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Trump had made inflammatory positions on race and immigration central to his presidential bid. His campaign’s use of social media threw gas on the flames. On Facebook, the video of the anti-Muslim speech quickly generated more than 100,000 “likes” and was shared 14,000 times.

The video put the platform in a bind. It was unprepared for a candidate like Trump, who was generating a massive following but also dividing many of its users and employees. For guidance on this, Zuckerberg and Sandberg turned to their vice president of global public policy, who was in India trying to salvage Zuckerberg’s free internet service program.

Kaplan dialed into a videoconference with Sandberg, Head of Policy and Communications Elliot Schrage, Head of Global Policy Management Monika Bickert, and a few other policy and communications officials. Kaplan was thirteen and a half hours ahead of his colleagues at headquarters and had been traveling for days. He quietly watched the video and listened to the group’s concerns. Zuckerberg, he was told, had made clear that he was concerned by Trump’s post and thought there might be an argument for removing it from Facebook.

When Kaplan finally weighed in, he advised the executives against acting hastily. The decision on Trump’s anti-Muslim rhetoric was complicated by politics. All those years of financial and public support for Democrats had dimmed Facebook’s image among Republicans, who were growing distrustful of the platform’s political neutrality. Kaplan was not part of Trump’s world, but he saw Trump’s campaign as a real threat. Trump’s large following on Facebook and Twitter exposed a gaping divide within the Republican Party.

Removing the post of a presidential candidate was a monumental decision and would be seen as censorship by Trump and his supporters, Kaplan added. It would be interpreted as another sign of liberal favoritism toward Trump’s chief rival, Hillary Clinton. “Don’t poke the bear,” he warned.4

Sandberg and Schrage weren’t as vocal on what to do with Trump’s account. They trusted Kaplan’s political instincts; they had no connections to Trump’s circle and no experience with his brand of shock politics. But some officials on the conference line that day were aghast. Kaplan seemed to be putting politics above principle. He was so obsessed with steadying the ship that he could not see that Trump’s comments were roiling the sea, as one person on the call described it.

Several senior executives spoke up to agree with Kaplan. They expressed concern about the headlines and the backlash they would face from shutting down comments made by a presidential candidate. Trump and his followers already viewed leaders like Sandberg and Zuckerberg as part of the liberal elite, the rich and powerful gatekeepers of information that could censor conservative voices with their secret algorithms. Facebook had to appear unbiased. This was essential to protecting its business.

The conversation turned to explaining the decision. The post could be seen as violating Facebook’s community standards. Users had flagged the Trump campaign account for hate speech in the past, and multiple strikes were grounds for removing the account entirely. Schrage, Bickert, and Kaplan, all Harvard Law grads, labored to conjure legal arguments that would justify the decision to allow the post. They were splitting hairs on what constituted hate speech, right down to Trump’s use of grammar.

“At one point, they joked that Facebook would need to come up with a version of how a Supreme Court Justice once defined pornography, ‘I know it when I see it,’” recalled an employee involved in the conversation. “Was there a line they could draw in the sand for something Trump might say to get himself banned? It didn’t seem wise to draw that line.”

Facebook technically barred hate speech, but the company’s definition of what constituted it was ever evolving. What it took action on differed within nations, in compliance with local laws. There were universal definitions for banned content on child pornography and on violent content. But hate speech was specific not just to countries but to cultures.

As the executives debated, they came to realize that they wouldn’t have to defend Trump’s language if they came up with a workaround. The group agreed that political speech could be protected under a “newsworthiness” standard. The idea was that political speech deserved extra protection because the public deserved to form their own opinions on candidates based on those candidates’ unedited views. The Facebook executives were creating the basis for a new speech policy as a knee-jerk reaction to Donald Trump. “It was bullshit,” one employee recalled. “They were making it up on the fly.”

This was a critical moment for Joel Kaplan in terms of proving his value. Though unpopular to some on the call, he was providing crucial advice on a growing threat coming from Washington.

When Sandberg arrived at Facebook in 2008, the company had been neglecting conservatives. It was a critical oversight: where regulation over data collection was concerned, Republicans were Facebook’s allies. When the House of Representatives flipped to a Republican majority in 2010, Sandberg hired Kaplan to balance the heavily Democratic ranks of the lobbying office and to change the perception in Washington that the company favored Democrats.

Kaplan came with sterling conservative credentials. A former deputy chief of staff to President George W. Bush, he was also a former U.S. Marine artillery officer and Harvard Law School graduate who had clerked for Supreme Court justice Antonin Scalia. He was the antithesis of the typical Silicon Valley liberal techie and, at forty-five, a couple of decades older than much of the staff at MPK. (He and Sandberg had met in 1987, during their freshman year at Harvard. They dated briefly and remained friends after their relationship ended.)

Kaplan was a workaholic who, like Sandberg, prized organization. At the White House, he had kept a trifold whiteboard in his office with lists of all the hot-button issues facing the administration: the auto bailout, immigration reform, and the financial crisis. His job was to manage complex policy issues and prevent problems from reaching the Oval Office. He occupied a similar role at Facebook. His mandate was to protect the business model from government interference, and to that end, he was an excellent employee.

In 2014, Sandberg had promoted Kaplan to lead global policy in addition to Washington lobbying. For the past two years, Facebook had been preparing for a possible Republican administration after Obama. But Trump threw them off course. He was not of the Republican establishment. Kaplan’s political capital seemed worthless when it came to the former reality TV star.

And while Trump was creating new headaches for Facebook, he was also a power user and important advertiser. From the start of Trump’s presidential campaign, his son-in-law, Jared Kushner, and digital manager, Brad Parscale, put the majority of their media funds into the social network.5 They focused on Facebook because of its cheap and easy targeting features for amplifying campaign ads. Parscale used Facebook’s microtargeting tools to reach voters by matching the campaign’s own email lists with Facebook’s user lists. He worked with Facebook employees who were embedded in Trump’s New York City campaign headquarters to riff on Hillary Clinton’s daily speeches and to target negative ads to specific audiences.6 They bought thousands of postcard-like ads and video messages. They were easily reaching bigger audiences than on television, and Facebook was an eager partner. Trump became an inescapable presence on the platform.7