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  “Hey!” the man shouted, and that wickedness coursed through me even as I marshaled the self-control to turn and walk away, tracking his ever-louder footfalls, leading him toward Seward Park, where at least there were parents and children playing on the slides, New Yorkers who, I hoped, would tend to me if I was knocked to my knees in front of them.

  Moms, I mean.

  “Hey!” he shouted, as we approached the corner, and then, more menacingly, “Asshole!”

  A group of roughhousing boys, quieted perhaps by a real-life scene of what they playacted, turned to look.

  I was embarrassed. I wanted to be held. I wanted to drink tea in a living room warm with sunlight in a world I could understand. I wanted a life I would never again have. I looked at the man with the sweaty forehead and dusty beard, and I let an acidic rage bloom in the place of all I’d lost, coloring my tone such a ragged mess I didn’t recognize my own voice. “I. Did. Not. Take. A. Picture. Of. Your. Fucking. Car.”

  He backed away with his hands up. “Okay, okay,” he mumbled. “Jesus.”

  I leaned against a wall. Something had to change.

  • • •

  In my corner of New York, the masculinity crisis was increasingly taken for granted—something happening to other men, far away.

  “Men keep trying to fight me,” I told my friends, my brother, my coworkers after that day on Orchard Street. Most people shrugged. Weird, they said. What could you do?

  It was 2015, when I began this book, and we were looking toward the future. When I said I was writing about masculinity, people didn’t react as they did at the start of the crisis—more and more, they smiled politely and changed the subject. I understood. A lot of people felt as if we had been talking about a certain kind of man for long enough. It was easier to believe that we lived in the age of progress, and that progress would just keep moving us all forward on its tide. President Obama illuminated the White House in rainbow light, after all, and Beyoncé was on the cover of Vogue’s September issue. Transparent was a critically acclaimed show on Amazon, and Hillary Clinton had just officially announced her intention to become the first woman president of the United States. But underneath the smooth momentum, I could feel the rumbling, like plates moving.

  It occurred to me that maybe it wasn’t just being trans, but the precise timing of my transition that allowed me to see what other people didn’t. The rules that newly defined my life were not futuristic: Do not let yourself be dominated. Do not apologize when you are the one inconvenienced. Do not make your body smaller. Do not smile at strangers. Do not show weakness. The kumbaya narrative of a world without borders, driven by change, wasn’t the whole story. I could see it every day, in the way my body got shaped, read it in the headlines, feel it in the edgy encounters I had with man after man: something terrible was always already happening.

  Maybe, instead of looking for the men you want to be, you need to face your worst fears about who you are.

  Soon enough, nations would be beset by a wave of authoritarian leaders, including the election in the United States of Donald Trump, a man whose campaign for higher office against the first female major party candidate was, in many ways, an open referendum on bodies and the rules regulating them, especially the recent social and political gains made by those whose existence challenged the long reign of white masculinity: women, trans people of all genders, and people of color. Soon enough, a wave of harassment and assault allegations would topple Hollywood executives, actors, and titans of industry. These men weren’t dinosaurs. They were everywhere, all along.

  But back in 2015, in the weeks and months after that day on Orchard Street, as friends shrugged off my question, the crisis within and beyond me continued its slow boil. So I began to look for a new way to shape my own becoming. I was itchy, compelled in the same way I’d felt, pre-testosterone, when I saw a vision of a man bearded and shirtless, sitting at some future kitchen table, and I knew in my gut that it was my destiny to become him.

  Why do men fight? I began to see the question as a proxy, a starting point, for what I initially thought of as a very personal experiment: If I shone a light on the shadowy truths about how I’d come by my own notions of what makes a man, could I change the story of what being a man means?

  Which is how I found myself, less than two months later, boiling a mouthguard in my kitchen, priming it for my bite.

  • • •

  The brutal intimacies of boxing—between coaches and fighters, and even between opponents—are part of our cultural narrative, and I imagined they might help me address the question of male violence with some ritual and containment. I was a longtime fan, fascinated by Mike Tyson’s steroidal press conferences, and the Rumble in the Jungle and the Brawl in Montreal and the War, but mostly by the literary quality to what struck me as a compelling allusion and troubling metaphor for my own experience of manhood: two men, stripped and slowly ground down to their essences in front of a bloodthirsty crowd in a wounding ballet of fists and a losing battle with time. There was an honesty in that violence, a kind of grace that both referenced and eclipsed my more toxic notions of masculinity. I couldn’t think of a more visceral way to face it.

  I’d pitched a feature story about the men who elected to fight in white-collar charity matches, and the guys who trained them, to my bosses at Quartz. Through a buddy who’d done the same fight a couple years before, I signed up to train for a cancer-fighting charity called Haymakers for Hope.

  As I was nervously loading up on sweat-wicking gear and boxing shoes, I couldn’t have guessed how much my struggle with toxic masculinity would eventually lead me to zoom out, asking questions about my own body in space that required me to chase increasingly urgent economic, environmental, and political implications of the masculinity crisis I’d suspected was connected to me, all along.

  But, then again, I had been reading the psychologist Carl Jung, who, after World War II, long consumed by the question of what made people evil, or complicit in evil, settled on a single, elegant explanation. He believed that ostracizing any aspect of the human experience, however ugly, created a “shadow” of our rejected bits that we drag behind us. If we do not see that the shadow belongs to us, we project it onto others, both individually and as a culture. To face and own what most disturbs you about yourself, Jung believed, is among the central moral tasks of being human.

  I began this book because, though I could not articulate it then, I understood that I could not know why I wanted to break that man’s teeth on Orchard Street without understanding, in turn, why he wanted to break mine.

  In pursuit of that night under the bright bulbs of the most famous boxing ring in the world, I spoke to executives and academics, but I also interviewed my siblings, and Jess, and the men who punched me in the face and allowed me to hit them back. I tried to look at masculinity with a beginner’s mind, and I asked questions even when I was embarrassed, or when my mouth was full of blood, or when I was afraid of looking stupid, or lost, or weak. Especially then.

  Why do men fight? This is the story of how I found the answer.

  PART I

  * * *

  Summer

  Five Months until Fight Night

  Am I a Real Man?

  * * *

  Mendez Boxing gym was wedged between anonymous buildings in the Flatiron, under one of those ubiquitous green Manhattan awnings that signal perpetual construction. Though it was just a few blocks north of the office in Union Square where I worked as an editor, I’d never been within a two-block radius—the miracle of living in New York is the way you fashion and refashion each bit of it, until you’ve somehow made it your own. I circled the block, fashioning it, three times before finally heading in, looking foolish in my brand-new Adidas boxing shoes, pulled-high athletic socks, and neon yellow shorts. “Yeah?” the counter guy with the scraggly billy-goat beard said, eyeballing me. I told him I was looking for an acquaintance, Chris Lewarne, a rep from the boxing charity that arranged my fight.
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  He didn’t know who Chris was, he mumbled, but waved me down the stairs. I nodded back, descending into the bowels of the gym and thinking about how I’d gotten the idea from movies that men spent a lot of time in amenable, intimate silences, laced through with well-placed words that telegraphed deep truths, like the pivotal scene in every drama about fathers and sons. I suppose I had indeed spent a lot more time not knowing what to say since my transition. Silence was a kind of defense mechanism, especially in the halting stop-and-start dialogues I found myself muscling through with uncomfortable male relatives, or other people’s fathers.

  I felt the front-desk guy’s eyes on my back as I hustled away. This was the sort of place I would need to be watchful, to be careful to whom I spoke and what I said. I had already decided that I would not tell anyone that I was trans. I’d decided it deep in my lizard brain as I’d circled the block before walking in, or maybe after I first reached out to Chris, or actually when I pitched the story to my bosses at Quartz, or, come to think of it, back when I’d first conceived of writing it. It was not lost on me that I was a historical anomaly, and that it was a function of a wave of newfound goodwill toward trans people that I’d been able to spend the years since I first went on testosterone living openly as a trans man with few negative consequences (and that trans people who were not white or male did not benefit as wholly from this new friendliness and awareness of our lives as I did). Still, I suspected from the moments that I moved anonymously through space that the understanding that my male friends especially had about my body impacted the way they treated me, and my goal was to go undercover, to embed, never mind to stay safe among men who liked to beat each other up for fun.

  In the coming months, that decision would dog me, not least because it highlighted a thorny truth: that, for all the world, I was just another dude in expensive Nikes learning to hit other guys in the face. The relationship between us mostly white men in high-tech training gear with pristine $180 Reyes gloves and the mostly black and brown coaches and (real) fighters using garbage bags to shed water weight wasn’t usually tense, but it was classed. Real boxing gyms, dank spots that were actual training grounds for Golden Gloves champs, were rarely open to gangly newbs like me, but a spate of legendary gyms such as Mendez followed a profitable business model that attracted scrappy Olympic hopefuls, washed-up amateurs looking to become personal trainers or to coach the Next Big Thing, and high-rolling charity fighters alike. I learned quickly that the arrangement had an uneasy economy: amateur boxers tired of the grind could charge white-collar guys (and some women) more than they’d ever make on the fight circuit, and attorneys and hedge-fund managers never forced to expose their bodies to risk of any kind could do so for the thrill and bragging rights.

  Pro boxing hadn’t found a poster child who captured pop culture since Mike Tyson, but the idea of boxing, especially among the hip and well-heeled, had entered a new heyday post–Fight Club. The sport that produced Muhammad Ali increasingly lacked in both heroes and the deeper social narrative of his era, leaving a vacuum eventually filled by a boxing-fitness craze perfect for Instagrammable moments. As I walked through the basement door at Mendez in 2015, it was clear that the latest converts were a certain sort of Wall Street guy, in an extension of the “wellness as luxury” trend that had also launched the spinning craze SoulCycle. (A hedge-fund manager I met at another boxing gym confirmed this. “I would have done blow with a client in the eighties, or gone to a strip club in the nineties,” he said. “But now when I want to impress someone, I take him boxing.”)

  The stink of sweat made my eyes water as I scanned the room, eventually finding my friend Chris, a beefy, smiley Canadian, watching two other white guys in their midthirties pummel each other inelegantly in the ring near the locker rooms.

  “Good work, you guys,” Chris said charitably, chewing on a toothpick. He wore the classic Adidas triple-striped pants, a Haymakers T-shirt, and a light beard, but was the kind of handsome that required zero styling to appear stylish.

  “Thomas!” he said. “I’m so glad you’re here, man.”

  Chris’s fight name was the Cuddly Canadian. I’d seen his photos on social media from his fight two years before and knew he was on the board for Haymakers for Hope, a charity that raised money for cancer research by arranging glitzy bouts between brokers and day traders and venture capitalists with no boxing experience. He was the only reason I had a good shot of getting on the fight card at such short notice—just five months before the event. I was still surprised that my plan had worked, that Quartz had invested in the reporting, that anybody would let a total novice fight in Madison Square Garden with just a few months’ training. But I was still adjusting to the way I’d been treated since I’d transitioned: the ease with which my ideas were often executed, the ways my expertise was assumed before I’d proven it, the serious faces people made when I spoke, the heady faith the world seemed to suddenly have in me.

  To be clear, the Before me wasn’t feminine. I don’t know what it’s like to be wolf-whistled or be told to smile. I was a short-haired tomboy who grew into a swaggering teen, regularly escorted out of women’s rooms by mall security. My younger siblings called me their “big brother,” but underneath my practiced cool, I was still raised to fear men: men in dark streets or clustered outside bars; sketchy drivers; solo figures on park benches or in parked cars or on trains with their hands moving frantically in their laps. I didn’t question this low-grade, persistent anxiety or imagine a world where it didn’t exist. Masculinity was, as far as I was concerned, epitomized by my stepfather, whose years of sexual abuse began when I was four and looking at an anatomy book (“These are boy parts,” he’d said, a simple sentence that separated any notion of my body from his for the next twenty-five years), and the parade of strangers whose threat crowded my days long after the abuse stopped.

  That’s just how guys are, I thought, glad to stand apart from their crassness and bulk, even as my body began to feel estranged from me. So what if I had to cross my eyes to look in a mirror?

  “Men,” Mom said sourly, as we listened to NPR detail Bill Clinton’s infidelity. They were holding us back, the bad dads and the mass murderers and child abusers, the wife beaters and the harassing bosses and the corrupt politicians. Not until I was much older did I realize how complicated her feelings were, that she loved men too, and that her anger was forged in that love: obviously for my brother, and her father, but also for the coworkers that stood up for her, the ex-boyfriends, the civil rights activists she marched alongside in the National Mall, listening to Martin Luther King Jr. announce that he had a dream.

  Decades later, when I first had to tell her who I was, when I asked her to call me Thomas, the memory of the way she’d said “men” replayed on a loop as I dialed. I’d picked the name as an offering, after her brother who’d passed. “I love you,” she’d said, so simple and true, and I’d been so grateful for her, my mother.

  All you need to know about her is that after I transitioned and despite everything, what matters most is that she never said “men” that way to me again.

  • • •

  Chris, a lawyer between full-time jobs, had grown out his hair since I’d last seen him and now worked as Haymakers’ de facto general counsel, riding his motorcycle to various Haymakers-approved gyms, keeping an eye on fighters’ weights and progress, occasionally hopping in the ring himself for fun.

  Bearded and swarthy, standing beside him, I felt like the brainy villain next to the hero in an action movie. “This is going to be awesome!” he reiterated, and I nodded uneasily. Then he introduced me to my potential coach: Errol, an impeccably groomed, bald-headed black dude, who looked at me warily. I wondered, self-consciously, if he presumed me a certain sort of white man, or if his assessment was a colder, more physical one.

  “Have you ever played any sports?” he asked, which didn’t clarify things either way for me, though he seemed a little encouraged when I told him I’d been a goalie, a position
famous for drawing only the truly bananas, a quality I assumed would help me in the ring. This was my inference, of course. Maybe he was just glad to know that a guy that was five feet six inches and 135 pounds wasn’t afraid of getting hit in the face.

  “Let’s get to work,” he said. “Can you run a six-minute mile?”

  Definitely not, I thought. “Probably,” I said.

  Wu-Tang blared over a bell that rang out every three minutes and the constant thwap of men hitting bags, mitts, each other. I did not run a six-minute mile, but I did run three miles in twenty-five minutes, driven by adrenaline and pure terror through a hazing that lasted two grueling hours. Afterward, from the floor, I watched other men’s sweat condense on the ceiling and fought the urge to vomit, feeling proud of myself and strange for feeling proud of myself.

  “You’ve got short arms, but decent strength,” Errol said, from somewhere above me. I couldn’t see him through the sweat stinging my eyes. “I’ll see you tomorrow.” Then he was gone.

  I hauled myself up, and Chris and I sat on the bench kitty-corner to the ring in what actually was companionable silence for a minute or two, but mostly because I couldn’t breathe. We knew each other only vaguely, and mostly from social media. We weren’t, however, actual friends. Not that Chris seemed to make any distinction.

  “You did great,” he said, smiling sunnily. That wasn’t exactly true, but I’d take it.

  “Listen, don’t tell Errol I’m trans, okay?” I asked, once I could catch my breath again.

  He looked at me curiously, but told me not to worry about it. I meant to tell him it was to not compromise my reporting, but a part of me knew that wasn’t exactly true. As we watched a guy across the way do one hundred sit-ups, pause thirty seconds, then do one hundred more, I realized how scared I was. I wore my insistence that I be taken seriously, an inheritance from Before, differently on this body. With nobody challenging me anymore, that drive now just looked like standard-issue male confidence. I felt an acute awareness, sitting next to Chris, of the inches and muscle the other guys had on me, and within their bodies the potential for my own spectacular failure.