Expedia CEO Dara Khosrowshahi has reportedly been offered the top slot at Uber.
With Khosrowshahi in that role, Uber's tense relationship with the White House might continue. Khosrowshahi has not hidden his disapproval of some of the policies suggested by President Donald Trump.
In particular, Khosrowshahi opposed a travel ban aimed at several predominantly Muslim countries the administration said were associated with high rates of terrorism. Expedia was one of about 100 technology companies that challenged the ban in court.
"I emigrated here when I was 9 years old; my family had to flee Iran," Khosrowshahi told CNBC's Jim Cramer on "Mad Money" earlier this year.
"And we were very, very lucky to come to America and have the opportunities presented to us, and that's one of the things that makes America great. The power of immigration, the American dream — if you think about the power of the American dream — it is the best brand out there. It's stronger than Apple, and Microsoft and Google combined, times 10x."
He continued, "The American dream is you come here, you believe in democracy, you believe in the Constitution, you work hard, you can make it. That's what makes this country great, and I think the president should be for that, not against it."
Trump's opponent, Democrat Hillary Clinton, received by far the most donations from Expedia employees, at $30,429, including a donation from Khosrowshahi himself, according to OpenSecrets. Chelsea Clinton and outspoken Trump critic Barry Diller are both on Expedia's board.
Within Uber, that might not be so controversial: Employees there contributed $54,842 to Clinton's campaign, while Uber donated $190,000 to the host committee of the Democratic National Convention in Philadelphia.
But running Uber is far from an apolitical affair — the company itself was founded during the inauguration of Barack Obama. And former CEO Travis Kalanick, who is still on the board and has a large voting stake in Uber, left the company in a tough spot with both sides of the political spectrum.
The politics of running Uber
Earlier this year, the company faced a #DeleteUber social media campaign, after Uber lowered prices for rides to John F. Kennedy airport, seemingly defying the New York Taxi Workers Alliance protest of a proposed immigration crackdown.
After angering the political left, Kalanick tried to reroute the narrative, releasing a statement that he would stand up for "what's right" and raise the impact of the travel ban on "innocent people" with President Donald Trump at a meeting. Even that wasn't enough: Kalanick said his meeting with Trump was "misinterpreted" as an endorsement, and Kalanick left the president's business advisory council.
The prickly political situation with Uber is unlikely to get any easier. The company, which is already facing 20 years of FTC audits, is racing toward several skirmishes with the feds.
Uber's treatment of drivers as contractors — rather than full-time employees — has raised questions among politicians like Sen. Elizabeth Warren, D-Mass., when it comes to issues such as overtime and background checks. Then there's a federal investigation into the company's use of software to evade authorities, known as "greyballing." And don't forget that a lawsuit between Uber and Alphabet was also referred to a federal prosecutor.
Perhaps unsurprisingly, Uber has also stepped up its lobbying aggressively over the past two years, spending $800,000 this year alone, according to OpenSecrets, as the government decides regulations around such products as self-driving cars.