This story appears in the March/April 2017 issue of Playboy. Subscribe

One Friday evening before the 2016 election, Van Jones, the progressive lawyer turned CNN commentator, clicked go on Facebook Live to address more than 800,000 viewers, speaking for nearly 15 minutes without pause about a coming political and cultural upheaval he tagged #Trumpzilla.

“If you don’t understand the threat that a Donald Trump candidacy poses to the Obama coalition, I just don’t think you are paying good attention,” he said, his signature purple tie and round spectacles framed tightly in the shot. “We have to mobilize the entire country to recognize the dangers of giving a man like this the FBI, the CIA, the NSA, the IRS and the Pentagon to attack whoever he wants to.”

This wasn’t a last-minute plea; Jones said these words on April 29. (The post eventually earned 2,800 comments and more than 14,000 shares.)

Three days later, Jones again went live on his laptop to detail the candidate’s path to the White House, crystal-balling Trump wins in Wisconsin, Pennsylvania, Michigan and Florida. It would be a cruel understatement to say Jones’s forecast beat those of his colleagues in punditry. On Election Day, multiple media outlets drew on nonstop polling efforts and years of journalistic know-how to say Trump’s chances of winning were roughly the equivalent of an NFL kicker making a 59-yard field goal.

Jones smelled victory when others heard “grab them by the pussy” because he understands that in small-town America some jackass is always saying mean stuff. Jones knows this because he grew up on the septic-tank edge of a small town in the red state of Tennessee. In such places, when people say things you don’t agree with, you learn to shrug your shoulders and keep going.

Jones feels deeply at home in the middle, in other words. It’s why he’s friends with Newt Gingrich, whose conversations with Jones led the conservative to a turnaround on race that came out as “If you are a normal white American, the truth is you don’t understand being black in America.” It’s why Jones’s hard-right CNN cohort Jeffrey Lord admits, “We disagree on everything, but we talk to each other, not at each other, so, you know, God bless America.” As Anderson Cooper says, “There’s no doubt that Van has very strong opinions about where he is on the political spectrum, and he expresses those opinions, but he’s willing and able to walk in other people’s shoes in a way that makes us better every time we’re on the air.” 

Last fall, Jones brought an independent camera crew to the red heartland without telling his bosses at CNN and returned with a special program, The Messy Truth, on which he, a true-blue liberal, listens openheartedly to Trump supporters. CNN usually gets trounced in the show’s time slot, but the series premiere, which aired in early December, attracted 1.2 million viewers, exceeding that of its lead-in, Anderson Cooper 360, and almost beating Fox. 

Jones believes most liberal elites communicate contempt for conservatives and for small-town America. Some core articles of faith in the Democratic progressive coastal culture are just a stench in the nostrils of God, as he phrases it. This disdain, he says, is what cost the Democrats the election by just 79,000 crossover votes in three states, Wisconsin, Ohio and Michigan—a defeat made more painful by the fact that the Democrats used to be the party of bridge building and empathy. But try explaining to an urban liberal that some guy needs a hunting rifle so he can shoot a few bucks and butcher them to feed his family in case he can’t get enough work hours over at Family Dollar. At the same time, try explaining to that individual why African Americans are frustrated by our criminal justice system. Or why Latinos don’t think they’re being heard. Or why Bernie Sanders voters feel disrespected. 

I would trade in at least seven Black History Months for one Black Future Weekend.

Jones is 48, born into a time and place where every black church had a picture of Bobby Kennedy, JFK and Dr. King in the foyer or in the basement where Sunday school was held. These three martyrs were maybe just one step below Jesus, and they gave Jones the sense that you get only so many heartbeats to make your mark on this world. Jones went to public schools all the way through his undergraduate studies at the University of Tennessee at Martin. At the age of 21, he went to Yale Law School. The biggest body of water he’d ever seen was the Mississippi River, so he understands how other folks view things—folks who don’t drive Mini Coopers or listen to Radiolab. In fact, Jones is glad the whole world isn’t run by liberals, because if it were, everyone would know how many parts per million of carbon are in the atmosphere but nobody would be able to change a tire. We need one another. And yet, conservatives act as though America would be great if they could just eradicate all the horrible socialistic ideas, and liberals act as though the country would be better if they could just get rid of the two time zones between the Hollywood sign and Times Square. 

People often say Trump is breaking the rules of the old system, but Jones knows he’s simply following the rules of the new media. Franklin D. Roosevelt was the first radio president. John F. Kennedy emerged as the first television president. Barack Obama broke through as the first internet president. Their efforts were all dismissed at first but then became widely accepted, and so it is with our first social-media and reality-TV president. Trump seized on modes of culture and communication that others considered foolish. In reality television, the villain is the star. Simon Cowell on American Idol is the hero. Saying crazy stuff on Twitter gets you more followers. You wouldn’t have seen Trump coming if you watch TED Talks instead of Naked and Afraid. Jones gets that. But he also gets that reality TV and social media can be antidotes to our culture of bitterness if you back them up with intelligence and grace.

Jones lives in Los Angeles with his wife, Jana, who was born in Palmyra, Pennsylvania, and raised in La Vern, California. The couple has two young sons, the ones Jones became emotional about on live TV the night Hillary Clinton lost. Jones anguished aloud, “How do I explain this to my children?” That’s also when Jones spontaneously branded Trump’s ascension a “whitelash” against the Obama administration and a changing electorate, a comment that only magnified the Great American Divide. He wasn’t surprised by the strong reaction. From the beginning, he has built his reputation on “linguistic grenades,” as he likes to say. They’re what you deploy if you don’t have money or a marketing apparatus or lobbyists. You learn how to fight in close quarters with short phrases. Transparent creator Jill Soloway, who was a parent at the same L.A. preschool as Jones, says, “Van talks about building a ‘love army’ to fight hate, which can make you go, ‘Ugh.’ But with Van, it’s about the long game, love as a force. That’s the John Lennon game, that’s the Jesus game, and yet Van somehow plays it without the stink of a messiah complex.”

The first headlines Jones ever got were at Yale. After some racially inflammatory letters made it into the mailboxes of African American law students, he called for sit-ins and later led hunger strikes: “We have to shut Yale down to open it up” was the quote that stuck. Years later, as Obama’s special advisor for green jobs, enterprise and innovation for the White House Council on Environmental Quality—Jones hated that title; too many words—he was dismissed for accusing “white polluters” of dumping poison into neighborhoods of color and for saying of Republicans, “They’re assholes.” 

Today Jones sees his whole life as a focus group. CNN needs him in New York, but his office is in Oakland, where he runs the Dream Corps, a social-justice accelerator that tilts at the most formidable of windmills: cutting the prison population in half, teaching poor kids how to code, bringing solar energy to underserved neighborhoods. It is civil disobedience for the Uber generation, using skills and technologies Jones fine-tuned alongside, of all people, Prince. They met after the Purple One made a large donation to Jones’s Green for All project in 2008. It was supposed to be an anonymous contribution, but Jones demanded to see who was behind all those zeroes. They became the closest of friends and political co-agitators, something Jones revealed for the first time on CNN the night Prince died. Paisley Park was one of the only places Jones felt like a full, free human being as a black man. It makes him cry now, just talking about it. You get only so many heartbeats. 

Like Prince, Jones doesn’t do alcohol—he has never touched any intoxicants, he says—and he sees himself, as Prince did, as an Afro-futurist, the idea being that one’s “truest self” doesn’t line up with anything that already exists, and that that’s okay. It’s why we need to give young people of color the support and tools and inspiration and funding for a brighter tomorrow rather than dwell on the oppression of the past. As Jones says with that irresistible smile of his, “Harriet Tubman, I love you, but at this point, I would trade in at least seven Black History Months for one Black Future Weekend to discuss where we’re heading as a people.” 

On a December afternoon in San Francisco, Jones is heading to a private meeting with some prominent tech jillionaires. But first he needs to extract himself from the clutches of do-gooders demanding selfies after a talk he’s just given on employment opportunities for the formerly incarcerated. (“They can’t get student loans. They can’t rent apartments. They can’t get jobs. We’re wasting a ton of genius,” Jones told the crowd in rousing church tones.) It is rush hour and raining and the jillionaires are clear across town, but Jones makes time for every last prison social worker and parole officer. 

“You’ve had me weeping these last few months. You’re the only sane voice,” a woman in a United Way T-shirt tells him. She’s shaking a little as she captures the moment on her iPhone. 

“I appreciate that, sister,” Jones says, “but let’s move a little more into the light.” And he’s right. Bald was never so beautiful. The woman reaches up—he’s six-one and she’s not—and hugs him. 

“You gotta have high standards,” he says as another woman steps in for a photo, “because Facebook and Instagram—that shit is forever.”

Although he has a twin sister, Jones considered himself a loner and a misfit growing up. When you’re not in the popular crowd or even the unpopular crowd, you become radically independent of the approval of others, which gives you the advantage of not having to give a fuck. Jones’s mother was a high school teacher. His father was a middle school principal. It was a strict “yes, sir; no, ma’am” conservative upbringing, with not a lot of hugs or “I love you” moments. Jones found his salvation in comic books, specifically in the X-Men series and with Professor Xavier most of all. Here was a mutant who recruited other mutants to protect a world that hated and feared them. For Jones it was an allegory for the civil rights movement, and X-Men standards became his standards as he matured into a changemaker. 

Anti-mutant bigotry remains widespread, of course, and so Jones continues to rally and train X-geners from around the globe. On the light rail to the tech meeting, he talks about the many missions left to complete: fighting for clean-energy jobs, closing prison doors, providing low-opportunity youth with the resources and tools to become high-level computer programmers. Dream Corps has plans for teach-ins, house parties and concerts. Jones is toying with a virtual-reality version of The Messy Truth that would offer parallel immersive experiences so Democrats and Republicans can get a 360 on what the other side is up against. 

The jillionaire meeting is off the record, but aside from Jones telling the leaders of websites you probably use 200 times a day that jillionaires talking to jillionaires is a masturbatory exercise in feel-goodism that doesn’t actually change much, his message is essentially the same as it is everywhere these days: that we have a problem if Donald Trump can basically whip it out at the presidential podium and we still cover him. That we must wake up to the fact that the character of our nation and democracy has been called into question. That we need to be disobedient to the new reality of our government in order to be obedient to the demands of justice, to the demands of inclusion, to the demands of tolerance and fairness and compassion and love. That it’s essential to create ecosystems where magic can happen, because no matter how mean things get—and things could get plenty mean—we just have to keep going.