Part of Issue #10 of The Highlight, our home for ambitious stories that explain our world.

Chris Hughes was enraged.

The Facebook co-founder and I were leaving the Union Square subway station in Manhattan, which last fall was covered in ads for Twitter. The ads inside the station were one thing, but Hughes was seething that the campaign had extended outside, to the sidewalk.

“They stenciled it on — as though they haven’t colonized enough of our lives!” he kvetched, leading me out of our way to see the corporate graffiti. By that point, it had been washed away from the pavement so it was barely visible, but Hughes quickly emailed me a photo he had taken a few days earlier.

To Hughes, it was more evidence of the insidious power that Big Tech companies such as Twitter and the one he helped found in 2004 have gained in recent years. Twitter isn’t content to take over our minds and our screens, he worried. Now it was taking over the sidewalk, too.

Hughes — worth around $400 million, according to Forbes — is aware of his role in building this culture. He also knows that he’s hardly the first rich business leader to turn apostate and critique the capitalist processes that enriched him. But he’s unique in an important sense: He’s the first founder of a major tech firm to call for that firm’s dismantling.

Unlike his college roommates and Facebook co-founders Mark Zuckerberg (still at the company’s helm) and Dustin Moskovitz (now CEO of Asana, which makes project management software), Hughes, 36, is out of the tech game entirely, having departed the company more than a decade ago.

His earlier years as a megamillionaire were frankly cringe-inducing. He blew more than $4 million on his husband’s congressional campaign, which lost to the Republican incumbent by nearly 30 percentage points in a district President Barack Obama had won two years prior. He bought the New Republic in an attempt to turn around the venerable but ailing magazine, and when he tried to remove his handpicked editor, almost the entire staff resigned in protest. He unloaded the magazine shortly thereafter.

Since those debacles, Hughes has settled into a different niche, one that harks back to his long-ago role as Facebook’s house “empath.” He’s now a philanthropist, and a convener of other philanthropists and organizations. His full-time job, he says, is trying to craft a world “after neoliberalism” — one with a heavier hand of government and a smaller role for corporate power, one perhaps without Twitter monopolizing our sidewalks.

Hughes founded the Economic Security Project (ESP) with veteran activists Natalie Foster and Dorian Warren in 2016, and has increasingly focused on what they call an “anti-monopoly” agenda, encompassing traditional antitrust enforcement, offering “public options” on everything from banking to health care, and tighter regulation when firms can’t be broken up.

The agenda found its most public expression in May when Hughes in the New York Times called for the breakup of Facebook. In October, he and ESP went a step further: They announced a $10 million commitment from a variety of funders (Hughes included) to start an Anti-Monopoly Fund, which will invest in think tanks, researchers, and activists working on these issues. He is funneling money he earned from Facebook to end Facebook as we know it.

Hughes has emerged as a committed funder of a left-wing economic agenda, working with allies like Felicia Wong, president of the Roosevelt Institute, and Tom Perriello, the former Congress member who is now running US programs for the George Soros-funded Open Society Foundations.

By day, he works on the Economic Security Project and as a senior adviser to Wong at the Roosevelt Institute; at night, he’s studying for his master’s in economics at the New School for Social Research, famous for its heterodox, lefty-ish approach to the discipline.

The charitable interpretation is that Hughes has become a class traitor in the mold of Soros: a beneficiary of neoliberal capitalism who is now committed to breaking down the system that made him rich, bringing money to cash-strapped progressive organizations in the process.

The less magnanimous one is that Hughes is yet another plutocrat influencing politics, not unlike the Koch family or his ex-roommate Zuckerberg, who spent $100 million attempting to remake schools in Newark, New Jersey; or Tom Steyer and Michael Bloomberg in their attempts to buy the presidency. Such exercises of power by the ultra-wealthy, often cloaked as philanthropy, have come under increasing fire in recent years from the likes of writer Anand Giridharadas and Dutch journalist Rutger Bregman.

But Hughes and his team have had real successes. The Economic Security Project’s biggest initiative to date has been the “Cost of Living Refund,” an effort to dramatically expand the earned income tax credit and funnel more resources to low-income families. So far, the group and allied organizations have gotten legislation passed in California and Maine and count past and present presidential candidates, including Sen. Cory Booker and former South Bend, Indiana, Mayor Pete Buttigieg, as supporters.

But Hughes’s position is an awkward one to be in. He wields power because of his role as a plutocrat, even as he seeks to destroy that same power. Several anti-poverty advocates allege that Hughes has, at times, made some of the same errors as his conservative counterparts, privileging his pet projects over what experts in the field think should be top priorities, and pursuing incremental reforms at the expense of bolder measures.

As he amps up his war on monopolies, a natural question arises: Will Chris Hughes make a difference this time?

A rise through Facebook, and a fall

Hughes, the son of a paper salesman and a teacher in rural western North Carolina, has not been rich long. He attended both elite boarding school Phillips Academy Andover and Harvard University on scholarship. And despite not being able to code, he joined his college roommates Zuckerberg and Moskovitz when they launched a social networking site out of Kirkland dorm room H-33. He took on customer service, spokesperson, and product advice duties, providing a non-techie’s view of what features users would want. Facebookers reportedly nicknamed him “the empath.”

Unlike Zuckerberg and Moskovitz, he graduated from Harvard on schedule in 2006. He left Facebook a year later, at age 23, to join Barack Obama’s 2008 primary campaign, where he helped launch My.BarackObama.com, an early candidate-focused social networking site and oft-cited example of the technological edge that enabled the Obama campaign to topple Hillary Clinton.

Five years later, after a short period launching and running the startup Jumo (which sought to connect donors with charities and volunteering opportunities), he embarked on perhaps his best-known political endeavor: buying the New Republic.

It can be hard to remember now, but his purchase of the nearly century-old liberal magazine in 2012 was initially greeted with a burst of enthusiasm.

For most of the period from 1974 to Hughes’s purchase, the magazine’s principal owner was Marty Peretz, a New Left activist turned cranky racist who filled the magazine’s pages with a mix of truly great reportage and criticism, and his personal views on the “cultural deficiencies” of black, Latino, and Muslim people (in a particularly notorious post, he opined, “Muslim life is cheap, most notably to Muslims”). That the magazine had survived at all under the leadership of one of the most noxious figures in journalism was something of a miracle, and Hughes, with more financial resources and without Peretz’s sundry prejudices, seemed like a fitting savior.

“I have acquired a few sources at TNR from my sixteen years there, and they all seem giddy,” Jonathan Chait, by then at New York magazine, wrote. “So cheers to the 98-year-old institution.”

Not even three years later, Chait was penning what he called a “eulogy” for the magazine, suggesting that Hughes, in his view and that of many TNR old-timers, had destroyed it in a search for profitability and clicks. Hughes’s tenure ended with the mass resignation of his editors and writers indignant at his management — a professional defeat and personal embarrassment to a young businessman with a previously spotless record. George Packer wrote that the magazine suffered “a death by character flaw.” The novelist Cynthia Ozick wrote a poem about the incident concluding, “Thought and Word lay dead and cold.” Ruth Bader Ginsburg canceled her subscription. Hughes unceremoniously sold off the magazine in 2016.

Today he agrees with his critics’ indictments, calling his period as owner a “debacle.”

“It was by far the biggest mistake in my career thus far,” Hughes says. “I learned that what I would call smart, intellectual policy kind of journalism doesn’t need to have a business model. I was the last one to figure that out. Everybody else knew that. But my experience with Facebook and with Obama was to believe that these impossible things could be true, so I genuinely thought that we could find a sustainable business model for highbrow, erudite — the kind of journalism that the New Republic has historically done.”

Hughes’s other multimillion-dollar political investment during this period was more personal, though equally ill-fated. In 2014, his husband, Sean Eldridge, ran for Congress in New York’s 19th District, covering the northernmost suburbs of New York City. Eldridge, a veteran gay rights campaigner and founder of the investment group Hudson River Ventures, lost the race in a landslide, but not before Hughes and Eldridge spent $2 million to buy a house in the district, after forking out another $5 million on a house in the 18th District, where Eldridge first considered running; they then dropped another $4.25 million of their own money on the race, outspending the Republican incumbent 2-1. Today, the two spend most of their time in New York City.

Hughes declined to talk about the campaign, citing his marriage as off-limits. But he was happy to draw personal lessons from his time at the New Republic.

“I needed to work more collaboratively with the people around me,” he says. “I felt in the New Republic period that I had to figure out the answer to, ‘How do I find the business model for journalism?’ And I guess I thought I was gonna go up into some ivory tower and read enough books, and then I was gonna come down [with the answer]. And that’s not how the world works.”

And yet. More than a decade after leaving Harvard, he’s in school again, getting his master’s in economics at the New School. A major part of the Economic Security Project’s agenda is funding research, and Hughes is serious about his studies.

When I joined him for an evening class, the instructor, labor economist David Howell, made it clear that it would not be a traditional economics seminar. “The language of orthodox economics, and actually most economics, is about how the state intervenes,” he told the class of six, most from the New School’s urban studies master’s program. “As if there’s a blank slate and the economy starts out like Hobbes’s notion of mushrooms sprouting from the ground without any moms or dads or families or institutions or anything. It starts with a conception of the individual without any context.”

The students in his seminar make weekly presentations on their readings, and I visited during a week Hughes had chosen to present. The readings were on Speenhamland, a food aid program in 18th-century Britain whose track record has become a proxy battle about the effectiveness of welfare and cash assistance. It’s a debate of huge relevance to Hughes’s efforts to fund basic income programs.

“There’s a renewed movement today for a guaranteed income, and people continue to cite Speenhamland … as a confirmation of this view that humans are really just slothful and lazy,” he explained to his classmates.

After the presentation, a fellow student offered a modest critique of basic income, arguing that, unlike providing food directly, offering cash wouldn’t protect people against an increase in the price of bread.

Hughes shot back immediately. “You could peg it to inflation, though, just like a minimum wage,” he replied. That would solve the issue.

“You could,” his classmate responded. “I think that’s best practice,” Hughes concluded, and the discussion moved on.

Hughes was right — an inflation peg would prevent a basic income from eroding in value. But it didn’t really seem like a fair matchup, a master’s student not working in her native language debating a multimillionaire financing some of the world’s cutting-edge research on basic income and other programs where governments distribute cash.

Hughes’s push for basic income

“The time has come to design, develop, and organize for a Basic Income,” Hughes declared in the headline of a 2016 Medium post announcing the formation of a new group to promote the idea. “We aim to convene as broad and robust a conversation about these ideas as possible and to financially support people and organizations thinking through how a basic income might work, how we might pay for it, how to most effectively talk about it, and what a political roadmap might be to put it in place,” he explained.

Basic income, in its simplest form, is a straightforward idea: Everyone in a given country or state or city gets a set cash allowance (say, $1,000 a month) with no strings attached. It’s been a popular idea among philosophers and some economists for decades, and a version nearly passed in the US in the early 1970s. But in the 2010s, spurred by panic over job loss due to automation, it has exploded in prominence, fueled in no small part by activism from people like Hughes, former Service Employees International Union chair Andy Stern, and presidential candidate and entrepreneur Andrew Yang.

“I haven’t heard from Mark. That’s what everybody asks.”

Hughes and the Economic Security Project began with a series of conferences bringing together academics, think-tankers, and journalists to discuss the idea of a basic income and potential pathways to passage; I attended one in 2017.

Eventually, ESP’s interest in basic income resulted in the funding of a large-scale pilot program in Stockton, California, championed by the city’s young mayor, Michael Tubbs. But the direct political work of the group has shifted from giving cash, no strings attached. Instead, Hughes wrote in his 2017 memoir, Fair Shot, he and his allies decided to work within the existing American model of giving cash primarily to people who work, to reduce poverty and protect middle-class incomes in case of emergency.

Hughes frames this decision as a result of focus groups and other interviews he and co-founders Warren and Foster had across the country in 2017 as they “explored” the idea of a basic income. “People from every income and educational level, with all kinds of political beliefs and backgrounds, struggled to make sense of why anyone would support something like a basic income,” he writes. “The idea of money provided from nowhere and with no strings attached seemed nonsensical.”

“A dollar found on the street is different than a dollar loaned from a family member, and that dollar is still different than one earned through work,” he continued. “One working-class woman in Detroit put it plainly: ‘I just don’t understand where this money is coming from and why I would be getting it.’ Talking about money as an abstraction is something that seems to come from a place of privilege.”

So what does talking about money less abstractly — and with less privilege — look like? To Hughes, it means working within the existing work-based welfare state. “The optimal way to structure a guaranteed income would be through an expansion and modernization of the Earned Income Tax Credit,” he writes. “It is a complicated-sounding benefit and an awkward acronym, but boring methods can sometimes accomplish big-picture ideals.”

The tax credit is a huge program, distributing some $70 billion in benefits per year to Americans, mostly families with kids, and a robust community of activists and experts has sprouted up around it with plans to expand and modernize it. At the top of the agenda, for years, have been efforts to distribute it more regularly (say, monthly or at least biannually) and to expand the program for childless adults, who currently get a paltry benefit.

ESP’s campaign for a “Cost of Living Refund” — basically an expanded version of the earned income tax credit — has enthusiastically embraced both those policies, particularly regular, visible payments instead of payouts as part of tax returns. In June, both California and Maine passed proposals that ESP classifies as Cost of Living Refund bills; Maine’s would nearly triple the state EITC and offer the option to receive monthly credits. ESP was deeply involved in the push for both.

“As a partner with both us and others, [ESP’s] work is likely to contribute to significant EITC expansions,” Robert Greenstein, the head of the Center on Budget and Policy Priorities and a prominent advocate for anti-poverty programs, says.

ESP’s most distinctive policy, which was barely on the EITC policy agenda until Hughes and his group got involved, involves expanding the definition of work to include parental caregivers and students, so those groups get EITC, too.

In material terms, this is a rather small part of the picture. Elaine Maag, Donald Marron, and Erin Huffer of the Tax Policy Center analyzed the idea of adding caregivers and students in a recent report and estimated the cost at $70 billion over 10 years; the overall Cost of Living Refund would cost at least $2.5 trillion over 10 years, meaning “redefining work” accounts for less than 3 percent of the price of the proposal. “There aren’t that many caregivers of children under 6 that aren’t working — so they’re mostly already getting the EITC,” Maag explained in an email.

But the idea has become a preoccupation, and specialty, of ESP all the same. Adam Ruben, who runs ESP’s Cost of Living Refund campaign, readily concedes that the idea wasn’t on the agenda before ESP started pushing for it. “There’s a lot of people who we work with who are in those spaces who are trying to help caregivers, or trying to help students,” he says. “We will call them up and go, ‘Tell us about what you’re doing. We want to understand what the fight is there.’ And then we say, ‘We have this idea that actually could help family caregivers through the EITC.’ … And they go, ‘Oh, that’s interesting. Hadn’t really looked at that before, but that seems really consistent [with what] we’re trying to do.’”

Inserting new ideas is a big part of what advocacy and research groups are supposed to do. But ESP’s insistence on this specific idea rubs some other advocates the wrong way. For years, momentum in child poverty circles has been building for a policy called a child allowance, which would offer all or almost all families a set check per child (say, $300 per month for young kids, and $250 per month for older kids), with no strings attached or work requirements. An accomplished group of scholars proposed the idea in a paper for the Russell Sage Foundation, a major National Academies of Sciences report floated the idea this year, and a bill supported by most congressional Democrats would make it a reality.

A couple of advocates for that policy expressed frustration to me that Hughes and ESP are putting so much energy and money behind a separate policy to help families with kids, one that Hughes happens to talk up in his book, rather than on the policy where the majority of the coalition for an expanded safety net has focused its energy. Tellingly, they declined to go on the record for fear of alienating a coalition ally.

Hughes rejects the idea that this is some idiosyncratic preference of his and his team’s. “People have been talking about [defining caregiving as work] for a long, long time, first off. Let’s be clear,” he said in a meeting with Warren and Foster. “Particularly feminist economists, a long line of them, have been talking about expanding the definition of work. ... In some ways, it’s us trying to amplify those historic lines of argument.”

Foster agrees, and argues that focusing on rewarding caregivers doesn’t necessarily distract from the effort to expand the child credit. “We do it in allyship with people trying to expand the child tax credit,” she said. “We think it’s a great tax credit and it should be ‘both/and’ not ‘either/or.’”

If some critics think Hughes’s group is insufficiently attuned to political realities, others think it has become far too timid in the face of them. “I have always felt that unconditional cash is promising because it contrasts with the EITC,” says Marshall Steinbaum, an assistant professor of economics at the University of Utah who worked on ESP-funded projects at the Roosevelt Institute during his time as a fellow there.

From Steinbaum’s vantage point, Hughes started as a promising figure who could fight to replace the EITC with an unrestricted cash benefit not tied to work, but after some immersion in the think tank world, he lost his nerve. “He should not have given up on UBI [universal basic income] as thoroughly as he did,” Steinbaum says.

Hughes against the monopolies

“I haven’t heard from Mark. That’s what everybody asks.”

Hughes and I were chatting about the reception to his proposal to break up Facebook, which was illustrated in the New York Times by a diptych of Zuckerberg’s and Hughes’s faces. The op-ed began with Hughes recalling the last time he and his college roommate and co-founder hung out.

“Mark is a good, kind person. But I’m angry that his focus on growth led him to sacrifice security and civility for clicks,” Hughes wrote. “The government must hold Mark accountable.” He specifically suggested forcing Facebook to undo its purchases of WhatsApp and Instagram in 2014 and 2012, respectively, and allowing those services to exist as independent companies competing with Facebook rather than acting as part of its empire.

Hughes knows his arguments for taking monopolistic power seriously aren’t original. In his piece, he cited Barry Lynn, who has been sounding the alarm about corporate power for decades and was eventually forced out of the think tank New America as a consequence, as well as younger anti-monopoly legal scholars Lina Khan and Ganesh Sitaraman. Khan’s 2016 paper “Amazon’s Antitrust Paradox” helped spark a revitalized conversation about using antitrust law to target major tech companies.

It’s a conversation that Hughes and ESP joined relatively late. Hughes’s entry had an “et tu, Brute” quality — one Facebook founder turning on another and threatening his old roommate’s fortune — that gave the critique sharper teeth. But he’s still joining a crowded field. When ESP started exploring basic income, it was still a fringe idea in most political circles; by contrast, as they plan to dip into anti-monopoly work, they do so after the frontrunner for the Democratic presidential nomination, Sen. Elizabeth Warren, had already rolled out a plan to break up big tech companies (Hughes has stayed neutral in the primary to date; he donated tens of thousands to Hillary Clinton and associated PACs in 2015 and 2016).

But Hughes sees his work on the matter, including convening his $10 million Anti-Monopoly Fund — backed by the Hewlett Foundation, Omidyar Network, and Soros’s Open Society Foundations — as much broader than antitrust. (Omidyar Network is a partner on Vox’s Open Sourced project.)

“I come from the labor movement,” Dorian Warren, the ESP co-chair, says. “This thing had been gnawing at me: What is the other side of the equation in terms of worker power? It’s taking on corporate power in all of its manifestations.”

That means not just breaking up big, powerful corporations but also using other regulatory tools to weaken “monopsony,” when a handful of corporations control the labor market and are able to drive down wages (as recently happened to chicken farmers), and creating government-run “public options” in everything from health care to banking (perhaps by running a basic savings and loan out of the post office) as an alternative to corporate power.

The Roosevelt Institute’s Felicia Wong, who relies on Hughes as a senior adviser as well as a funder, positions him and ESP as central in a broader effort to repudiate neoliberal economics — rejecting a focus on markets and privatization ahead of building government capacity — and craft an economic agenda that can be bolder and leftier than what the Obama administration achieved.

“Roosevelt started to do this work with Hewlett and Omidyar around what an economic paradigm ‘beyond neoliberalism’ would look like,” Wong says. Hughes ate it up.

“He got super, super, super interested, and then it really started to deepen.” Now, she and Hughes work “extraordinarily closely,” she says, talking several times a week about cash and the broader anti-neoliberal project alike.

“I guess I thought I was gonna go up into some ivory tower and read enough books, and then I was gonna come down [with the answer].”

I asked Hughes how he came to terms with the inherent contradiction of trying to wield power he gained through his wealth and entrepreneurship to dismantle the economic system that produced that wealth.

“It’s been really important to us from the start that ESP be an organization that’s much bigger than me individually,” he said. “But it’s still true that, you know, the funding comes from wealthy people or, you know, foundations and institutions with power. And so it’s important to name that and accept the responsibility that comes with that.”

Foster chimed in that she sent Giridharadas’s book Winners Take All, a critique of how the wealthy use philanthropy as a smokescreen, to ESP’s funding partners. “Those with means should be challenging the system. It’s like, read this and let’s continue to be in dialogue on this,” she said. “Let’s challenge inequality together.”

That, in essence, is the dilemma posed by Chris Hughes. He is a very smart multimillionaire philanthropist. He is an unusually self-aware multimillionaire philanthropist. But he still is, and behaves like, a multimillionaire philanthropist.

“We’re in a unique time,” he notes, “where those of us who are funding individuals and organizations have a pronounced responsibility to think about what privilege that brings.”

Dylan Matthews is a senior correspondent and lead writer for Future Perfect at Vox.

Annie Tritt is an editorial photographer based in New York City. You can find other stories by Annie here.