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…
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