In its June 2017 issue, The Atlantic published a long essay about Richard Spencer by Graeme Wood. Wood, now a national correspondent for the magazine, went to school with Spencer at St. Mark’s School of Texas, an all-male prep school in Dallas, in the 1990s. “Richard Spencer is a troll and an icon for white supremacists,” the article subtitle reads. “He was also my high-school classmate.”

We learn that Wood remembers “little to admire and little to despise” about his former classmate—merely the “featureless mediocrity” of a kid who “passed his classes but didn’t excel,” misquoted Shakespeare in his high school yearbook, and was, improbably, friends with one of the few black students at St. Mark’s.

Wood’s profile resembles a number of other recent reflections on Steve Bannon, Stephen Miller and Julia Hahn, all of whom spent time in liberal institutions before becoming associated with Trump. Penned or consisting of statements by former colleagues or classmates, these articles make an implicit promise to their readers: that, having known them before they became Breitbart staff writers or the face of the alt right, the author will be able of pull back the curtain and shine a light on a demonic, or at the very least a Machiavellian, mind. As Peter Maass puts it in his recent essay about Julia Hahn for The Intercept, the goal was to assemble “the puzzle of her journey to the alt right” in order to answer the question posed succinctly by one of Hahn’s college classmates on Facebook: “WTF happened???”

Such investigations have rarely fulfilled their promise: Maass ultimately acknowledges that “the mysterious thing about Julia Hahn is that there is any mystery at all.” But then why write the article? Perhaps this is the more complicated, and interesting, question that is raised by this burgeoning genre. Why do liberals find illiberal sensibilities so “mysterious” in the first place?

Last fall, I began writing a reflection on Richard Spencer of my own, having become friends with him in grad school. The process of writing the piece wore me down. In the end, it became as much an investigation into my own social and political impulses—as solipsistic as they are charitable—as an attempt to share my observations about a man who had emerged from relative obscurity to become an international totem of hate.

A shockwave went through the core of liberal America when Donald Trump was elected president precisely because so few liberals ever bothered to understand, let alone reckon with, the deeply held beliefs of Trump’s base. But the same dynamic plays out on a smaller, more intimate scale all the time.

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I met Richard Spencer in April 2002, at a three-day open house for students admitted to the University of Chicago’s Master of Arts Program in the Humanities (MAPH). I capped off the long days of classes and meetings in a smoke-filled bar near the university’s campus, excitedly discussing literature and philosophy over pitchers of cheap beer with a couple dozen people I’d just met. I was 26 and had been having a rough time trying to make a living as a journalist in post-9/11 New York: Chicago promised a place where ideas, not status or money, were the primary social currency. It didn’t take much to sell me on the program.

At an information session on Saturday morning, I struck up a conversation with a young man sitting next to me, whose name was Richard. Like me, Richard had moved to New York after college. He had interned at the Brooklyn Academy of Music, and was interested in studying philosophy and opera—he particularly loved the work of Wagner. He was contemplating a Ph.D.

In September 2002, Richard and I were just two of the hundred or so students in our MAPH cohort, and we became friends. He was something of a dandy, fond of ascots and all things Viennese, and he spoke with an almost British lilt to his voice. I learned that he had grown up in Texas and gone to college in Virginia.

I’ve always had a high tolerance for idiosyncratic personalities. I prided myself on being accepting of those who held radically different views than my own—my closest friend in New York had been a Republican and evangelical Christian, while I was an atheist whose political beliefs veered toward socialism—but I’d never met anyone who said the kind of things Richard would say. I remember him making some brazen comments at the program’s Friday night social hours, and over beers at the pub, like the time he insisted that the Mexican laborers who worked on his family’s land in Texas relished their menial jobs and had no desire to climb out of poverty, or when he unabashedly asserted that if a man spends time talking to a woman at a bar then she is obligated to go home with him. He was a good conversationalist, though—with me anyway—and he seemed to respect me. And he had a wry, patrician sense of humor. His delivery was always mannered—his tone, to my ears, always tinged with irony. He referred to the MAPH soccer team as “landed gentry” and the business school’s as “new money.” He once approached me in the weight room at the university gym and, with a little wink, said, “I just come to watch.”

Not everyone saw Richard the way I did, least of all the women in the program. Many people found him arrogant and condescending. Some found him creepy. One woman, a Jewish musicologist and performer, told me this fall that her first impressions of Richard were that of an “insecure, petty, emotionally stunted” man who “never withheld his contempt for me, as he would try to undercut any statement I made.” Another woman, then 22 and just out of Ohio State, described him as “pompous and dismissive of any views other than his own.” Yet another, a classically trained cellist who bonded with Richard over music, said she was appalled when he suggested booing at concerts if he didn’t think the musicians were up to snuff. He publicly bragged about being one of the twenty or so students in our program who’d received a half-tuition merit scholarship, and rumors circulated early in the fall term that he had audibly exclaimed, to no one in particular, that he needed to get laid.

I was a few years older than most of the other students, including Richard, and for the first time in my life I felt I was in a position to impart my relative wisdom, to offer a little guidance to an awkward, socially insecure 24-year-old. But there was a selfish motivation, too: I wanted everyone I liked to get along, and despite his sometimes-shocking statements, I liked Richard.

One day on a stroll across the university’s quad, I told Richard that he was alienating people. He listened intently and seemed troubled by the news. We didn’t speak of it again, but as the year progressed he became warmer, less aloof, and was soon a reasonably popular guy. He ingratiated himself with the most social students in the program and got invited to the parties they threw. In my photos of Richard and our classmates they are smiling, drinking, hanging out.

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We were a diverse set—Jews and Muslims, Africans and African-Americans, gay men and women, older students burnishing their skills for specific professional purposes and kids right out of college preparing for careers in academia—studying everything from Shakespeare to South Asian municipal architecture. Richard was friendly with several people in the program who would not identify as white. He regularly played basketball with a black woman who, recalling her time on the court with Richard, noted that “you don’t play basketball with just anyone; it’s something you share with people you trust, want to know better, with whom you have mutual respect.” In October 2002, Richard threw a Halloween party at the spacious apartment he shared with two International Relations master’s students, and invited everyone in our program. He dressed up as a Roman emperor and was proud of the decorations—cobwebs, plastic spiders, jack-o-lanterns. I went as a proletarian.

Richard and I were part of a group that often stayed late at the pub having precisely the kinds of discussions I fantasized about when I applied to Chicago, debating free will and parsing the finer points of Marxism and the concept of a nation-state. In retrospect, I’ve often wondered if we were having two separate conversations. There were others in our group who held some unpopular views—a libertarian Ph.D. candidate in the history department, studying early modern Europe, for instance—but unlike Richard, they eventually drifted toward the center. Years later, that historian would marry a woman with a Ph.D. in social work.

Toward the end of our MAPH year, Richard and I discussed going into business together. We talked about opening a small, independent bookstore and press, with a café upstairs. We’d publish books by unknown but talented, contrarian authors, and maybe a magazine. The café would be a place where people of all ideological leanings could talk politics and art, literature and philosophy, not unlike the popular campus coffee spot, Classics Café.

I thought he’d be an agreeable partner. We’d worked together on a variety show for our classmates earlier in the spring, and Richard had been disciplined and exacting, but also, in his way, kind. We were going to sing a duet of Bonnie “Prince” Billy’s “I See a Darkness.” The song begins:

Well, you’re my friend (That’s what you told me)

And can you see (What’s inside of me)

Many times we’ve been out drinking

Many times we’ve shared our thoughts

But did you ever, ever notice

The kind of thoughts I got?

But during rehearsals I had trouble carrying the tune and Richard suggested that we work together on a short skit instead—UChicago: The Musical, a parody of Chicago, in which Richard dressed in drag as the program’s co-director, the philosophy professor Candace Vogler, and sang “The Name On Everybody’s Lips is Gonna Be Candy.” Our classmates remember the event well. “Richard played Candace, and did so with flair,” one recalled. “He was actually hilarious, and eerily accurate.” Another said, “He imitated her body language perfectly, and the vocal inflections, to boot.”

The bookstore idea never extended beyond some beer-fueled conversations, and soon after graduation Richard left Chicago for a Ph.D. program in intellectual history at Duke University. I eventually returned to New York and resumed my journalism career. Occasionally, we’d catch up over the phone. In December 2005, he visited me for a few days in Brooklyn. He was thinking of leaving his Ph.D. program, he told me. He asked for my advice on starting a career in journalism. He slept on my couch and drank all of my soy milk.

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Richard finally left Duke at the end of 2007. He called me to talk about establishing himself as a “public intellectual,” an idea that was bandied about a lot when we were at Chicago, where it was seen as a viable alternative to a life in academia. He’d had a stint as the literary editor at The American Conservative but was fired, evidently on account of his extreme beliefs.

Not knowing this at the time, I got him a freelance gig writing for AWEARNESS, a left-leaning political blog sponsored by the fashion designer Kenneth Cole, where I was the chief writer at the time. I introduced him to the blog’s editor as a smart, conservative voice who could offer a “different perspective.” Richard was grateful. That summer he wrote a post on the term “moneybomb” entering the political lexicon and followed it with a post decrying rent control, and another lauding Vladimir Putin. That was about it for his affiliation with AWEARNESS. He had landed a job as the managing editor of Taki’s Magazine, a libertarian webzine whose tagline is “Cocktails, Countesses & Mental Caviar.” It was a better fit for Richard.

In August 2008, Richard moved to Brooklyn, settling just a few blocks away from me in Park Slope. By then I was used to his provocations, and even his politics—but I had yet to see him as racist. That started to change soon after he arrived in New York. We were standing on the sidewalk in front of my apartment on a hot summer afternoon when Richard said something blatantly disparaging about non-white people—no smirk this time, no chance to read him as ironic. I don’t remember what he said exactly, but I do recall my reaction. “You know that my girlfriend is black, right?” I asked him. He stared at me, and then sputtered, “Really?”

After that conversation, I began to distance myself from Richard. I saw him on the street occasionally and we would stop and chat, him often rhapsodizing about the virtues of purity and physical strength. Once, I saw him while I was out running. “I don’t do that shit,” he said. He preferred lifting weights.

Not long after the 2008 election, we got into an argument over email about Michelle Obama. Richard insisted that she was illiterate, and had only achieved her station in life through affirmative action. He even sent me her college thesis from Princeton to “prove” it. I read the paper and wrote back to say he couldn’t possibly be serious. Richard’s reply was curt: “I don’t think you read it.”

I stopped talking to Richard after that, but our friendship didn’t end for good until 2010. He had launched a new website, AlternativeRight.com. Figuring it was nothing more than pseudo-intellectual charlatanism, a vanity project for Richard’s bloviations, I didn’t read it until March of that year, when FrumForum, the blog managed by former George W. Bush speechwriter David Frum, posted an article about it. The article, titled “The ‘New’ Racist Right,” took a damning view of the site, noting pointedly that “they’re going to be white nationalists, but by God, they’re going to be a little fancy about it.”

Richard posted a link to the piece on his Facebook page, celebrating the coverage. His followers responded with an outpouring of noxious comments. One referred to blacks, Asians and Hispanics as “human-shaped objects.” I joined the fray, writing, “Do any of you ‘human-shaped objects’ have any friends who don’t look, dress, talk, and think pretty much exactly like you do? What’s next for your ‘provocations,’ lynchings?” Soon I was being attacked from all sides—one person suggested I was a racist in denial, ashamed of my white heritage; another called me a “self-hating liberal” and “comedy gold.” I called Richard on the phone, furious, not just with the people who were attacking me but also with Richard. I told him that if he had any respect for me, and for the time we’d spent as friends, the least he could do was tell them to stop. He obliged. “I suggest that we bring this discussion to a close,” he wrote on his Facebook page. “David and I were friends back at UChicago, 7-8 years now. We’ve only been in contact occasionally since, but I can vouch he’s a decent guy.” After a few more comments, the bitter exchange ended. But with it went any fondness I felt for Richard.

At the end of 2010, Richard left New York for Whitefish, Montana, where he would mount his own private war on immigration and a multicultural United States, through his writings on AlternativeRight.com and as the executive director of the National Policy Institute, a white nationalist “think tank.” I followed his career with morbid interest from afar, occasionally watching his sparsely attended speeches on YouTube, reading his diatribes about “cuckservatives” and Muslims on Facebook, and sharing with mutual friends any press he received during his years-long ascent to where he is today.

Whenever one of us saw him profiled or quoted in a publication, we’d send the link around, expressing at first a sense of disgust over the person Richard had become, and then dismay that he was now the most famous member of our class. Over time, as the coverage grew in both volume and prominence, the responses in our email chain diminished. Our dismay had morphed into a kind of helpless fatigue. Everyone in our group was sick of hearing about Richard, long before November 2016.

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In November, as I began writing this piece, I reached out to Richard on Facebook Messenger to give him an opportunity to comment; it was the first time we had been in contact in almost seven years. Minutes later he replied and asked for my phone number, so that when I called him he would be sure to answer. He said he’d been getting death threats and was leery of calls from unknown numbers. We talked on the phone for nearly an hour. He asked about my work, if I was still in Brooklyn. He seemed genuinely interested, and I’ll admit that it felt nice—despite it all—to hear the familiar voice of an old friend.

We soon moved on to the alt right, the D.C. conference, and Richard’s evolution over the past fifteen years from a young academic to the face of a movement that has been likened to the Nazis and the Ku Klux Klan. But Richard gave me little more than alt-right talking points, dismissing many of my questions with a patronizing chuckle: the people who’d Sieg Heiled him in Washington D.C. were doing so “ironically,” he claimed. There were moments, though, when he sounded achingly earnest, as if he were imploring me to understand him in a way that other journalists have failed to do. He offered to take me to lunch the next time he’s in New York. I didn’t say yes, but I also didn’t say no.

I asked about the Halloween party he threw in the fall of 2002. If he were hosting the same party today, would he behave as he had then, welcoming everyone to share in the good time? “I would be the same way at such a party,” he told me. “There’s this sense that if I interact with a black or an Indian, I’ll start yelling at them, and that’s simply not how it is. I’d be the same person I was at that party. But there is something different in my heart.”

Before we hung up, I asked Richard if he’d held his white nationalist beliefs back in Chicago. He said that his views had always been there, in the background, but they were not as urgent as they would become. By the end of the Aughts, he’d decided that the only way to “raise consciousness” was through a kind of horror-show theater—shouting “Hail Trump!” while raising a glass of whisky, for instance. “I’m not suggesting that we lower the marginal tax rate by two percent,” he told me. “I’m suggesting ideas that will change the world. We should be a little scary.”

His answer, like much of our conversation, haunted me for weeks. Just after Christmas, I called him again. I wanted to focus less on the alt right and more on our shared history. We spoke for more than ninety minutes, reminiscing about Chicago and our mutual friends. I reminded him of several of his more provocative statements. He said that everything I remembered—including his comments about Mexican laborers and women—“rings true.”

I asked him why he defended me during that Facebook exchange in 2010, and he replied that he felt he owed it to me, as a friend, to back me up. “We had an experience together, and we’ll probably be connected for the rest of our lives,” he said. “I don’t give up on people like that.” I asked him if he’d ever respected me. He deflected, answering that he has always felt “comfortable with people who are left-wing,” because, “I was never a conservative in the sense that I just wanted to affirm the here and now.”

This led me back to the question of having two separate conversations during those late-night sessions at the pub, if what I’d perceived as irony was, in fact, nothing more than obfuscation. “I was at Chicago,” he replied. “I was learning how to write under persecution, a kind of Straussian way of hiding.” He told me he was “learning the art of lying.”

I asked him about the conversation we had in front of my apartment in the summer of 2008, when he appeared to be shocked that I would date a black woman. “I do remember that situation, and I was a bit flabbergasted,” he confirmed. “But at the same time, I’m also forgiving.” I asked him what he was forgiving me for. “It is what it is, and you are who you are,” he replied. “We’re all trapped in a multicultural, decaying world. It’s not something I’d judge an individual profoundly harshly for, particularly someone I’ve known before and trust.”

Just before we said goodbye, I asked Richard if it would have made any difference if I had been able to see any of this at Chicago and called him out on it, like when I told him he was alienating our classmates. “No, I don’t think so,” he replied. “I’d just tell you I was joking.”

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Six months ago, I set out to try to understand Richard and hopefully to share that understanding with others, much like Peter Maass and Graeme Wood endeavored to do in their pieces. Instead, the question I found myself trying, often painfully, to answer, is why I had remained so tolerant of views I find abhorrent and dangerous, and which Richard never made much effort to hide. Why I had indulged Richard. Why I was always satisfied to take his provocations as jokes.

In reporting this story, I learned that many of the people I remembered being part of that group who stayed late at the pub, knocking back beers and talking about ideas, had in fact grown tired of Richard before we’d even finished our degrees. Had I erred in putting up with him for so long while my classmates kept their distance?

But without wishing to excuse myself for having carried on an eight-year friendship with a white supremacist, my own guilt or innocence now seems almost beside the point. In view of what has happened since our time at Chicago, the more pressing question lies elsewhere: How ought all of us to have engaged with Richard’s illiberal views? Are tolerance and exclusion the only viable options?

At Chicago, we all saw ourselves as model members of a pluralistic society, hungry for debate and willing to consider all opinions. But the truth is that when we caught glimpses of Richard’s true thoughts—when we saw the darkness in him—neither I nor my classmates wanted to see more. If we had been willing to consider his worldview alongside our own, to confront our own tacit assumptions as well as his, perhaps we would have been able to better appreciate his illiberal ideas for the legitimate threat they proved to be. Maybe we would have even been able to persuade him to take a look at the world from our point of view. And maybe not.

But it was far easier to assume he couldn’t be serious.