President-elect Donald Trump's views on a range of issues, from immigration to climate change, alienated many left-leaning tech employees in Silicon Valley, but none more so than those working at Alphabet.
During the presidential campaign, 33 employees at the tech giant donated $20,000 to Trump, according to the Center for Responsive Politics. That was a tiny fraction of the 1,400 employees who donated to Hillary Clinton's campaign, for a total of $1.6 million.
And it wasn't just political donations.
The revolving door between the Obama administration and the company swung hard and frequently during the past eight years: 22 former White House officials left the administration to work for Alphabet, according to research from the Campaign for Accountability.
Alphabet's support for Clinton was evident in its C-suite as well.
WikiLeaks revealed that Executive Chairman Eric Schmidt emailed John Podesta — Clinton's campaign manager — volunteering to fund, advise and recruit talent for her White House run. CFO Ruth Porat donated $2,700 to Clinton, the maximum amount of money an individual can contribute to a federal campaign.
Like many tech companies, Alphabet has a range of potential political issues that it must consider, from immigration to privacy, taxes to encryption. There are also regulatory concerns.
In Europe, it is under fierce antitrust scrutiny. To date, the U.S. has been safer ground though CNBC reported last summer that officials from the Federal Trade Commission had deepened their analysis of the company's practices at home.
Regulators can have a real impact on Google, from forcing changes in its business model to blocking acquisitions. It remains an open question how the Trump administration will approach these sensitive issues.
For his part, Trump took tough, unverified shots at the iconic company on the campaign trail. For example, he accused Google of manipulating search results to favor his Democratic rival.
Despite this rocky history, both sides are now trying to find common ground as the inauguration approaches. Alphabet CEO Larry Page recently joined other tech leaders at a meeting with the incoming president. Meanwhile, Schmidt has been very visible at Trump Tower, visiting at least twice.
Stuart Roy, a veteran political strategist who used to represent the company in Washington, said that kind of outreach makes sense.
"It is clear that Trump values personal relationships much more than holding a vindictive grudge," says Roy, who is now president of the communications firm Strategic Action Public Affairs. "Google is clearly not starting from a strong position, but I do think there is a way they can build that relationship and build that trust."
While its relationship with the new administration is uncertain, Alphabet does have plenty of conservative friends on Capitol Hill.
Its top lobbyist is Susan Molinari, the former Republican congresswoman from New York. Last year, the company's political action committee donated $1.5 million to federal candidates, with 56 percent directed to Republicans.
Alphabet declined comment for this story.