: whether Mr. Trump would put his finger on the scale. The president’s disdain for Mr. Bezos and Amazon is well documented on his Twitter feed. At a private dinner with Mr. Trump, one of Oracle’s co-chief executives, Safra A. Catz, discussed the contract, Bloomberg reported last year. After that report, the White House press secretary, Sarah Huckabee Sanders, said Mr. Trump was “not involved” in the contracting process.
By the standards of most administrations, it would be extraordinarily unusual for the president to insert himself into the competition for a government contract. But when Mr. Trump was president-elect, he drew attention for taking on Boeing over the cost of a new Air Force One aircraft and pressing Lockheed Martin over the cost of the F-35 fighter jet.
If Mr. Trump went so far as to say “who should compete, or how one company should be evaluated compared to another, that would be a first,” said David A. Drabkin, a former procurement official at the Defense Department.
A Defense Department procurement official is formally overseeing the cloud contract, known as the joint enterprise defense infrastructure, or JEDI. But Ms. Smith declined to identify the officials who would be involved with choosing the winner.
A White House official reiterated on Wednesday that the president was not involved.
The military has lagged behind the private sector in adopting cloud computing, but officials have made clear that they know the stakes. The Pentagon’s move to the cloud has been led by the chief information officer, Dana Deasy, a former global chief information officer at JPMorgan Chase.
“Battlefield advantage is driven by who has access to the best information that can then be analyzed to inform decision making at the point and time of need,” Mr. Deasy wrote last year.
Adopting technologies widely used in the private sector is key to the mission of the defense digital service, the Pentagon tech team Mr. Ubhi joined in 2016. It is unclear what Mr. Ubhi worked on during most of his time in government. But in his last two months, during fall 2017, he did market research for JEDI, according to the Pentagon.
In court documents, Oracle argues that Mr. Ubhi worked on JEDI when the Pentagon decided to take the approach of hiring a single cloud provider. Oracle cites internal documents in which Mr. Ubhi expressed support for a single cloud. When the Air Force awarded a different cloud project to multiple vendors, Mr. Ubhi wrote that the contract “makes me weep.”
Oracle says Mr. Ubhi clearly favored Amazon over other tech companies. In an online chat conversation on Slack about another cloud-computing provider, he sent a closed-eyes, tongue-out emoji.
Amazon has countered that the Pentagon identified 72 people substantially involved in developing the contract and its requirements, and that Mr. Ubhi worked on JEDI for only seven weeks, in the early stages.
At the end of October 2017, Mr. Ubhi recused himself from JEDI, saying Amazon and his restaurant start-up, Tablehero, “may soon engage in further partnership discussions.” Two weeks later, he resigned and then rejoined Amazon, where he still works on the commercial, not government, side of the business, the company said.
There is no evidence that Amazon bought Tablehero. Dheeraj Jain, an investor in Tablehero, said Mr. Ubhi has not responded to emails. “We have written off this investment, unfortunately,” he added. “And we are not happy about it.”
The Pentagon released the JEDI request for proposals nine months after Mr. Ubhi recused himself. It said a single cloud would let it move faster and with more security, a decision the Government Accountability Office later affirmed.
Because Amazon appeared to have a leg up, the contract immediately became a point of contention among tech contractors. Both Oracle and IBM filed protests with the Government Accountability Office, which adjudicates federal contract challenges. The office denied Oracle’s protest and later rejected IBM’s on procedural grounds. Oracle, whose cloud market share is small enough to be grouped in the “other” category in several leading research reports, took its fight to the United States Court of Federal Claims.
The delays from the Oracle lawsuit could help Microsoft. In the months since the request for proposals went out, the company, which has supplied the Pentagon for decades, has improved its capabilities to the point that some experts believe it is an increasingly credible competitor to Amazon.
But even if Mr. Ubhi is found to have tainted the contract, it is not clear that it would change the Pentagon’s plan to use a single cloud provider. The Government Accountability Office in November found that the Pentagon’s justifications “reasonably support” the decision. The office said it would be “improper” to go against what the Pentagon determined was best for the country, even if Mr. Ubhi had shaped the contract.
When he was working on the project, Mr. Ubhi said that bolstering national security was the point.
In October 2017, he wrote in a blog post that he believed his work on JEDI would “be a unique asset to help our men and women in uniform make more data-driven decisions, and to allow our leadership to be more effective.”
Little did he know, it seems, that his work on it could put the project on pause, or, if Oracle has its way, in jeopardy.
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