Emil Michael made his name in Silicon Valley a decade ago as an aggressive dealmaker for a startup — Uber Technologies Inc. — as it wrangled with governments in pursuit of market domination. Now, Michael has switched sides in a battle involving a different startup — this time taking a leading role in the Pentagon’s dispute with artificial intelligence pioneer Anthropic PBC.

As U.S. Under Secretary of Defense for Research and Engineering, Michael has been negotiating with Anthropic and its chief executive officer, Dario Amodei, over how the defense department can use its AI models. The discussions, centered on Anthropic’s aim to keep its technology from being used for mass surveillance of Americans and to power fully autonomous weapons, are at an impasse. The Pentagon formally notified Anthropic this week that it had determined the company to be a supply chain risk — a designation typically used only for foreign adversaries.

The episode has allowed Michael to reprise the some of the hardball tactics that defined his four-year tenure as chief business officer at Uber. The standoff has pitted the Defense Department against Anthropic, a leader in the industry, as well as a broad and vocal contingent of technologists worried over the use of AI in weapons.

Even has he spars with Anthropic, Michael is simultaneously trying to build positive relationships with tech companies, reaching out to potential partners to accelerate the military’s adoption of AI. Since he took the position in May, Michael has met with hundreds of tech companies, according to a department official. Part of the goal is to get the best AI technology into the hands of the government, work closely with a handful of leading players, and expand the universe of contractors the Defense Department typically deals with, the official said.

Michael has also kept up his direct relationships with investors — including some that back Anthropic, whom he has talked with in recent days, according to a person familiar with the matter who asked not to be identified discussing private conversations. During their chats, he has shared his perspective on the negotiations from the government’s side, they added.

Michael has been publicly critical of Anthropic, calling Amodei a “liar” with “a God-complex” in an X post last week. At Andreessen Horowitz’s American Dynamism Summit on Tuesday, Michael said that issues with an unnamed model vendor went “well beyond what you’ve been hearing in the press in the last couple of weeks.” He also said that the company had pushed for “dozens of restrictions. And yet these AI models were baked into some of the most sensitive and important places in the U.S. military.”

His fiery personality in government is in keeping with his reputation at Uber, where he served as former CEO Travis Kalanick’s right-hand man and was a fixture of its early successes. During his four years at the company, he helped transform Uber from a scrappy startup on tenuous regulatory footing into a household name and mainstay of global transportation. He also assisted with raising more than $10 billion. He oversaw Uber’s expansion into international markets such as China, and eventually Uber’s sale of its Chinese operations to rival Didi Chuxing.

Michael’s streak of victories at the company were punctuated by controversies. He was ultimately ousted in 2017 following an investigation into the ride-sharing company’s workplace culture helmed by former U.S. Attorney General Eric Holder. Holder’s report recommended Michael’s removal from the company among other leadership changes, Bloomberg reported at the time. Kalanick left soon after.

Michael had previously been involved in other high-profile scandals at Uber, including reports that he and other executives visited an escort-karaoke bar in 2017. He also suggested in 2014 that Uber could pay to dig up dirt on journalists critical of the company. He denies that he went after a reporter and in a statement at the time said he regretted the incident.

Still, some Michael allies are glad to see a seasoned business operator in government. “You want someone in the Pentagon who really understands technology and knows how to navigate the technology world,” said Joe Lonsdale, a conservative investor and a co-founder of Palantir Technologies Inc. And someone “who’s young enough that they’re still working 100 hours a week, super intensely.”

A former college Republican at Harvard University, Michael has prior government experience, too. Before joining Uber, Michael was a White House fellow under President Barack Obama and served as a special assistant to former Defense Secretary Robert Gates. During his tenure at Uber, he joined the Defense Business Board to lend his tech expertise to policy recommendations.

In the years following his departure from Uber, and before his Defense Department appointment, Michael was the CEO of a special purpose acquisition company called DPCM Capital.

His political donations, while limited, have crossed party lines. Most recently, he gave $1 million in 2024 to MAGA Inc., President Donald Trump’s super political action committee, Federal Election Commission records show. Earlier, Michael contributed $2,700 to Hillary Clinton’s 2016 presidential campaign.

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(With assistance from Bill Allison.)

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