Sheryl’s Political Headwinds, Thiel’s Sway, & Gates+

Sheryl Sandberg
Ex-Meta COO Sheryl Sandberg. Photo: Kimberly White/Getty Images

When I talk to progressive fundraisers, I often ask them to posit their dream principal, or white whale—someone whose fortune they would love to direct toward their own philanthropic or political ends. There are revealing answers, like Stripe co-founder Patrick Collison, and obvious ones, like MacKenzie Scott. But the question can actually become more elucidating when it is inverted: Who is the figure whose wealth they want to avoid?

The world of philanthropy and political donations, after all, is often rather risk-averse. Advisors, who make big bets with other peoples’ money, are highly attuned to the possibility that a particularly controversial ultra-high-net-worth donor could alienate their peers or taint an organization. The one name that has come up more than any other in these conversations is Sheryl Sandberg.

That is why I found it hard to not marvel last week as I read Sandberg’s announcement that she plans to dedicate more of her time to philanthropy after stepping down as Facebook’s first and only chief operating officer. Sandberg once had unimpeachable bonafides in the Democratic establishment: Larry Summers protégé, Obama-era feminist icon, presumptive Clinton cabinet member. She was reportedly ready to leave Facebook for Washington, in 2016, had the election gone the other way. Instead Sandberg became an avatar of Facebook’s work with the Trump campaign, and an increasingly toxic personage for the left as she managed the company through scandal after scandal. Democratic leaders, including Clinton, turned on Facebook and on Sandberg. Liberal politicians began to talk about Silicon Valley as if it were Big Oil or Big Tobacco. In what I thought was an era-defining moment, Elizabeth Warren, for one, announced that she would not take any money from Big Tech executives, just like she wouldn’t accept support from leaders at fossil-fuel companies.

The notion that Sandberg would become a Cabinet secretary, never mind an elected official, is mostly dismissed by insiders as a pipe dream. Sandberg is obviously brilliant and knows her way around politics, yet I wonder whether she’s fully aware of the dynamic she’s walking into as she looks to return to Democratic and philanthropic circles. When it comes to politics, in particular, a big check from a controversial donor can become a P.R. nightmare. Attacking the contributor is part and parcel of the modern campaign playbook. Look at Democrat Chesa Boudin going after G.O.P. mega-donor Bill Oberndorf for funding the recall campaign against him, or Jim Lamon’s new ad this week tying Blake Masters to Peter Thiel. Warren blasted Pete Buttigieg for raising big money in a Bay Area wine cave, then took fire herself, after her super PAC cashed a $16 million check from Karla Jurvetson. Fairly or not, progressive fundraisers have to be mindful of activist criticism from the left.

Optics aside, there are also some progressive operatives who would genuinely wrestle with the ethical implications of taking Sandberg’s money, even if they could remove her fingerprints. Does a check from Sandberg help to launder the profits of a business that capitalized on partisan outrage, that arguably exacerbated the teen mental health crisis, or was weaponized by genocidaires in Myanmar? I previously reported at Recode that Color of Change, a progressive advocacy organization, declined in 2019 to take a check from the Chan Zuckerberg Initiative, Mark Zuckerberg’s personal philanthropy with his wife, because it viewed his money as tainted. Others believe the contradictions inherent to accepting Facebook money are similar in some ways to, say, accepting Sackler money to finance a new wing of the Met. “That’s one way to know who not to support,” one Democratic bundler, a Facebook critic, told me. “I wouldn’t give money to anyone who takes money from her.”

But purity politics are a luxury in a complicated world. At the end of the day, most Democrats just want to win—and getting funding for the left can trump more abstract hangups. Tara McGowan, a top operative who is now raising money for her network of progressive newsrooms, Courier, is as harsh a critic of Facebook leadership as there is on the left. But she told me that she would welcome a Sandberg check for her organization. “The insights she has into the most powerful information distribution network in the world (that she helped to build)—and especially now without the restraints of working within the company—would very likely make her contributions to our work and movement more valuable than most,” she said.

The call gets tougher, of course, as the check size gets bigger. And Sandberg, a rare non-founder and non-C.E.O. billionaire, is still in the early stages of flexing her political muscles. Thus far, she has given only about $2.5 million to disclosed federal campaigns and groups over the last two decades—not a huge number, considering Sandberg was worth about $1.6 billion earlier this year—including the $400,000 or so she sent Clinton’s way in 2016. It’s possible that the hundreds of millions Sandberg has placed in donor-advised funds have gone toward some quasi-political efforts—DAFs don’t have to disclose who gets the money—but her only regular big political checks tend to be the $100,000 she sends to an arm of EMILY’s List, which she did in 2018, 2020, 2021, and again this past April. Notably, Sandberg didn’t donate anything publicly to Joe Biden in 2020 or to the Democratic National Committee, the first time she didn’t contribute to the Democratic nominee since Al Gore ran for president in 2000. Instead, her political checkbook has been aimed at less headline-generating causes, like a tax proposal in her hometown of Menlo Park. 

This is the paradox for Sandberg: She is eager to get involved in the public arena at a time when substantial portions of the public view Facebook negatively. But Sandberg’s accomplishments as an iconic, enormously successful business executive may eventually outlive the stench of Facebook’s past scandals, especially with time, distance, and—most importantly—money, which has a way of winning out. I have no doubt that more moderate Democratic candidates wouldn’t think twice about cashing her checks if the dollar figure is big enough. Michael Milken, who was convicted of securities fraud in 1989, has since become one of the world’s most renowned conference-throwing philanthropists. Bill Clinton bounced back from impeachment and a sordid affair by reinventing himself as a leader on global health. Even Bill Gates, once reviled as a monopolist and—like Sandberg—dragged before Congress, was transformed through good works into an almost saintly philanthropic idol. 

So I think Sandberg will, over the long term, be accepted back into the Democratic establishment. There is rampant speculation regarding what Sandberg will do next in politics and philanthropy. In the short term, she will have to contend with some backlash from the left. She can possibly leverage her accumulated years of goodwill with women’s health organizations, which may provide a launching pad into adjacent domains. With the right political finesse, the right staff, and the passing of time, Sandberg can probably restore her name and begin making bigger political moves. In the meantime, there are plenty of dark-money vessels for Democrats to hide a six-figure check from a controversial tech executive, current or otherwise.

Thiel Transcendent

The other major news in big-money world was Donald Trump’s totally-expected, nevertheless significant endorsement of Peter Thiel disciple Blake Masters on Friday afternoon. One year ago, when I first wrote about Masters’ nascent bid for the U.S. Senate in Arizona, his candidacy was very much a longshot: Sure, he had the backing of Thiel, but he had basically zero political relationships in Arizona, was likely running against current state officeholders, and had campaign infrastructure.

These days, it is probably fair to call Masters the frontrunner for the G.O.P. nomination. Masters, who turned a self-assigned notetaking gig in one of Thiel’s law school classes into a de facto chief of staff job at Thiel’s family office, is incredibly well-financed, thanks to $13.5 million in super PAC checks from his former employer. The latest polling (from way back in April) showed Masters in third at 19 percent, but the Trump seal of approval is likely to give him a big boost—even if the endorsement statement itself was characteristically overzealous, describing the 35-year-old head of Thiel Capital as “one of the most successful businessmen and investors in the country.” Quite a high standard.

I’ve argued before that Thiel’s kingmaking ambitions have been overstated in the press—at the moment he seems to care more about electing his two protégés, Masters in Arizona and J.D. Vance in Ohio, then becoming the next Sheldon Adelson. And for Thiel, Masters’ candidacy is probably the more important of the two. As I reported in April, a person close to Trump was reliably told that Thiel had delicately expressed to Trump that if he could only call upon one endorsement favor, it would be for Masters. The favoritism is apparent in Thiel’s donation decisions, too. While P.T. gave $10 million to super PACs behind both of his two proteges, he only awarded an extra $3.5 million to Vance after he secured the Trump endorsement in the final weeks of the Ohio primary. In Arizona, P.T. cut another $3.5 million check to Masters well before the endorsement, and well before the August primary. This time Trump followed Thiel, rather than Thiel following Trump.

Gatesworld on the Potomac

Lastly, I wrote last week about the annual convocation of The Giving Pledge, the Gates-organized, high-octane philanthropy conference which just met in-person for the first time since 2019, in Ojai, California. Meanwhile, just a few days later, another high-altitude, highly-secretive confab came together in-person on the opposite coast: Bilderberg.

Bilderberg, whose annual conferences were historically a backchannel for political and business elites to discuss the great power struggles of the time, has evolved into a conclave to promote globalism, capitalism and democracy. But it remains an object of fascination for conspiracy theorists and media observers, alike. Held over the weekend in Washington, the first time in the U.S. since 2017, this year’s invitees from Silicon Valley include politicos like Thiel; Thiel’s college friend and LinkedIn co-founder Reid Hoffman; Thiel’s Palantir co-founder Alex Karp; and the uber-politically connected former Google C.E.O. Eric Schmidt. Another regular is Sam Altman, the Y Combinator wunderkind who now spends his time on heady issues like nuclear energy and artificial intelligence, and who attended this year for the first time since 2016. Wall Street sent its representatives, of course, as did the Biden administration. Georgia Democratic grassroots hero Stacey Abrams, who I was surprised to learn sits on the Bilderberg steering committee, apparently missed this year’s event.

The conference itself is highly secretive—Chatham House rules are respected, details don’t leak, and it reflects the sort of backroom foreign-policy conversations that might have happened at Bretton Woods or Casablanca in an earlier era but now are increasingly difficult to execute. The more interesting of the dozen topics this year, according to the group, included Russia and Ukraine; the “fragmentation of democratic societies”; “disinformation”; and “disruption of the global financial system.” All worthy topics, of course, and ones that reflect a central conceit for us here at Puck—that among the upper echelons of America’s elite, the conversations taking place between the power centers of Washington, Wall Street, Silicon Valley, and Hollywood are increasingly one and the same. Bilderberg is one of the places where that agenda is debated and set.