How a Facebook Employee Helped Trump Win—But Switched Sides for 2020

After the 2016 presidential election, Republican Party officials credited Facebook Inc. FB -0.18% with helping Donald Trump win the White House. One senior official singled out a then-28-year-old Facebook employee embedded with the Trump campaign, calling him an “MVP.”

Now that key player is working for the other side—as national debate intensifies over Facebook’s role in politics.

James Barnes left Facebook this spring, and said he is now dedicated to using the digital-ad strategies he employed on behalf of the Trump campaign to get President Trump out of office in 2020. Mr. Barnes, who had been a lifelong Republican, has registered as a Democrat and recently started working with a progressive nonprofit called Acronym, where former Obama campaign manager David Plouffe is on the board.

In a series of interviews over the past three weeks, Mr. Barnes discussed how he helped the Trump campaign leverage some of Facebook’s powerful tools and products to extend its reach. He talked about the pressure he felt behind the scenes, both from the Trump campaign and some colleagues at Facebook. His account sheds new light on Facebook’s role in the Trump campaign and what Democrats are trying to learn from it going into the next presidential election.

Mr. Barnes said he remains supportive of Facebook’s mission but is uneasy about the company’s influence on political discourse. One question that has nagged him over the past three years about his time at Facebook: “Did I actually do the right thing?”

Social-media platforms are sure to be a critical battlefield in 2020, with political spending on digital advertising expected to hit $2.9 billion, up from $1.4 billion in 2016, according to consulting firm Borrell Associates Inc. The Trump re-election campaign is already pouring money into Facebook ads, and Democratic candidates are ramping up.

Facebook has openly grappled with its approach to political advertising in the wake of revelations that Russian entities purchased digital ads designed to influence the results of the 2016 presidential election. It has also faced criticism for giving political campaigns access to sophisticated targeting tools, which in some cases allowed political actors to single out groups of users for misleading ads. In response, Facebook has made changes to slow the spread of misinformation and eliminated commissions for employees who sell political ads. The company is also considering ways to make it harder to target political ads to very small groups of people.

Another big change that came out of this reckoning: Last year, Facebook said it would no longer embed its employees with political campaigns, as Mr. Barnes had done.

Chief Executive Mark Zuckerberg has discussed his own soul-searching around whether Facebook should accept political ads at all, eventually deciding that it should and that it wouldn’t fact-check those messages as it does other content.

Facebook has played an increasingly large role in each of the last three U.S. presidential elections. In 2008, Barack Obama’s campaign was lauded for using Facebook to help reach young voters. In 2012, President Obama’s re-election campaign created an app that plugged into the Facebook developer platform and allowed users to prod friends in swing states to vote.

The company’s political ad strategy was initially modeled on its playbook for top corporate clients: Facebook employees offered on-site support to the U.S. presidential candidates who were considered the presumptive nominees for their parties.

Mr. Barnes joined Facebook’s political-ad sales team in June 2013 in Washington, following a stint at a digital consulting firm that worked for John McCain’s two presidential campaigns.

Like other tech companies, Facebook divvies up its political-ad sales team by party. Republican employees usually work with Republican clients; Democrats work with Democrats. Mr. Barnes was part of the team that dealt exclusively with Republicans.

In many ways, Mr. Barnes is the archetype of a Silicon Valley tech worker. He is analytical and measured. He is earnest and idealistic, describing on multiple occasions his desire to do good in the world. He fasts intermittently, sometimes going 72 hours between meals.

In other ways, he cuts against type. He grew up in Hendersonville, Tenn., in an evangelical family that attended church on Wednesday nights. His mother, Tami West, says he was an Alex P. Keaton type, referring to the Michael J. Fox character on the ’80s sitcom “Family Ties”: independent and staunchly Republican.

By the time the 2016 campaign was heating up, the developer platform used by the Obama campaign was mostly closed off, as part of a shift in Facebook’s strategy, but the company’s ad-targeting tools had grown more sophisticated.

Mr. Barnes became the Trump campaign’s go-to resource for figuring out how to maximize those tools. In April 2016, after a weekend at the Coachella music festival in California, he and his manager flew to San Antonio to meet with Brad Parscale, who became the Trump campaign’s digital director and is now overseeing the president’s re-election campaign. In Mr. Parscale’s office, and later at Bohanan’s, a local steak house, they discussed how Facebook could help the campaign.

One of the first things Mr. Barnes and his team advised campaign officials to do was to start running fundraising ads targeting Facebook users who liked or commented on Mr. Trump’s posts over the past month, using a product now called “engagement custom audiences.”

The product, which Mr. Barnes hand-coded, was available to a small group, including Republican and Democratic political clients. (The ad tool was rolled out widely around Election Day.) Within the first few days, every dollar that the Trump campaign spent on these ads yielded $2 to $3 in contributions, said Mr. Barnes, who added that the campaign raised millions of dollars in those first few days.

Mr. Barnes frequently flew to Texas, sometimes staying for four days at a time and logging 12-hour days. By July, he says, he was solely focused on the Trump campaign. When on-site in the building that served as the Trump campaign’s digital headquarters in San Antonio, he sometimes sat a few feet from Mr. Parscale.

The intense pace reflected Trump officials’ full embrace of Facebook’s platform, in the absence of a more traditional campaign structure including donor files and massive email databases.

The Trump campaign would give Mr. Barnes certain videos or images, such as a video of Donald Trump Jr. urging voters to help build the border wall. Mr. Barnes would experiment with different ways to display the ad. One might say “donate” while another would say “give.” Some videos would be vertical, others square. Buttons could be highlighted in red or green.

Each variation of the ad would be targeted to certain demographics. It could be as specific as 18-to-24-year-old men who visited the Trump campaign donation page and made it to the third step but never finished, according to Mr. Barnes. They tested all the variations and doubled down on those that raised the most money.

Trump campaign officials have said that some days the campaign churned out 100,000 separate versions of Facebook ads.

One official from the 2016 Trump campaign said it primarily relied on Mr. Barnes for troubleshooting and complained to Facebook about periodic technical issues that the campaign argued hurt its performance. The official, who is also working on Mr. Trump’s re-election campaign, declined to comment further.

Mr. Barnes’s Democratic counterparts at Facebook weren’t getting the same reception. Tatenda Musapatike, a former Facebook employee who worked with Democratic PACs and other independent expenditure groups in 2016, said she felt many Democrats held Facebook at arm’s length.

“For James, he’d suggest something and they’d say, ‘Sure, let’s try it,’” said Ms. Musapatike. “It was a battle for us to get anything accepted at a much smaller scale.”

Hillary Clinton’s campaign didn’t have Facebook employees stationed on site, according to people familiar with the campaign. One former Clinton campaign official said the campaign didn’t want to give Facebook employees “24/7 opportunity” to sell more ads by embedding with its staff. A spokesman for Mrs. Clinton didn’t respond to a request for comment.

Facebook referred to its prior comments on the embedding program. Last year, Facebook told lawmakers that it didn’t assign anybody “full-time” to either campaign and that it offered “identical support” to both sides.

Mr. Barnes said the experience was exhilarating but isolating. He was thrilled that the tools he helped build were working. But while he had a good relationship with Mr. Parscale and the campaign’s digital advertising director, Gary Coby, at times Mr. Barnes had reservations about Mr. Trump’s tone and rhetoric.

Still, Mr. Barnes said he felt he had a responsibility to help Facebook follow through on its commitment to assist candidates regardless of their politics.

“I used to describe my job as defending Trump to Facebook and defending Facebook to Trump,” he said.

Internally, Facebook staffers questioned the company’s role in politics. Sometimes they would ask why Facebook was offering assistance to the Trump campaign in the first place, according to Mr. Barnes and other former Facebook employees.

The critiques wore on Mr. Barnes. “It felt really isolating and lonely that I was at the nexus of all of this stuff,” he said.

During the campaign, Trump campaign officials frequently threatened to go to the press if Mr. Barnes and other Facebook employees failed to address problems to their satisfaction, he said.

For example, the Trump campaign needed a large credit line from Facebook, according to Mr. Barnes and others familiar with the situation. This issue posed special challenges. Facebook sometimes extends credit to a select group of digital agencies, but Mr. Parscale’s outfit didn’t qualify for a large line because it didn’t have a track record with Facebook, according to people familiar with the matter. The Trump team also wanted to pay for ads with a credit card, but Facebook’s transactions system wasn’t set up to handle payments of as much as $300,000 to $400,000 a day on a credit card, according to Mr. Barnes and others familiar with the matter.

As employees looked for ways to address the problem, Mr. Parscale texted Mr. Barnes to say Mr. Trump would go on TV and “say Facebook was being unfair to him” if the issue wasn’t resolved quickly, Mr. Barnes said. Eventually, Facebook came up with a fix.

Mr. Barnes said he felt responsible for protecting Facebook from these potential attacks.

Mr. Barnes said he ultimately voted for Mrs. Clinton. Ms. Musapatike said Mr. Barnes was in a funk after the election. “He had a difficult time reckoning with the impact of the election and his work,” she said.

A few days after the election, Mr. Coby directly praised Mr. Barnes on Twitter. In a now-deleted tweet, he said “@jameslbarnes of FB was a MVP.”

Being called out by name at a time when Trump supporters were being targeted by threats online was “terrifying,” Mr. Barnes said. Facebook’s security team called him with instructions for protecting himself and his privacy online.

Months later Mr. Barnes moved to San Francisco, joining a team that helped retailers like Macy’s use Facebook’s products. He tried to forget politics.

In December 2017, Mr. Barnes said, he was interviewed for nine hours by investigators for then-special counsel Robert Mueller. At one point they asked him if he had noticed any Russians hanging around the campaign, he said. “You wanna make a joke in that scenario,” he said, but “it’s not the opportunity to make a joke.” He told them he hadn’t seen Russians.

Mr. Barnes said he also spoke to the Securities and Exchange Commission about the company’s connection to Cambridge Analytica, which purchased data of about 87 million users of Facebook from a researcher without the consent of Facebook or the users.

Mr. Barnes doesn’t think Cambridge Analytica uploaded any illicitly gained Facebook user data to target ads, but that it wasn’t the norm for Facebook employees to ask for such details. Former Cambridge Analytica officials have denied using the data for the 2016 election. The SEC declined to comment.

At one point, in mid-2018, Mr. Barnes helped design Facebook’s much-touted “war room” for managing election integrity in the U.S. and abroad. Shortly before a press junket to showcase the effort, he said, two Facebook public-relations officials advised him to stay away from the event in case journalists raised questions about his role helping the Trump campaign.

That week, as he sat at his desk surrounded by empty seats, his frustration reached a breaking point. “[I’m thinking], when am I going to stop paying the price for this?”

In early 2019, Mr. Barnes took advantage of a Facebook perk called “recharge,” which gives employees 30 days off after they have been at Facebook for five years.

He considered going back to Facebook, but opted to take an active role opposing Mr. Trump’s re-election. In a private Facebook post on Aug. 5, he wrote that Mr. Trump’s slogan, Make America Great Again, was about “activating the deepest, darkest, soul of white nationalism.”

One of his calls was to former colleague Ms. Musapatike, who left in March to join Acronym as its senior director of campaigns overseeing the group’s online voter registration and mobilization programs. Chris Cox, Facebook’s former chief product officer, is now an informal adviser to Acronym and, people familiar with the matter say, one of its donors.

Ms. Musapatike warned Mr. Barnes that he might be viewed with suspicion at the organization because of his work for Mr. Trump. She vouched for Mr. Barnes with Tara McGowan, Acronym’s founder and chief executive.

Mr. Barnes decided he liked Acronym’s goal to beat Mr. Trump at his own game online, including on Facebook. This month, Acronym and its affiliated PAC announced plans to spend $75 million on digital ads. Mr. Barnes oversees Acronym’s analytics, helping the organization understand if its ads work.

Mr. Plouffe believes the former Facebook employee gives Democrats a secret weapon as part of a revamped effort to meet Mr. Trump on the social-media battlefield.

“He understands the most dominant platform in politics exceedingly well,” Mr. Plouffe said of Mr. Barnes. “He thinks differently from someone who grew up in politics a decade or more ago.”

By Deepa Seetharaman — Jim Oberman and Emily Glazer contributed to this article.