By Heather Somerville, Keach Hagey and Amrith Ramkumar
Emil Michael, the former Silicon Valley executive who has been the Pentagon's point person in its dispute with artificial-intelligence company Anthropic, prides himself on negotiating deals that leave even the losers feeling good.
But after what may be Michael's most public and consequential negotiation yet, no one is feeling very happy. Not Anthropic, which is suing the Defense Department for designating it a supply-chain risk, threatening its relationships with other customers. Not the Pentagon, which must now replace Anthropic's AI services throughout its systems even as it uses them to fight a war. Not even Anthropic's competitors, which have raised concerns about how the precedent could allow for government overreach and stunt the technology's development.
It's a rare miss for Michael. His conclusion: Anthropic, a company with an idealistic mission and a prickly relationship with the Trump administration, was never seriously interested in getting to yes.
"Even if you're a master dealmaker, at some point you realize the other side doesn't want to make a deal," Michael said Thursday in an interview with The Wall Street Journal.
As the department's under secretary for research and engineering reporting to Defense Secretary Pete Hegseth, Michael has been the public face of the Pentagon in a saga that has consumed attention spans in Washington and Silicon Valley. In posts on X, sometimes in all-caps, Michael has blasted Anthropic Chief Executive Dario Amodei, accusing him of lying and having a God complex. Amodei has called some of Michael's public statements lies and said he has mischaracterized the company's position, which is that it only sought assurances about guardrails for its technology.
But Michael insists that his behind-the-scenes discussions with Amodei were always polite and cordial. "He and I never yelled at each other, never screamed," Michael said.
Of his "edgy" posts on X, he said, "It was in response to their public denigration of this administration, our work and our mission. I was matching fire with fire," Michael said.
A little edginess is nothing new for Michael. In his time at Uber, where he spent four years as chief business officer and the closest confidant to then-Chief Executive Travis Kalanick, the company was in almost continuous conflict with local governments, regulators and labor organizations. Michael was personally involved in some of the controversial episodes that led to Kalanick's ouster, and his own.
Friends, associates, former colleagues and bosses describe Michael as a sharp-elbowed negotiator and a tactician who can turn a mess into a lucrative payday. They describe his negotiating style as patient, respectful and empathetic, even as he presses for maximum advantage.
"He is one of the best deal guys in the world. And he wants to play on the biggest field," said Joe Fernanzez, who founded the startup Klout in 2008 and spent eight months recruiting Michael to work for him as chief operating officer.
The Pentagon's decision to punish a tech company for refusing to comply with contract demands underscores the Trump administration's eagerness to integrate an evolving and powerful technology into the world's most powerful military, on its own terms.
Those who know Michael -- who is also a Stanford-trained lawyer -- chalk up his public bellicosity toward Anthropic to a fierce professional loyalty.
"Emil's job when he worked for Travis was to zealously represent Travis. And his job when he works for the Department of Defense is to zealously represent the Department of Defense," said Joe Sullivan, the former chief security officer for Uber.
In its lawsuit, Anthropic has warned that the administration's moves could cost it billions of dollars in revenue this year and hurt its future fundraising. Even as the company has accused the Defense Department of pressuring private-sector customers to turn their backs on Anthropic -- a claim Michael called absolutely untrue -- it has continued to insist it is eager to play a role in national defense.
Michael said the window for that has closed.
"There is no chance. There's no partnership that can be had."
Uber's A-team
Michael, 53 years old, was born in Cairo and grew up in New Rochelle, N.Y., where he attended public school. He went on to study government at Harvard University, where he got involved in Republican politics and joined a fraternity.
Michael left a job at Goldman Sachs for Silicon Valley during the dot-com boom and was an early employee at Tellme Networks, which made phone-based voice-recognition software. The company survived the bust and was sold to Microsoft for $800 million in 2007. Michael's job included convincing big, bureaucratic companies such as FedEx and AT&T to partner with a startup, said David Weiden, a founding partner at Khosla Ventures who attended Harvard with Michael and remains a friend.
He joined the Obama administration as a White House fellow and assistant to Defense Secretary Robert Gates. He has been a registered Republican since adulthood, but his financial contributions have split party lines, public records show. His largest was a $1 million donation in 2024 to MAGA, President Trump's super PAC.
He returned to Silicon Valley and eventually joined the so-called A-team at Uber, the inner circle that led the company to become one of the fastest-growing and most richly funded startups at the time. There, he leveraged his Goldman connections. He courted investors at San Francisco parties, bringing in large Middle East funds and eventually raising $20 billion. His preferred fundraising style was "less based on relationships, much more based on math and giving everyone a chance to participate," versus the clubby tactic of playing investors against each other, Michael said.
He secured $3.5 billion from the Saudi sovereign wealth fund to give Uber the leverage to strike a deal with its largest competitor in China, Didi Chuxing. Michael told Didi executives that Uber would spend the entire sum to compete with Didi in China if they didn't agree to buy Uber's operation there, which was burning $100 million a month. Michael completed the sale, which he called the most satisfying deal of his career, in two months. Uber took home around $7 billion.
In 2014, Michael and other Uber executives visited an escort karaoke bar during a work trip to South Korea, prompting an employee to file a complaint about the incident. Michael in 2014 publicly apologized after he suggested digging up dirt on the personal lives of journalists critical of Uber. One of his direct reports obtained and shared the private medical records of an Uber passenger who was raped in India. The incident prompted an investigation into alleged bribery by Uber executives and a lawsuit from the victim, although neither led to civil or criminal penalties.
In 2017, independent investigators determined that Uber tolerated a culture of sexual harassment and bullying, setting the stage for Kalanick's ouster. Around the same time, Michael left after the board pushed for his removal.
"Emil is one of the most inspiring and effective leaders I know. Our country is stronger, safer, and better because of his service," Kalanick told the Journal.
Deal collapses
After Uber, Michael led a lower-profile life, marrying and having two children. He founded a blank-check company with venture capitalist Shervin Pishevar, an Uber investor who was forced out of his own venture firm amid sexual harassment claims. Pishevar didn't respond to a request for comment.
Michael's name was in the mix for Transportation Secretary before Trump nominated him for the Defense Department role in late 2024, people familiar with the matter said. In a reorganization that began last year, six key organizations, including the military's AI office, were all put under Michael's purview.
"Coming to the department from the private sector, he is helping spur a new era of innovation," said chief Pentagon spokesman Sean Parnell.
Michael said his top priority is to accelerate the Defense Department's adoption of AI. "Moving fast to do that is very important when you have a four-year term."
After assuming his role, Michael reviewed the Pentagon's contract with Anthropic and found it relied on the AI company giving the department exceptions for using its tools in certain military scenarios, a clunky process. He began negotiating a new deal.
The Pentagon gave Amodei a Feb. 27 deadline for agreeing to new terms. After both sides went back and forth with proposals, Amodei on Feb. 26 said publicly the company was declining the Defense Department's latest offer and couldn't accede to its requests. The pre-emptive, public move by Amodei escalated the spat to Hegseth, after which there was a near-zero chance of reconciliation, an administration official said.
"It got out of my hands. I report to the secretary of war, who reports to the president," Michael said.
Michael said he spent the following weekend, after the deadline passed, trying to save the deal, without success. But ever the dealmaker, he was working other options. As Anthropic was bowing out, the department signed deals with two of its biggest rivals, OpenAI and xAI.
Write to Heather Somerville at heather.somerville@wsj.com, Keach Hagey at Keach.Hagey@wsj.com and Amrith Ramkumar at amrith.ramkumar@wsj.com
(END) Dow Jones Newswires
March 12, 2026 23:23 ET (03:23 GMT)
Copyright (c) 2026 Dow Jones & Company, Inc.
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