In the spring of 2004, when Facebook was little more than an online portal for students at Harvard University to stalk their crushes, senior Pete Buttigieg was the website’s 287th user.

Fifteen years later, the relationship between the world’s most influential corporation and a rising candidate for the Democratic presidential nomination has gotten, in Facebook parlance, complicated.

On Monday, Bloomberg reported that billionaire Facebook founder Mark Zuckerberg had passed along the résumés of two individuals seeking positions on Buttigieg’s campaign staff. The hires in question, data specialists Eric Mayefsky and Nina Wornhoff, were recommended to campaign manager Mike Schmuhl by Zuckerberg and his wife, Priscilla Chan.

The campaign has aggressively fought back against allegations of even a whiff of impropriety, noting that Zuckerberg’s emails were sent at the applicants’ request, and that Buttigieg’s team had received more than 7,000 job applications between Buttigieg’s breakout appearance on a CNN town hall in March and his campaign’s official launch the following month.

“Other people we have gotten staff recommendations from: former Presidents, civil rights leaders, members of Congress, Pete’s high school teacher,” tweeted Lis Smith, Buttigieg’s communications director. “We make staff decisions on how to build the best team in politics, which I’m proud to report we have!”

But as some fellow Democratic presidential hopefuls call for the government to potentially break up large tech companies, and Facebook’s leadership continues to defend the company’s position that politicians should be considered exempt from its rules regarding hate speech, harassment and false advertising, the relationship between Buttigieg and Silicon Valley is under renewed scrutiny.

Speaking to voters in Nashua, New Hampshire, on Thursday, after this article was initially published, Buttigieg said that the company’s ad policy was “a mistake,” and said Facebook has a responsibility to pull false advertising from its site, political or otherwise.

“I believe that the breakup of big companies is a remedy that should be on the table,” Buttigieg said, adding that he doesn’t think that such a proposal “should be declared in advance by a politician.”

For Sen. Elizabeth Warren, whose political life has been defined by curbing corporate power, the appearance of any coziness between Zuckerberg and a political campaign—particularly one that’s hot on her tail in Iowa—is bad enough as it is, regardless of the fact that the two staffers hired were not in political roles.

“My views on Mark Zuckerberg are pretty clear: He runs a company that has too much political power,” Warren told a gaggle of reporters on Monday, when asked about the résumé exchange. “They already have way too much influence in Washington and they are helping drive every conversation in a way that will protect Mark Zuckerberg and his company but that undermines our democracy. That is why I have said I think it’s time to enforce the antitrust laws that are already on the books—we need to break up these big tech companies.”

Warren has pointed to Facebook’s outsized influence and alleged disinterest in preventing the spread of fake news as evidence that the company has failed to learn the lessons of the 2016 presidential campaign, when pages dedicated to sharing fake news—sometimes with the assistance or orchestration of the Russian government—targeted voters in the lead-up to the election.

“Here’s the thing, Mark,” Warren tweeted last week, after Zuckerberg gave a defensive address at Georgetown University. “Trump isn’t just posting a lie on his own page for his own followers. Facebook is accepting millions of dollars from Trump to run political ads, including ones with misinformation and outright lies… Facebook already helped elect Donald Trump once. They might do it again—and profit off of it.”

By one measure, at least, Buttigieg is far and away the preferred candidate of Facebook’s employees. According to a review of Federal Election Commission data by The Daily Beast, the mayor of South Bend, Indiana, raked in $23,095.36 in donations from Facebook employees in the first six months of 2019, a sum that includes checks written by some of the company’s most senior employees. David Marcus, the former president of PayPal and current head of Facebook Messenger, donated $2,800 to Buttigieg the day before he officially launched his campaign; Naomi Gleit, senior director of the growth, engagement, and mobile team at Facebook and the company’s vice president of “social good,” also donated $2,800.

Other high-level donors from Facebook’s upper ranks include Maz Sharafi, global head of marketing for WhatsApp ($2,000), Victoria Grand, WhatsApp’s vice president of policy and communications ($2,000), and Elliot Schrage, the company’s former vice president of global communications, marketing, and public policy who led its response to the Cambridge Analytica scandal ($2,000).

In comparison, the rest of the top tier of Democratic presidential candidates have raised far less money from Facebook employees over the same period—although Sens. Warren and Bernie Sanders, who have both called for the government to take antitrust action to break up Facebook, have each actually received more individual donations from the company’s workers. In the first six months of 2019, Sanders raised $6,084 from 88 Facebook employees, while Warren raised $9,362.80 from 65 employees, and former Vice President Joe Biden raised $1,500 from seven people.

(For the curious, President Donald Trump has raised $383.91 from 12 separate donations over the same period, all made by the same solitary Facebook employee.)

Some of that pocketbook enthusiasm is likely rooted in Buttigieg’s discomfort with the idea of breaking up Facebook, which his rivals say has become too powerful and monopolistic. After Harvard acquaintance and Facebook co-founder Chris Hughes published a piece in the New York Times calling for the company to be broken up, Buttigieg told the San Jose Mercury News that while Hughes “made a very convincing case” that no company “should have the type of power that… these tech companies have,” he would prefer implementing “a spectrum” of regulations over the industry.

Some preference may lie beyond policy, however. Buttigieg, the youngest candidate in the field, has called for increasing the government’s technological literacy, pointing to congressional hearings in 2018—which featured Zuckerberg—as an example of “people in charge of regulating a very powerful force demonstrating that they had no concept of what it was they were in charge of overseeing.”

Politicians, Buttigieg told the Mercury News, “need some kind of literacy in these technologies, what they mean and more importantly what they can do, in order to regulate properly,” although he added that the critique was “not necessarily an age thing.”

Buttigieg’s working relationship with Big Tech extends to before his run for the White House. When Zuckerberg set off on a much-hyped tour of the United States following Trump’s inauguration, he joined Buttigieg in his hometown, streaming live video from the dashboard of Buttigieg’s car as the pair toured the city and discussed proposals intended to lure tech startups to revitalize downtown South Bend.

“Like everybody else, I’ll be very interested to hear what he makes of what we’ve shown him,” Buttigieg said at the time.

But Buttigieg’s campaign denied that his support from Facebook employees and the tech industry more broadly means he’s any softer on Silicon Valley.

“Since the beginning of the campaign, we’ve built a top-tier operation with more than 430 staff in South Bend and around the country,” said national press secretary Chris Meagher in a statement. “The staffers come from all types of backgrounds, and everyone is working hard every day to elect Pete to the White House.”

Zuckerberg, meanwhile, told reporters on Monday that passing along the résumés “shouldn’t be taken as an endorsement.”

“When a number of colleagues who I’d worked with at Facebook or my philanthropic foundation were interested in working there, they asked me or my wife Priscilla to send over their résumé, so I did that,” Zuckerberg said on a press call on Monday, during a conversation about election security. “I think that this probably should not be misconstrued as if I’m deeply involved in trying to support their campaign or anything like that.”