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Facebook’s allowance of the post triggered a “virtual walkout” by about 400 staff, according to the New York Times. In the company’s private chat channels, some called for Kaplan’s resignation.

In mid-June, leading civil rights groups launched an advertising boycott against the company, called Stop Hate for Profit. By July it had gathered about 1,000 corporate participants (including Verizon, which owns Yahoo Finance).

For more than a year, one of the boycott leaders, Color of Change, had already been specifically calling for Kaplan’s ouster in an online petition. “He is the one … who is constantly preaching false messages of [bias against conservatives],” says Arisha Hatch, the group’s vice president and chief of campaigns, “the one pushing for a neutral approach when we feel like there’s no neutral approach to hate speech, no neutral approach to racism.”

The case against Kaplan was encapsulated in a tweet by Kevin Roose, a New York Times technology columnist and podcast host. Linking to a Washington Post article, which outlined a bill of particulars against the executive, Roose wrote: “Joel Kaplan was hired to lobby Republicans on behalf of Facebook, but this story makes it pretty clear that his actual success has been lobbying Facebook on behalf of Republicans.”

Still, Kaplan has defenders, and they raise doubts about the prosecution narrative. To begin with, the notion that Kaplan has been pursuing some personal or political agenda apart from his employer’s is unimaginable to some who know Kaplan well.

“I can see people disagreeing with him, but I cannot see people calling into question his integrity,” says Josh Bolten, the former White House Chief of Staff who was Kaplan’s boss for eight years during the Bush Administration.

Second, Kaplan’s supporters argue that he can’t be carrying water for Trump—because he’s not a Trump guy. Shortly after the 2016 election (as has been previously reported), while consoling distraught colleagues at an all-hands video-conference, Kaplan assured them that he had not voted for Trump. In interviews for this article, three longtime friends say they’re confident he’s not voting for Trump this time. (President Bush himself—with whom Kaplan is still friendly—has said he will not vote for Trump, and scores of former Bushies have formed a super PAC supporting former Vice President Joe Biden)

Third, Kaplan’s defenders suggest that his niche on Facebook’s organizational chart draws into question the notion that he could be as responsible for controversial Facebook policies as his critics believe him to be. Kaplan is three rungs down from Zuckerberg, to whom many of the landmark content controversies over the years have been “elevated,” in the company’s lingo. Just below Zuckerberg (for content issues) is chief operating officer Sheryl Sandberg, a major Democratic donor and former chief of staff to President Bill Clinton’s Treasury Secretary. Beneath her have been Kaplan’s direct bosses over the relevant years—the successive heads of global communications and public policy. Until October 2018, Kaplan’s boss was Democrat and long-time human rights advocate Elliot Schrage; since then, the post has been held by U.K. Liberal Democrat and former deputy prime minister Nicholas Clegg.

It’s not credible, Kaplan’s apologists protest, that all these powerful liberals have repeatedly stood mute while the Republican single-handedly persuaded Zuckerberg to steer the company to serve conservative political interests. They suggest that the criticisms of Kaplan are political scapegoating. (Zuckerberg has been tight-lipped about his own politics, but he is a strong advocate of open immigration, criminal justice reform, and LGBT rights.)

The case against Kaplan “is a false narrative that politicizes principled decisions pursued in good faith,” asserts Schrage, who was Kaplan’s boss from 2011 to 2018.

In interviews with Yahoo Finance, Schrage insists that he was actively involved in many of the decisions Kaplan is now being faulted for, and that he and Kaplan agreed the lion’s share of the time. The anti-Kaplan narrative should founder, he continues, once readers understand that Schrage—a Democrat and Kaplan’s boss—was fervently advancing the same positions Kaplan was.

‘Political biases, but not a political agenda’

In this profile, we attempt to flesh out Kaplan more fully than ever before. Who is he, and how has he spent his career? How plausible are the defenses raised on his behalf? (Kaplan declined to be interviewed for this story.)

Some readers will doubtless find only more reasons for anger. Others may see Kaplan in a more complicated light.

As we’ll see, Kaplan grew up in comfortable circumstances and climbed quickly into the most privileged rungs of society. He did so through merit, ambition, diligence, and public service. He compiled a remarkable, largely unsung, career.

Nine people who have known Kaplan at different stages of his life describe him in terms that cut against the grain of the prevailing narrative. They claim that he is distinguished by “piercing intellect,” “discipline,” fairness, and “principle.” A frequently recurring phrase is “honest broker.”

“He has political biases, but not a political agenda,” says one former Facebook colleague.

What to make, then, of all the accusations against him? There’s a steady drumbeat of these accounts—including two articles earlier this month—and they are very consistent with one another. Together, they form a powerful indictment. Kaplan is repeatedly described as hypersensitive to conservatives’ accusations of platform bias and excessively worried about conservative backlash.

A countervailing question is this: To what extent do these accounts reflect that he’s a conservative surrounded by liberals in an exceedingly partisan moment in our history? Or, for that matter, that he’s doing his job? Part of which is to ensure that this company, whose 52,500 employees are overwhelmingly Democrats, is perceived as fair by the roughly half of American users who are not. (In the 2016 election cycle, 93 percent of Facebook employee’s political donations went to Democrats, according to GovPredict.)

Distasteful though it may be for some liberals, being seen as fair to conservatives is a sensible goal for a public company, and especially one that serves as a communications platform.

“I never detected any hint that [Kaplan] was acting outside of what he and others in the company thought was Facebook’s best interest at the time,” says another former Facebook colleague. “In retrospect, I view him as being in an impossible, no-win situation.”

It’s certainly a challenging job. When 2.7 billion users are firing off 100 billion posts a day in more than 100 languages under scores of legal regimes, censoring speech in a principled way is a Sisyphean task.

And Kaplan’s challenge goes beyond even that. Another part of his job is to accommodate political speech from “both sides” at a time when “both-sides-ism” is a term of opprobrium. (Notwithstanding its laissez-faire record compared to Twitter in recent months, Facebook has taken down certain Trump campaign posts for rules violations. It removed one in March, judged to contain misleading information about the census; another in June, for using a Nazi symbol; and a third, this month, for providing misinformation about the coronavirus.)

“I just personally find it very ironic that at this large business there seems to be no space for any diversity of ideas as it comes to politics,” says a longtime friend of Kaplan’s from Bush circles, Dylan Glenn. “He’s the only conservative around the table, and he’s seen as an advocate as opposed to trying to raise the value of the business by having people be sensitive to all of the potential perspectives.”

Given the stakes of the coming election, it might be that some of Kaplan’s critics would be uncomfortable with any Republican in his position. And to placate Facebook’s most ardent critics, all of Facebook’s leadership would have to resign en masse.

These are thoughts to keep in mind when weighing, below, Kaplan’s record, the charges against him, and the arguments mounted in his defense.

‘A Mitt Romney conservative’

Joel David Kaplan, 51, was born May 9, 1969. He grew up in the suburb of Weston, Mass., about 20 miles west of Boston. His father worked as a labor-side labor lawyer, and his mother as a teacher and educational administrator. They were Democrats.

“I moved to Weston when I was 14,” says Nigel Jones. He met Kaplan at Weston’s public high school. At the time, some Black students were being bussed in to the school.

“But I was the only Black kid who actually lived in Weston,” Jones recounts. “[Kaplan] was the first person to reach out to me and welcome me into his circle of friends.” More than 20 years later, Jones served as Kaplan’s best man, and Kaplan as Jones’. They remain close. (Jones is now CEO of KoolSpan, a company that sells secure mobile communications solutions for enterprise clients.)

In 1987, the two young men continued on to Harvard College. Freshman year, Kaplan and Sheryl Sandberg were assigned to the same dorm, while Jones lived at the neighboring one.

“We were all good friends,” says Jones, demurring on whether, as reported, Kaplan briefly went out with Sandberg. “We were all generally in the same social circle—the more social people in the freshman class.” When Jones later joined a “finals club”—Harvard’s elitist version of the fraternity experience—Kaplan declined, because the clubs did not admit women at the time.

After graduation, in 1991, Kaplan and Jones both joined the Marines, eventually ending up at Camp Pendleton together. Kaplan became an artillery officer, leading a battery of 150 Marines. He oversaw six M198 Howitzer systems (a 16,000-pound cannon, basically), along with other weapons systems and logistics chains.

In the fall of 1995, Kaplan entered Harvard Law School. There he won the Sears Prize, awarded to the two first-years with the highest grade point averages. This made him one of the most highly sought-after law students in the country.

Upon graduating in 1998, he took a judicial clerkship that was logical in some respects, but jarring in others. Judge J. Michael Luttig, who sat on the U.S. Court of Appeals for the Fourth Circuit, was a logical choice in that he was a “feeder” judge. Nearly all his clerks went on to clerk for Supreme Court justices—the admission ticket to the profession’s most rarefied ranks.

In addition, Luttig was widely considered Supreme Court timber himself. He was a hard-right, Federalist Society-groomed wunderkind, whom President George H. W. Bush had appointed to the bench at age 37—then the nation’s youngest appellate judge. Later, in July 2005, reporters would stake out Luttig’s home when President George W. Bush was due to make his first selection. The nod went to John Roberts, Jr., instead.

What made the Luttig clerkship an unusual choice was that Kaplan was then still a registered Democrat. Though Kaplan was obviously in political transition, his close friends recall no conversion.

“I don’t think his views shifted so much as the parameters around the parties shifted,” says Jones. “Joel has been remarkably consistent in his values and beliefs over as long as I’ve known him. Which is, broadly speaking, a Mitt Romney conservative.”

In mid-July 1999, Kaplan moved on to clerk for Supreme Court Justice Antonin Scalia. About a year later, as he was finishing there, Josh Bolten heard about him. Then policy director for the Bush-Cheney campaign, Bolten called Kaplan and hired him over the phone. (Josh Bolten is no relation to John Bolton, Trump’s former National Security Advisor.)

The two had a lot in common. Bolten was a nonpracticing lawyer, Jewish, and someone who had acquired a reputation as an honest broker in contentious, political milieus. Bolten would keep Kaplan close for the next nine years. (Today, Bolten is CEO of the Business Roundtable.)

After the too-close-to-call November 2000 election, Kaplan was sent to Florida for what turned out to be his most controversial, pre-Facebook assignment. He’d been selected to be the Bush camp’s court-appointed observer as the Miami-Dade County canvassing board counted “hanging chads.”

That put Kaplan very close to the notorious, so-called Brooks Brothers Riot, in which about a dozen Bush operatives, pretending to be outraged locals, led a raucous protest that intimidated county officials into halting the recount. Some media accounts later identified Kaplan as a participant.

Kaplan has denied that. When asked about it at his Senate confirmation hearing (for the post of deputy director of the U.S. Office of Management and Budget in 2003), he testified carefully: “I was attempting to get into the room, where I was permitted and invited to be,” he said. “What I saw before I went into the room was a group of people protesting, and I didn’t see anything that suggested any violence …. So while I was there, I was not, to my recollection, a participant.”

When Bush took office, Bolten became deputy White House chief of staff for policy (reporting to Andrew Card). As his two assistants, Bolten chose Kaplan and Kristen Silverberg, who later became U.S. Ambassador to the European Union. The two shared a windowless, ten-by-ten-foot office in the West Wing. Then 31, Kaplan began attending meetings with the president about once a week. For unknown reasons, Bush nicknamed him “angular dude,” Bolten and Silverberg recall.

Silverberg remembers a helpful piece of advice Kaplan gave her then. When she’d be second-guessing herself over a past decision, he’d tell her: “Shot out.” It was an artillery expression, she explains. It meant that the shell had been fired, it was over-and-done-with, and it was time to move on.

On September 11, 2001, after the terrorist attacks, Kaplan and Silverberg were evacuated to a nearby commercial office building. There they huddled with speechwriters to sketch out the White House’s first post-attack public remarks.

“This was literally just hours after,” says Silverberg. “Joel said two things to the speechwriters. First, this isn’t going to be a war on Muslims. And second, we’re going to have to convey that every American has a contribution to make. He felt that people needed us to steer them in a way where they could help.”

“The speechwriters kind of brushed him off,” Silverberg recounts. “But those were the themes we went back to for the next ten months.” (Kaplan’s second point was the kernel of the idea that later became the USA Freedom Corps, Silverberg says.)

In the days that followed, Kaplan and Silverberg tackled a range of sui generis tasks: getting planes back in the air; getting the stock market back up and running; and helping New York City find adequate morgue capacity.

After the situation stabilized, Bolten, Card, and, eventually, President Bush came to see a need to form what became the Department of Homeland Security. To avoid turf wars, Card and Bolten delegated the task to just five White House officials who worked in secrecy. Its leaders were Kaplan and Rich Falkenrath, who later became deputy commissioner for counter-terrorism for the New York City Police Department. So confidential was their work that they sometimes reported to superiors in the White House bunker, Bolten recalls. Only when they were nearly done were even Cabinet secretaries informed, he adds.

What they came up with was the largest government reorganization since the creation of the Defense Department in 1947, with some 22 agencies and departments being consolidated.

As a former Supreme Court clerk, Kaplan often socialized with the other young attorneys working in the West Wing, Bolten recalls. Kaplan became particularly close with then-associate White House counsel Brett Kavanaugh, who was four years older. (He’d first met Kavanaugh through legal circles in the late 1990s, according to Facebook’s Stone.)

In 2003, when Bolten became director of the Office of Management and Budget, he took Kaplan with him as his deputy. In his new role, Kaplan often worked with Kavanaugh, who had, by then, become Bush’s staff secretary. (The staff secretary manages the paper flow to the President and his staff. Justice Kavanaugh declined comment for this article.)

Kaplan was now dating Laura Lyn Cox. Raised in the tiny hamlet of Rising Star, Tex., Cox was then transitioning from a legislative affairs post in the Treasury Department to a position on the senior management team of S.E.C. Chairman William Donaldson.

Kavanaugh, for his part, was dating Ashley Estes, of Abilene, Tex., an hour west of Rising Star. She was President Bush’s personal secretary—the woman who sat just outside the Oval Office, where Kavanaugh’s role as staff secretary so often took him. Cox and Estes soon became as tight as their boyfriends. (When Kavanaugh married Estes in 2004, Bolten remembers Kaplan joking at the rehearsal dinner: “Good things come to those who wait—outside the Oval Office.”)

In April 2006, Kaplan and Cox were married. At the rehearsal dinner, Bolten recalls, Kaplan thanked Cox’s non-Jewish parents for welcoming him into the family. He joked that the last time he had visited, he noticed they’d even changed the town’s name to Rising Star of David.

The newlyweds had to cut short their Hawaiian honeymoon. Bolten was returning to the West Wing as chief of staff—succeeding Card. Kaplan would be his deputy—the position Bolten held when the Administration started.

The war in Iraq was going poorly. Although Kaplan had not been involved in the decision to go to war—handled through the National Security Council—he participated in the decision-making that led to the “surge” in January 2007, says Bolten, which was the deployment of 20,000 additional soldiers to Iraq.

Kaplan was also the White House point person on a comprehensive immigration bill that failed to win passage—not unlike one the Obama Administration unsuccessfully tried to pass a few years later.

“I’m sad neither Ted Kennedy nor John McCain is alive today,” says Bolten—referring to two of the senators Kaplan worked with on the bill—"because they’d both give you an interview praising Joel.”

In 2008, the financial crisis hit.

“When the gravity of the situation became clear, I asked Joel to go over and embed himself with [Treasury Secretary Hank] Paulsen’s team,” Bolten says. “He was involved in a lot of the decision-making around TARP [The Troubled Asset Relief Program] and the rescue.”

On balance, Bolten places Kaplan at the “center center right” of the political spectrum. He believes in “pro-growth economic policy, fiscal responsibility, an assertive U.S. presence in the world,” and a “welcoming” immigration policy. In other words, Bolten concludes, “Joel is on the complete opposite side” of the key tenets currently associated with the right: “nativism, protectionism, and isolationism.”

As an employee, Bolten describes Kaplan this way: “He always had views, and wouldn’t be shy about giving them when appropriate. But he was scrupulously fair in articulating other people’s opinions and giving them the weight they deserved. In many cases, he would state a case that he didn’t agree with better than the proponent of that case. And thereby give the President a real opportunity to see what it was he really needed to decide.”

In January 2009, President Obama took office. After eight years in government, it was time for Kaplan to make some money. He and Laura had one small child already, and another on the horizon.

With a Democratic Administration taking over, his next step wasn’t obvious. Several Bushies invited Kaplan to join them at a venture called Energy Future Holdings Corp (EFHC). It was the product of the largest leveraged buyout in history. In 2007, three private equity groups—KKR, TPG Group, and Goldman Sachs Capital—had acquired TXU Corp. (the former Texas Utilities) for $45 billion.

EFHC never seemed like a good fit for Kaplan, several of his friends say. But it offered him a good salary and an equity stake, according to someone who then worked with one of private equity groups. And if the price of natural gas went up—the central bet at the core of the buyout—Kaplan would be rich.

He took the job. But almost immediately the fracking industry took off, and the price of natural gas plummeted. The job was grueling, too. Kaplan was commuting to Dallas, while Laura stayed in Washington, where she was now a partner at PriceWaterhouseCoopers, running its regulatory affairs team.

Controversy after controversy

In June 2011, he jumped to Facebook as head of U.S. public policy. He answered to global policy chief Marne Levine, the former chief of staff to President Obama’s National Economic Council. Hiring Kaplan was widely seen as an attempt by Facebook to improve its relationships with Republicans, who had just taken control of the House.

Kaplan’s boss, Levine, answered to Schrage. Schrage became a Kaplan fan. “[Kaplan]’s an extraordinarily disciplined thinker,” he says. “A consummate professional. Responsible. Ethical. Collegial. Supportive. Funny. Insightful. Unflappable. Entertaining. He’s the person you want beside you in a foxhole.”

Which is, metaphorically, where the two soon found themselves. When Levine was named Instagram’s chief operating officer in October 2014, Kaplan was promoted to her spot. So Kaplan was in the line of fire when Donald Trump announced his presidential candidacy in June 2015.

Trump’s incendiary and frequently false messaging would pose singular challenges for both digital platforms and the media. In the years that followed, coping with Trump would trigger soul-searching, firings, resignations, and protests in both industries.

At Facebook, an early test case was Trump’s December 2015 post linking to a speech in which he called for a “total and complete shutdown of Muslims entering the United States.”

Zuckerberg, a strong supporter of open immigration, was reportedly shocked by the message, and some members of the policy team wanted to remove it as hate speech. Kaplan was among the voices counseling Zuckerberg to leave it up. Kaplan “argued that Mr. Trump was an important public figure and that shutting down his account or removing the statement could be seen as obstructing free speech,” the New York Times later reported. Warning of “conservative backlash,” he also said, “Don’t poke the bear,” according to the Times.

“Joel and I were completely aligned in maintaining that it was inappropriate to silence a leading political candidate in a democratic society,” says Schrage.

Schrage is a Harvard Law School grad who once co-taught a Columbia University course with Nadine Strossen, who later became president of the ACLU. Schrage describes himself as a Brandeisian on free-expression issues. Supreme Court Justice Louis Brandeis famously wrote in 1927 that the proper remedy for false speech is “more speech, not enforced silence.” Schrage holds the perspective, he notes, that, in 1978, led the ACLU to defend the right of Nazis to march through Skokie, Ill., even though many Holocaust survivors were still living there at the time. (Facebook’s policies do not go that far. Facebook says it will remove explicit white nationalist speech. It won’t, however, intervene with respect to implicit messages—a central bone of contention for many civil rights advocates, including those who sharply criticized the company last month in an 89-page audit. Facebook also permits Holocaust denial.)

From a Brandeisian perspective, Schrage explains, the messages of a political candidate were not only newsworthy, but were also certain to provoke “counterspeech”—i.e., speech that holds the original speaker accountable. From that perspective, it made sense for Facebook to give political figures more leeway than ordinary users.

About ten months later another momentous case arose. Someone in Norway had posted the Pulitzer Prize winning photograph, The Terror of War, showing a naked, nine-year-old Vietnamese girl fleeing a napalm attack in 1972. Facebook had removed it, mechanically following its rules on community standards relating to nudity and child exploitation. After enduring worldwide derision, Facebook reversed its decision and then, a month later, Kaplan co-authored a post articulating the broader principle. “In the weeks ahead,” he wrote, “we’re going to begin allowing more items that people find newsworthy, significant, or important to the public interest — even if they might otherwise violate our standards.”

In effect, the Terror of War decision built upon the Muslim ban precedent. “Our burgeoning jurisprudence on expression needed to have flexibility,” Schrage says. “The position that I took was that we should not be in the business of constraining expression that would otherwise be legitimate in other media.”

In the aftermath of Trump’s electoral victory, Kaplan reportedly took still more controversial stances. The backdrop for one of them was this: In early January 2017, the U.S. Director of National Intelligence issued a politically explosive report revealing that, during the 2016 campaign, Russia had conducted covert influence campaigns across American social media platforms. President Vladimir Putin’s goal had been to “undermine public faith in the US democratic process,” the DNI wrote. “We further assess that Russia developed a clear preference for President-elect Trump.”

Independently, Facebook had been gradually realizing that various actors—including some with Russian IP addresses—had used fake accounts to disseminate political disinformation across its platform. A group at Facebook, including then-chief security officer, Alex Stamos, was working on a white paper about that activity.

When the paper came out, it did not contain the word “Russia.” Instead, it said that Facebook’s data did “not contradict” the DNI report, to which it linked in a footnote.

A New York Times story later suggested that Kaplan had pressed for omitting mention of Russia. “If Facebook implicated Russia further, Mr. Kaplan said, Republicans would accuse the company of siding with Democrats,” according to the newspaper.

The story also said that Kaplan had opposed pulling down fake accounts, fearing angry reaction from duped users. “His own mother-in-law, Mr. Kaplan said, had followed a Facebook page created by Russian trolls,” according to the Times’ sources.

Both Schrage and Facebook deny that Kaplan played any role in the decision not to mention Russia in the white paper. Facebook’s Stone also denies that Kaplan opposed taking down fake pages. If pages were going to be taken down, however, Kaplan first wanted a policy put in place explaining why they were, Stone maintains. (The company eventually announced a policy forbidding “coordinated inauthentic behavior.”) Once the white paper was complete, Kaplan did advise Facebook officials on how to brief members of Congress on it, Stone acknowledges.

The arguments about whether to mention Russia were between Stamos and Schrage (not Kaplan), according to Schrage. “My question was: Are the only actors in Russia that intervene formal government actors, or could there be other actors?” says Schrage. “And his answer was, ‘We don’t have eyes on the ground, but we don’t know why anyone else would be doing this.’ And my feeling was, we should signal it’s Russia, but not assert it’s Russia.” (Stamos did not return messages.)

In 2017 and 2018, Kaplan upset still more Facebook employees, this time on its product side, which was ordinarily outside his bailiwick. He voiced skepticism toward major projects being pursued by Facebook’s News Feed engineers. A task force called Common Ground was trying to make the site more civil and less polarizing by instituting certain algorithmic changes.

Again, the crux of the dispute hinged on whether the changes would be seen as biased against conservatives, according to two Wall Street Journal articles. Kaplan had argued that aspects of the project seemed “paternalistic”; that the term “Common Ground” was “patronizing”; and he “questioned if outsiders validated [the engineers’] definitions of ‘toxic’ and hateful,’ according to the Journal.

In a rare interview, Kaplan told the paper that he had approved of some of the changes. In opposing others, he maintained, “he was trying to ‘instill some discipline, rigor and responsibility into the process’ as he vetted the effectiveness and potential unintended consequences of changes to how the platform operated.”

Schrage says that he was involved in the Common Ground discussions, too. Some of the disputes revolved around transparency, he contends. Schrage wanted the company to be open with users about what was happening, while the engineers feared that too much transparency would invite gaming the system, he says.

In the end, some proposals were accepted, some weakened, some shelved. At least some of these issues were elevated all the way to Zuckerberg, as the Journal reported. The CEO “signaled he was losing interest in the effort to recalibrate the platform in the name of social good,” the paper reported, and not to bring these sorts of proposals to him again.

In the summer of 2018, still another controversy arose. “Kaplan pushed to partner with right-wing news site The Daily Caller’s fact-checking division after conservatives accused Facebook of working only with mainstream publishers,” the Wall Street Journal reported that December. Co-founded by Tucker Carlson, The Daily Caller’s journalistic standards had been called into question by some prominent journalists and it had published writings sympathetic to the Alt-Right, including those of an organizer of the white nationalist Unite the Right rally in Charlottesville. (The publication later removed that contributor’s work.)

Facebook’s Stone says that when Facebook started using independent fact-checkers in 2016, it decided to retain groups certified by a unit of the Poynter Institute. (This was meant to lend some objectivity to the process.) Daily Caller then set up a subsidiary, Check Your Facts, that met Poynter’s requirements, got certified, and applied to become a Facebook fact-checker. (Not all Poynter-certified fact-checkers are allowed to become Facebook fact-checkers.) Kaplan—and, again, Schrage—were among those who argued that Facebook should let it. The controversy reached Zuckerberg, and CYF was allowed to participate.

That summer, Trump nominated Brett Kavanaugh to the U.S. Supreme Court. The appointment would move the Court markedly to the right, threatening the demise of Roe v. Wade.

Shortly before the confirmation hearing, it emerged that Christine Blasey Ford, a psychology professor, was accusing Kavanaugh of having sexually assaulted her while he was drunk at a party in high school. Then a second woman came forward, Deborah Ramirez, who alleged that Kavanaugh had aggressively exposed himself to her at a drunken party in their freshman year at Yale College. (Kavanaugh categorically denied both accusations.)

The hearing became a historic, wrenching, he-said-she-said faceoff. To make matters worse, Senate Republicans—fearful of losing seats in the approaching midterms—were rushing the proceedings and truncating investigation of the allegations.

Finally, the nominee—protesting character assassination—lashed out at the inquiry itself as a “circus,” “a calculated and orchestrated political hit,” and “revenge on behalf of the Clintons.”

When Kavanaugh delivered this tirade, Facebook employees watching on TV or following on Twitter were shocked to see Kaplan seated prominently in the second row, conspicuously supporting the nominee. (In the iconic photos of Kavanaugh’s testimony, the grimacing blonde woman in the front row to Kavanaugh’s right, next to Kavanaugh’s wife, is Kaplan’s wife.)

Hundreds of workers lit up the company’s internal message boards with complaints, according to the Times. “Many employees also viewed it as a statement: Mr. Kaplan believed Mr. Kavanaugh’s side of the story rather than Dr. Blasey’s testimony.”

“Let’s assume for a minute that our VP of Policy understands how senate hearings work,” read one of the internal posts quoted by the Times. “His seat choice was intentional, knowing full well that journalists would identify every public figure appearing behind Kavanaugh. He knew that this would cause outrage internally, but he knew that he couldn’t get fired for it. This was a protest against our culture, and a slap in the face to his fellow employees.”

Even some Facebook colleagues who understood Kaplan’s desire to show loyalty to his friend felt he should have at least taken a less conspicuous seat, so as not to imply the company’s support for the nominee.

Kaplan apologized in a note to staff a few days later. In a separate message, to his policy group, he explained that Kavanaugh and his wife were Kaplan and his wife’s “closest friends in D.C.” and that “our kids have grown up together.”

Sandberg posted internally: “I’ve talked to Joel about why I think it was a mistake for him to attend given his role in the company.”

Not surprisingly, Kaplan’s friends interviewed for this story uniformly applaud what he did.

“I think that was actually a testament to his character and integrity that he was there for his friend in that trying time,” says Jones.

A few days after apologizing, Kaplan and his wife hosted a confirmation party for Kavanaugh at their home, leaving many employees feeling sucker-punched. Sandberg said that that was different, though, since it wasn’t a public appearance. “It’s his house,” she told Wired.

Kaplan’s handling of the Kavanaugh hearing greatly increased his public profile—and not in a good way. Although he had been ruffling liberal feathers internally at Facebook for years, many of those frictions did not start surfacing in the media until after the hearings.

If Kaplan doesn’t survive at Facebook, it will likely be because of that event.

Nick Clegg took over Schrage’s post in October 2018. (Schrage stayed at Facebook through December 2019, working on “other projects,” he says.) Some speculate that perhaps Kaplan’s influence on Zuckerberg has grown since Schrage left, since it would only be natural for the CEO to give more weight to Kaplan’s insights on American politics than to the Brit’s.

But there’s no evidence Facebook’s outlook toward free-expression has budged. In a September 2019 speech, for instance, Clegg announced that Facebook would not fact-check political ads. It was a bombshell decision that led at least 250 employees to sign a petition protesting it, according to the Washington Post.

But Clegg admitted that the policy had actually already been in effect for “over a year.” (Facebook has never fact-checked political ads, spokesperson Stone tells Yahoo Finance.)

In defending the policy, Clegg described it as the natural outgrowth of the company’s earlier “newsworthiness” exemption. He echoed the same Brandeisian “counterspeech” arguments that had been raised in the context of Trump’s Muslim-ban post in 2015. “In mature democracies with a free press,” Clegg said, “political speech is already the most scrutinized speech there is.”

That fall, Senator Elizabeth Warren (D-Mass.), running for president, singled out Kaplan as the poster boy for widespread government-industry, revolving-door practices that she wanted to outlaw. He had joined Facebook “just two years” after serving in the Bush Administration, she wrote in a policy statement, and the company was now spending “nearly 100 times [on lobbying] what it had spent before Kaplan joined” (eight years earlier). She proposed a four-year hiatus before senior government officials could join companies worth more than $150 billion.

“Meanwhile, Kaplan continues to flex his Washington rolodex,” Warren continued, “sitting directly behind Brett Kavanaugh in a show of support during his confirmation hearing, hosting a party for Kavanaugh after he was confirmed, and accompanying Mark Zuckerberg at a recent closed-door charm offensive with Republican lawmakers.” (Zuckerberg and Kaplan had also held closed-door meetings with Democratic lawmakers, according to both the article Warren linked to and Facebook’s Stone.)

This past April, the Tech Transparency Project issued a report revealing that far-right extremists, including white-supremacist linked “boogaloo” groups, were using private Facebook groups to plot militant uprisings. The project detected 125 such groups on the platform exchanging “detailed information and tactics about how to organize and execute a revolt against American authorities.” The groups were operating “without any apparent intervention by Facebook,” the project said.

The Transparency Project’s report prompted a sharp letter to Zuckerberg from three U.S. Senators. “We write to express our serious concerns about Facebook’s lack of action to prevent white supremacist groups from using the the platform as a recruitment and organizational tool,” wrote Senators Mark Warner (D-Va.), Mazie Hirono (D-Haw.), and Robert Menendez (D-N.J.). They demanded answers to 12 questions. Two of their questions singled out Joel Kaplan by name, asking about his role in squelching the Common Ground programs and the decision to let The Daily Caller’s subsidiary act as a fact-checker.

Five days after the senators wrote, Facebook announced the removal of a boogaloo network consisting of 220 Facebook accounts and 95 Instagram accounts, as well as the removal of 400 additional groups judged “dangerous” under its policies. It said the action was the product of operations that had been underway for months.

Two weeks later, a Facebook inhouse lawyer responded to the senators’ letter. She alluded to an op-ed by Nick Clegg denying that the company benefits from hate; stressed the challenges it faces in policing the platform, the billions of dollars it has invested in the effort, and the progress it’s made. She provided no information about Kaplan.

At 12:53 a.m. ET on May 29, Trump posted on Facebook his warning that if the “very weak Radical Left” mayor of Minneapolis did not “get his act together,” Trump would send the National Guard. He then added, “when the looting starts, the shooting starts.”

Zuckerberg was asleep at the time, he recounted three days later during a company-wide Q&A. (A tape was obtained by Vox’s Recode, and a transcript published.) While he slept, members of Facebook’s policy team in London and Washington prepared a memo, researching the history of the “looting-shooting” phrase and analyzing how the post fit into Facebook’s daunting matrix of community standards rules.

By the time Zuckerberg awoke at 7:30 a.m. PT, the memo was ready. The post could be read in three ways, it advised (according to Zuckerberg’s Q&A remarks). The first, and most reasonable reading, was that it was a warning about a potential “state use of force.” Facebook allows that.

The second best reading was that it was “a prediction of violence in the future”—not encouragement of violence. That, too, was allowed.

The third—but least likely—reading, was that it was an “incitement to violence,” which, under Facebook rules, would be taken down. (There is no “newsworthiness” exemption for incitements to violence.)

Zuckerberg talked to many people, both inside and outside the company, he said. “I knew that a lot of people would be upset if we made the decision to leave it up,” he told his employees. “But . . . I couldn’t get there. . . . Even with my personal feelings about the content. . . . I think the . . . policies that we have [and] the evidence here, overall, on balance—by quite a bit—would suggest that the right action for where we are right now is to leave this up.” The post had been an allowable warning about “state use of force,” he concluded.

Critics would later see no need for the hours of legalistic analysis that Facebook devoted to this process.

“We were obviously in a heightened moment around the murder of George Floyd,” says Arisha Hatch, of Color of Change. “And it was just a deeply problematic comment. Twitter took action on it and Facebook did not. And that is just one comment out of so many that Facebook has given an exception to Trump on.”

While Zuckerberg was still deliberating on the West Coast, Facebook’s Washington office had reached out to the White House, as Axios first reported. Facebook “raised concerns . . . and urged them to make a change, even if it did not violate our policies,” Facebook later told the Washington Post. (Facebook’s Stone declined to discuss Kaplan’s role with Yahoo Finance.)

Trump then called Zuckerberg. “I used that opportunity,” Zuckerberg told his employees, “to make sure that he understood . . . that I felt that [the post] was divisive and inflammatory and unhelpful and pushed on that.”

At 2:29pm ET, Trump issued an uncharacteristically exegetical post. It retroactively interpreted his original one in a way that would fall within the second of Facebook’s safe harbors, as outlined in the policy team memo. He had simply been warning that shooting was a possible, though undesired, consequence of looting, Trump maintained. “It was spoken as a fact, not as a statement,” he wrote.

The whole mind-blowing incident—culminating in a mini-summit conference between the CEO and the President of the United States—did not remotely resemble the image Facebook likes to present of its approach to content disputes: Dispassionate application of pre-existing rules to all comers.

3 possible scenarios

But what did this kid-glove treatment of Trump mean? Let’s make our own memo, posing three possible explanations.

Scenario A (consistent with the view of some critics): Kaplan was haggling with Trump over the post, because he was bending over backwards not to upset the president and Republicans.

Scenario B (consistent with a thesis discussed in a recent New York Times op-ed column by Ben Smith): Facebook was acting pursuant to an ongoing tacit (and corrupt) non-aggression pact with Trump, whereby Trump gives the company a pass on its antitrust issues and it gives him a pass on lies, hate speech, and incitements to violence.

Or, Scenario C: Facebook realized that, while the post was permissible under its rules, leaving it up would sow further division in the country and pour accelerant on years of smoldering frustration in the hearts of thousands of its own rank-and-file workers. So it tried to talk Trump into deleting it.

Frankly, we just don’t know which scenario is closest to the truth.

Roger Parloff is a regular contributor to both Yahoo Finance and Newsweek, and has also been published in Yahoo News, The New York Times, ProPublica, New York Magazine, and NewYorker.com, among others. He was formerly an editor-at-large at Fortune Magazine.

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