One evening early last October, a crowd gathered around the deep end of a black-bottom pool in the Hollywood Hills. There were probably 100 people there, most of them balancing plastic cups of pinot noir and platefuls of gouda and prosciutto and thick, artisanal crackers crammed with nuts or dried fruit.

Leonardo DiCaprio, in various shades of gray, was leaning against a nearby bar. So were Paris Hilton, Ashton Kutcher and Glenn Close, who had come with her dog, which was little, of indeterminate breed, probably a rescue. There was also a venture capitalist or two, the head of partnerships at Snapchat, attorneys, finance bros, several writers and producers, and the co-founder of an online retailer that specializes in men’s grooming products. These were not, by and large, celebrities, but they could afford to spend an evening with people who were – and had paid as much as $2,800 for the privilege. They were smart, or smart-adjacent, successful or very successful, media savvy, fashionable, nicely coiffed.

They were there because they felt a responsibility, and it was fun, and it might be useful – to be seen, to have a reputation for being politically engaged – and because they hated Donald Trump, viscerally, his smallness and meanness and lack of culture, and they hated that he was the president and that they were tied to him by dint of being American.

The main host of the fundraiser was Michael Kives, a former Hollywood agent who had represented Arnold Schwarzenegger, among other stars. In 2016, Kives (pronounced “key-vess”), together with his friends Darnell Strom and Jordan Brown, raised from their vast networks of famous and wealthy people almost $5m for Hillary Clinton’s presidential campaign, collectively making them among Clinton’s top-ten “bundlers” – people who raise and collect individual donations on behalf of political candidates.

Facebook Twitter Pinterest Michael Kives and Kate Hudson at LACMA last September. Photograph: Stefanie Keenan/Getty Images for Snap Inc.

“The first day Hillary announced, they were really aggressively going after their network,” said Stephanie Daily Smith, who was the Clinton campaign’s West Coast deputy director. “Anyone who was young Hollywood. Anyone they knew on the East Coast. They were getting people that were their clients.”

In 2020, Kives, Strom and Brown are likely to play an even bigger role in the campaign. If a mainstream Democrat is the presidential nominee, they’ll probably raise more money than they did in 2016 – they really want to crush Cheeto Mussolini. If it’s Bernie Sanders – whom the bundlers blame for costing Clinton the election – they’ll focus on House and Senate races, and they’ll be indispensable: Sanders, despite his huge following, would be a yoke around the neck of every vulnerable Democrat in every middle-of-the-road state or congressional district in the country, and those Democrats will need more tony, backyard fundraisers than ever.

What makes Kives, Strom and Brown unusual is not the money per se. It’s that they’re three decades younger than they’re supposed to be and that they think differently - not just about the horse race, but the ways in which politics interacts with markets and technology and a borderless, popular culture created and promulgated by digital natives.

They liked Buttigieg, and if he didn’t make it this time there were still the next 10 election cycles to look forward to. But they’d also raised money for Corey Booker, and they had flirted with Kamala Harris and even Beto O’Rourke. The candidate wasn’t really the point. What mattered most, besides beating Trump, was that the next president do things that previous presidents had ignored or been unable to do or even conceive of.

They did not imagine – the way, say, Joe Biden did – that the next president would be able to rewind the clock and return the country to its prelapsarian self, before Trump and MAGA and the daily burlesque that was the GOP and its tens of millions of tribespeople. They thought the next president had to do big things – tackle the climate crisis, reform health care – but, more than that, rethink the government’s relationship with a complex, interconnected world that did not respect the old tempos. “Our brains easily understand linear growth, but it’s hard to wrap our minds around exponential growth,” Brown said in an email.

Genomics, mass auto, driverless cars, flying taxis and AI’s that write legal briefs and teach high-school biology will not only make us more efficient but change how we relate to each other, what it means to be a citizen and an American, how we make money – how we imagine ourselves. They wanted systemic change – Electoral College reform, an end to gerrymandering – and they seemed intrigued by candidates who grasped that something seismic was happening in America and across the world, that we were between economic orders, that we needed a new vernacular. “If we can shore up our democracy and make … the economy work more equitably, and prepare for innovation that’s coming quickly, then that’s a net positive and a huge improvement over the past three decades,” Brown said.

•••

Six months earlier. I had arranged to meet Kives at his house at 11am. It was a Friday in mid April and a wan, white-blue sky stretched across the Los Angeles basin. There was a black Tesla in the driveway and I could hear sprinklers and leaf blowers and a tennis ball somewhere being whacked. Kives’s wife, Lydia, answered the door. I recognized her from an article in Vogue about their wedding, which Bill and Hillary Clinton, Sheryl Sandberg, Elon Musk, Cory Booker and Jordan’s Prince Hussein had attended, and at which Katy Perry had sung Hava Nagila.

Kives wasn’t there, and Lydia asked if I wanted coffee or water, and I took a seat at the end of the dining-room table, while she called her husband - to see when he’d be home, to make sure I wasn’t a lunatic. A moment later, he texted me: “Racing back - sorry!” He suggested we start on FaceTime. “Forgot to put this in my calendar,” he said. “I’m so sorry.” I was slightly wounded but noted that he’d said sorry twice. While he talked – he had just come from a “birthday thing” for Kate Hudson, who had been his first big client – he stared ahead, at the cars and stop lights. Every few seconds, he would glance down at me. I felt like I was crouched beneath the passenger seat of his car, staring up at his chin.

Facebook Twitter Pinterest ‘He was an amazing networker:’ Kate Hudson, Michael Kives and Jessica Alba. Photograph: Stefanie Keenan/Getty Images for Baby2Baby

At the time, the thinning of the Democratic field had yet to start. In LA, there were fundraisers every night. The candidates would spend a few days shaking hands in Iowa City or Manchester, New Hampshire; fly to DC to cast a vote; jet out to California, head to someone’s house in Brentwood or the Palisades, give a speech, rake in the cash; and fly back to the voters. In 2016, Democratic bundlers coalesced early around Clinton. They’d known her forever. This time, they were holding back. They’d been burned last cycle - they couldn’t imagine Trump beating Clinton - and they wanted to see who had The Stuff. “There’s a lot of energy in the party, in Hollywood, in the country, I think, for this next generation of Democratic leaders,” Kives said.

Kives’s road to becoming a big wheel in the Democratic money machine began in June 2001, when he was an undergraduate at Stanford. Bill and Hillary Clinton were flying in for Chelsea Clinton’s graduation. Kives admired Clinton - his intelligence, his ballsiness, that determination not to let enemies or idiots get in the way of whatever he wanted. He wanted to meet him. He had to. So he hatched a plan that involved covering Clinton for The Stanford Daily. And that led to a spot on the Clinton entourage, which led to a conversation, a friendship, a professional identity. He became a Clinton guy, and he seemed motivated by a general faith in the Democrats and a fidelity to the former president and first lady, and a belief that knowing important people would lead to good things.

Like a job at the mailroom at CAA. Before he was bumped up to assistant. And then agent. The story he liked to tell was about Kate Hudson. So, Hudson comes into CAA, and the question is: Who’s going to represent her? Sure, she could go with an established agent. But then Kives, the newbie, makes his case: “You should go with me because it’ll help me,” he says. She looks at him like, Who the fuck are you? And he says: See, an older agent doesn’t need you. But I need you, and if you give me this chance, I’m going to owe you forever, and I’ll never stop working to prove it. Boom! She signs. In 2018, many deals later, Kives left CAA – where “a good but not great agent can clear $1 million, even $2 million a year,” a producer told me – to launch an investment-advisory firm called K5 Global (the 5 stands for entertainment, tech, sports, business and politics). Warren Buffet put out a statement singing his praises.

“He was an amazing networker,” a Hollywood director said of Kives. “There’s literally no one important anywhere, and I mean fucking anywhere, who’s not connected to him by one or, at most, two degrees of separation.” As if to underscore this point, there was an oil painting hanging in Kives’ living room – a still life, not bad, definitely not a Gauguin, with the number 43 in the bottom, right-hand corner. As in the 43rd president of the United States, who took up painting after he left office. Kives explained that he was friends with his daughter Barbara Bush.

His network, like that of Strom and Brown, was a work of art. It stretched across generations and continents. It was a tree-like atlas of the last two decades of his life, and it was gorgeous. It could raise campaign cash. Or close deals. Or lay the groundwork for Web 3.0. It was the future, and the key to doing it well, said Natalia Brzezinski, the CEO of the Brilliant Minds Foundation, which hosts an annual symposium in Stockholm that includes some of the most influential people on the planet, was not to think about networking qua networking.

“Think about who can I help, what two people can I bring together to create something cool,” said Brzezinski, whose husband, Mark, was the son of former National Security Adviser Zbigniew Brzezinski. “What is the bigger picture and how can we … innovate a better world?”

•••

In 2008, Jordan Brown was on a charter plane from New York to Vienna with Ivana Trump, Katy Perry, several models and Fran Drescher. People were smoking, jumping on seats and playing Truth or Dare. Brown was four years out of college and running Drescher’s non-profit organization, the Cancer Schmancer Movement, and they were flying to the Life Ball, one of the biggest HIV charity events in the world. At the ball, Brown met a young black man who was travelling with Bill Clinton’s entourage – Darnell Strom.

Strom’s father had been raised in a one-bedroom house, without plumbing, in a small town in South Carolina. His mother came from the projects in Oakland, California. They had met, in 1968, at San Jose State University, and then Strom’s father was drafted and sent to Vietnam, and they started seeing each other in 1970, after he returned. Strom had grown up in a middle-class neighborhood nearby. He loved politics. He remembered being a six-year-old in 1988 and watching the Democratic convention on television. “My favorite thing ever was the balloon drop,” he said.

Facebook Twitter Pinterest Darnell Strom in 2015. Photograph: Todd Williamson/Getty Images

Strom said he’d wanted to attend a historically black college, so he went to Florida A&M. After graduation, he took a job at the Clinton Foundation in New York. There, he found himself in a rarefied universe teeming with heads of state, tech barons, oligarchs and celebrities. It was like a graduate seminar in how big things got done – major deals, market-moving press releases, a tête-a-tête between a Saudi billionaire and someone’s chief of staff.

In 2006, while traveling with Bill Clinton, Strom met Kives in a hotel lobby in Kigali, the capital of Rwanda. By then, Kives was already at CAA, but he had stayed close with the Clintons and was advancing the trip. He had to make sure everything ran smoothly – checking travel routes and venues, lining up local media, coordinating with everyone on the ground. Kives and Strom hit it off.

By the time Strom met Brown at the Life Ball in Vienna two years later, Strom had been promoted to the Clinton Foundation’s “millennium network director”, which entailed recruiting wealthy donors. Brown, watching Strom juggle the Clinton entourage, was impressed. Everyone wanted a moment with Clinton, and the ball was like this swirling stew of faces and voices and loud peals of laughter, and Strom had to control access – to make sure the right people and no one else got to speak with the former president without creating a scene. “I was like, ‘This guy’s amazing,’” Brown said. “‘He’s just making shit happen.’”

Strom started spending more time in Los Angeles for work. Lots of donors. He got to know Kives better and then Kives’ agency, CAA. “That kind of transitioned into, ‘You seem to be an interesting guy who rolls in these worlds that could be interesting to us,’” Strom said. CAA wanted him to come on board. It wasn’t totally clear what he’d do. They’d figure it out. So he made the leap. He started by helping CAA’s clients – famous athletes, musicians, actors and directors – “figure out what they wanted to do in the nonprofit space, the cause space and also some folks who were interested in some issues in politics” – meaning it was his job to suggest possibilities, forge connections, see where everyone’s brands aligned. That’s what he loved – figuring out how to connect people, in Hollywood and beyond.

The old guard at CAA was always a little leery. Why waste time on anyone outside movieland? That’s what they did – movies. Strom made it work. After nine years at CAA – where he represented Nobel Laureate Malala Yousafzai, will.i.am and YouTube co-founder Chad Hurley, among others – he jumped to the United Talent Agency, to run the new Culture and Leadership Division. Bold move. On the totem pole of Hollywood agencies, UTA was a notch below CAA, but UTA was offering Strom something big: The chance to create a new division, to make connections with everyone. To be a “culture-shaper,” as Brown liked to put it.

“Entertainment has expanded the type of voices that are in the room,” Strom told me as we sat in his office in Beverly Hills. On the window ledge was a photograph of Strom and Bill Clinton greeting Nelson Mandela in Johannesburg.

“Yes, it can be traditional, entertainment figures,” he continued. “It can be folks who are coming in from fashion, art and design who are interesting that now have platforms thanks to social media. It can be social activists. It can be health and wellness gurus. It can be chefs. It can be all of these things that have been at the forefront of driving our social culture, but now they’re being woven all together.

When I asked Strom what had led him to this juncture, from the ordinariness of California suburbia to the uppermost echelons of the global elite, he said, “Curiosity.” It was canned, of course, in keeping with the indefatigably happy talk of the 1 percenters – who were not necessarily happy so much as wary of upsetting anyone – but there was some truth to it. He had considered going to law school, and then settling in the Bay Area, and then running for office. This was what ambitious lawyer-politicians were supposed to do – this was what the Clintons had done.

But that felt staid, so he deferred, and then he tried to defer again. Then he did what he wanted to do. He immersed himself not in the world of politics but of politicians, in Manhattan, with the connecters. The magnetic, trumpet-like, neon buzz of The Big Game. He did this because it was like being at an amusement park.

He followed his curiosities, and it led all the way here.

•••

By early last summer, one could detect, among the bundlers, the setting in of a low-level nervousness. Like a persistent cough. Or a tick. The field was still fragmented.

Jordan Brown, like Kives and Strom, was spending a lot of time hop-scotching between powerful and often famous people. In July, he attended an intimate dinner for Kamala Harris, who was still running for president, at the home of his former boss, the record executive and film producer Scooter Braun. A few months later, he was at the Buttigieg fundraiser in the Hollywood Hills, and in early November, he flew to Des Moines with his friend, the singer-songwriter Ben Harper, who was headlining a concert for the mayor. In December, he went to the Democratic presidential debate, at Loyola Marymount College, in Los Angeles, with Sophia Bush and some of the big-wigs at Politico.

Jordan Brown (center) with Pete Buttigieg (right).

I met Brown for lunch in June at the San Vicente Bungalows, in West Hollywood. The SVB, which used to be a gay bathhouse, which used to be a cluster of bungalows for day laborers laying the railroad tracks to the ocean, was the new elite’s response to the old elite. It was airier, greener, chaise-lounge-ier than the older, whiter, maler, mahogany-wood-panelled, dry-martini hangouts downtown, like the California Club and the Jonathan Club. There was an ethereal quality to the Bungalows; being there felt like floating through the numinous afterglow of the paparazzi flash bulbs.

Brown grew up in Taft, at the base of California’s agricultural Central Valley. When he talked about his adolescence and early adulthood, he toggled between foreground and background, between the story of himself and the story of post-cold war America.

Since forever, Taft had been an oil town. Spacious, one-story houses; tidy streets; a bustling downtown, with a theater, restaurants, a florist and a barbershop; schools; Friday night football; a healthy working class that mostly worked at Aera, the oil-production company. Then the oil and the jobs tapered off. They built a minimum-security and then a maximum-security prison. The old storefronts were subsumed by bail-bondsmen, The Dollar General Store, liquor stores, pawn shops. The kids who graduated from Taft Union High School enlisted in the Army and were shipped to Afghanistan or Iraq; or they worked for the county; or they left; or worse. Opiates seeped in. There was a school shooting. In less than a decade, Taft had been transformed into somewhere generic and sad. “It is absolutely a microcosm of what’s going on in the country,” Brown said. When Brown got into Stanford, the Taft Daily Miner published a front-page story about it, above the fold.

At the start of sophomore year, right after the 9/11 attacks, he was lugging boxes up a stairwell, in his dormitory, when he met Kives, who, even then, was “a force,” Brown said. Brown’s mom, Jana, who was with him, said, “That guy’s either going to be your best friend or your worst enemy.” The next summer, Brown, who had never known anyone Jewish, visited Kives at his home, in Winnipeg. He recalled spending Shabbat with Kives and his parents. “So gregarious,” he said. “Love them.”

In his senior year at Stanford, Brown took a class called History of US Intelligence. At the end of it, he was recruited by the CIA. But then, like Strom, he deferred one life so he could pursue a life in politics. He did a stint on John Kerry’s presidential campaign in Oregon and wound up as a delegate at the Democratic National Convention in Boston. (Strom and Pete Buttigeg were also there, although none of them knew each other at the time.) “I thought I was going to go work in the White House,” Brown said. Then Kerry lost. He moved to DC anyway. “I didn’t really know what I was going to do,” Brown said. He worked at a nonprofit. He was curious about big questions: the post-post-industrial economy, urbanization, the conflict between technology and democracy. That led to the Cancer Schmancer Movement, in LA, and then to the Summit Series, in Miami, and then to XPRIZE, where he was “senior director of visioneering,” back in LA.

He wasn’t ascending any particular career ladder. He was zig-zagging between ladders. That was his career. On the side, he launched a boutique, political-strategy agency that advised celebrities, founders and influencers on “innovative advocacy and philanthropy goals,” according to his LinkedIn profile. He started working for Scooter Braun. He expanded his Hollywood footprint. Like Kives and Strom, his job was to connect people.

“I try to be that bridge,” Brown said. “I’m in rooms often with really powerful people in tech and media and entertainment, and they talk about politics, and often I have a different take. That’s based on where I grew up.” He didn’t buy the argument, popularized by Thomas Franks’ 2004 book What’s The Matter With Kansas?, that rural voters had been duped into voting for Republicans. “People always say, ‘Why are these people always voting against their interests?” Brown said. “But we don’t really know what drives people.”

Since 2000, Brown observed, presidential elections have been decided by a handful of voters, mostly in the Upper Midwest. Every election felt like a Manichean showdown. This spiralling out of control would either persist, until the losers of elections stopped conceding they had lost and the democracy was derailed, or we would forge a new consensus that revolved around new alignments. That would require a leadership that could transcend the past while not abandoning it, that could forge a new compact between the government and the governed rooted in the American mythos. “You can lie, cheat or steal when you’re at the margins,” Brown said, “but then demographics catch up, and you have to broaden your coalition, because you can’t keep winning by 15,000 votes in three battleground states.”

•••

Late on the night of 3 February, I texted Brown to get his take on the still-unfolding mess in Iowa, where the first-in-the-nation Democratic primary had just happened. A coding glitch in the app used by the state Democratic Party to report caucus data earlier in the evening had malfunctioned, and election officials were not releasing results. “Just got home from kives house,” Brown texted back. “This is a huge gift to Biden and horrible for Pete. He’s gonna fucking win Iowa and won’t get the lift. He missed three hours of wall to wall ‘HOLY FUCK’.”

As it turned out, Buttigieg did win Iowa, and the slow drip of the news cycle, with election results coming in batches, seemed to help him. By Wednesday, two days after Iowa, he was surging in New Hampshire, which was scheduled to vote the next Tuesday. “The following that he has garnered, regardless of how this turns out, is really becoming a political movement,” Brown said. After Iowa, #CIAPete and #PeteTheCheat trended, briefly. But that was mostly beside the point. Buttigieg was 38 and gay, and he often talked about his husband, “the love of my life,” on the trail, and he had won in rural and suburban precincts.

“All this work is happening, at the base level, in culture,” Brown said. “Then, it’s organizing. Then, it’s political. It’s movement-building. But it starts with exposing people to people who are different, ideas that are different, giving them space to not be afraid of that difference and not feel judged for their reflexive responses.”

It was easy – tempting – to make fun of all this. The platitudes, the summit-speak, the endless yammering about convening and collaborating and networking and architecting. “The elite has always had a rationale for its privilege, and it’s generally because it’s better for everybody - whether it’s an aristocratic elite or a Gilded Age elite or whatever,” William Deresiewicz, the author of Excellent Sheep: The Miseducation of the American Elite, told me. “They always have that rationale. If you go to Aspen or probably Davos, this is the story the elite always tells itself. They’re full of their good intentions. Their rule is great for everybody. In fact, their rule isn’t even rule.”

But there was a danger in trying to fit this new, American elite onto the Procrustean bed of every elite that had come before it. The early elite was defined by family – by blood –and one’s membership in it was immoveable. Then, in the early 20th century, with waves of immigrants pouring into Ellis Island, the old, WASP guard had to make room for the Jews and Catholics forcing their way into the Ivy League and the white-shoe firms and the highest reaches of government, academia, banking and the law. This somewhat liberalized elite was defined by accomplishment.

Then, in the early 21st century, with the old political, geopolitical and economic institutions in retreat, a new elite emerged out of war and recession and social unrest. It was defined, mostly, by the people it knew. By its network. That enabled the new elite to grow, to scale, in directions and with a velocity that previous elites could have never fathomed, but it also made for a flimsier perch. One was not born into the new elite, and, once admitted, one could not be sure one would die in it. One resided at the very top of the sprawling, kaleidoscopic, international, gig economy, and one’s place in the world was never guaranteed. The new elite was perennially anxious, and it was embarrassed by its status. It denied it. It felt retrograde.

“Quite frankly, I think what it is that I do is the opposite of [elitism],” Strom said in our interview. “It’s like, how can I bring as many people into the fold? Elitism is something that is very exclusive.”

A few weeks after meeting Brown at the San Vicente Bungalows, I stopped by the house he shares with his partner, the artist Paul Rusconi, and Rusconi’s 10-year-old, twin daughters, in Lake Hollywood. Up the road, the Hollywood sign, with its 45-foot letters, loomed over the cluster of houses sprinkled across the hillside. Inside, there were paintings by Andy Warhol, Damien Hirst, Man Ray and Kehinde Wiley, who, in 2017, was commissioned by the Smithsonian to paint Obama’s portrait. There were also several works by Rusconi, including a large, yellow-ish painting that featured a model and was done with nail polish on plexiglass.

“I am very allergic to the term ‘elites,’” Brown said. “It feels almost Dickensian to me. I don’t accept that there are or should be classes of people. I get that that may be naive.” He was sitting cross-legged on a couch in the living room. On the other side of the sliding-glass door, near the pool, a few chickens had gathered and were pecking at the ground in the sun.

On Sunday, Buttigieg got out. The next day, Amy Klobuchar, the senator from Minnesota, also ended her presidential bid. Biden had just trounced everyone else in the South Carolina primary, and it was now a two-man race – the former vice president versus Sanders. If only Mike Bloomberg, waging his $300 million, Super Tuesday air war, would give up.

Brown was hardly ecstatic - Biden felt like a let down - but he seemed relieved that the party was coalescing around one of the more centrist candidates. “I don’t think that there’s anyone who would argue that a Biden presidency will be transformative,” he said. “I don’t think even he is arguing that. Trumpism is strong and embedded, and I think the pendulum swing of another ideologue is more than the country can handle.”