In retrospect, Obama wasn’t the first high-tech president just because he had a personal relationship with technology. He was also the president who oversaw Silicon Valley’s reincarnation, from industrial accessory of the PC and E-commerce era to information sovereign in the age of iPhone and Facebook. The Obama administration mostly supported the tech sector, implicitly or explicitly, and for worse as much as better.

Now that Trump is heading to the White House, things are likely to change. And Silicon Valley is worried. In July, a hundred tech-industry business leaders condemned Trump publicly, largely on social justice grounds. After his election, fear of a Trump presidency sent the tech industry into a tailspin. A prominent investor called for California to secede from the union. But once the dust clears, Trump might prove eminently compatible with Silicon Valley’s ongoing project. And if that’s the case, the technology industry’s mask of affable, harmless progressivism is about to be pulled off forever.

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In May 1998, the U.S. Department of Justice opened an anti-trust trial against Microsoft. It had been watching the company since the late 1980s, and with increasing scrutiny in the early 1990s. Microsoft’s DOS and Windows operating systems had helped the company reach a near-monopoly in the PC marketplace. In a 1994 settlement with the DOJ, Microsoft agreed not to bundle other Microsoft products with Windows. The 1998 trial centered on Internet Explorer, which Microsoft had started bundling with the OS. At issue was whether the web browser was a product or merely a feature—the latter was allowed under the terms of the 1994 settlement.

In 2000, the court determined that Microsoft had violated the Sherman Antitrust Act. It called for the breakup of the company. On appeal, the DOJ agreed to far less severe remedy, amounting to concessions in the way the company bundled software and provided access to APIs. Disdain for Microsoft among the judiciary and the states who had joined the lawsuit was evident throughout the trial and appeal. The company was seen as a bully in the market and a brat in the courtroom.

At the time, some criticized the DOJ, but mostly on the details. Few thought that antitrust litigation was an inappropriate intervention in the information technology industry. Indeed, it was a boon to the industry. Bill Clinton was perfectly happy to take credit for the technology boom that helped rescue the economy from the recession that preceded his presidency. In the new economy brought about by the web, incumbents like Microsoft represented resistance rather than opportunity. The brush had to be cleared.

It wasn’t the only way the Clinton administration helped the tech industry. Other Clinton policies of the mid-1990s were profoundly libertarian—among them, the transformation of the internet into a duty-free zone. In the ’90s, Silicon Valley was largely concerned with spreading the infrastructure of the internet via routers, switches, servers, and software; or in transforming traditional bricks-and-mortar businesses into online ones. E-commerce ruled the day, and an extended tax holiday offered online consumers a massive incentive to move their purchases online. This, along with other efforts to narrow the digital divide by broadening access to computers and the internet, made Clinton a strong advocate of Silicon Valley. At this time, the government’s primary concerns about the internet amounted to protecting children from predators and undesirable content.